Charming Vacation Rentals in Highland Park, IL

2-Acre Highland Park Retreat with Heated Pool ~ 5*
House
2707 Mavor Lane, Highland Park, IL, IL 60035, USA

2-Acre Highland Park Retreat with Heated Pool ~ 5* is located in Highland Park, just 17 miles from Six Flags Great America and 19 miles from Loyola University Chicago. This property offers access to a balcony and free private parking. The pool features a fence and pool views. With free Wifi, this 6-bedroom vacation home offers a cable flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Featuring air conditioning, this unit has a dressing room and a fireplace. The property has an outdoor dining area. Guests can relax in the garden at the property. Wrigley Field is 24 miles from the vacation home, while Lincoln Park Zoo is 26 miles from the property. Chicago O'Hare International Airport is 20 miles away.

Guest Reviews:

- "Ideal place to gather family from around the county to celebrate together." - "10/10, would absolutely stay here again and recommend this place to others" - "Wonderful Home, Close to Everything" - "My family had a wonderful time and loved all the greetings with informational notes. Thank you"

Courtyard by Marriott Chicago Highland Park/Northbrook
Hotel
1505 Lake Cook Road, Highland Park, IL, 60035, USA

Suburban hotel with a 24-hour fitness center and a 24-hour business center
Along with an indoor pool, this smoke-free hotel has a restaurant and a 24-hour fitness center. Free WiFi in public areas and free self parking are also provided. Additionally, a bar/lounge, a snack bar/deli, and a 24-hour business center are onsite.
Housekeeping is available on request.
Courtyard by Marriott Chicago Highland Park/Northbrook offers 149 accommodations with safes and coffee/tea makers. Televisions come with premium cable channels and pay movies.

Bathrooms include shower/tub combinations, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wired and wireless Internet access. Microwaves, refrigerators, and hypo-allergenic bedding can be requested. Housekeeping is provided on request.


Recreational amenities at the hotel include an indoor pool and a 24-hour fitness center.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Great customer service " - "Lots of garbage In the bushes on the east side of the parking lot" - "Will definitely stay here again!" - "Staff was courteous and very hospitable. Location was perfect for our needs. " - "Easy check in. Clean, quiet hotel, well located, people were all friendly. We very much enjoyed our stay." - "Overall it was a great experience. Check was difficult because of staff. Checkout had a 10 minute wait for staff to arrive at the counter, then staff member was not friendly."

Luxury Suite at Private Beach North Shore Residence
House
110 Lakewood Place, IL, IL 60035, USA

Luxury Suite at Private Beach North Shore Residence is located in Highland Park, just a 10-minute walk from Rosewood Beach and 14 miles from Loyola University Chicago. This property offers access to a terrace, free private parking, and free Wifi. Outdoor seating is also available at the guest house. Towels and bed linen are offered in the guest house. The accommodation offers an air conditioning, a heating, and a private bathroom. Luxury Suite at Private Beach North Shore Residence has a garden to relax in after a busy day, along with a private beach area. Wrigley Field is 17 miles from the accommodation, while Six Flags Great America is 20 miles from the property. The nearest airport is Chicago O'Hare International Airport, 21 miles from Luxury Suite at Private Beach North Shore Residence.

Guest Reviews:

- "amazing place and very relaxing" - "Will recommend to others."

Courtyard by Marriott Chicago Deerfield
Hotel
800 Lake Cook Rd, Deerfield, IL, 60015, USA

Suburban hotel with a 24-hour fitness center and a 24-hour front desk
An indoor pool, a restaurant, and a 24-hour fitness center are available at this smoke-free hotel. Free WiFi in public areas and free self parking are also provided. Other amenities include a snack bar/deli, a coffee shop/cafe, and a business center.
Housekeeping is available on request.
Courtyard by Marriott Chicago Deerfield offers 131 accommodations with safes and coffee/tea makers. Rooms open to balconies or patios. Flat-screen televisions come with premium cable channels and pay movies. Bathrooms include shower/tub combinations, complimentary toiletries, and hair dryers.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks and complimentary weekday newspapers, as well as phones; free local calls are provided (restrictions may apply). Hypo-allergenic bedding, change of towels, and change of bedsheets can be requested. Housekeeping is provided on request.


Recreational amenities at the hotel include an indoor pool and a 24-hour fitness center.

Guest Reviews:

- "The best customer service " - "friendly staff clean easy to find family loved it" - "Amazingly Good Hotel " - "Very nice room. Very polite staff. Very clean and comfortable room" - "Very nice staff meet all our needs" - "Great stay" - "No complaints for our 2 day stay enjoyed except for the $11.50 breakfast burrito was not good at all!" - "I loved that it’s not in the middle of everything but a short drive to attractions."

Super 8 by Wyndham Deerfield - Northbrook
Hotel
340 South Waukegan Road, Deerfield, IL, IL 60015, USA

Located in Chicago's northeastern suburbs and 20 minutes' drive from O'Hare International Airport, this Super 8 by Wyndham Deerfield/Northbrook, Illinois offers free WiFi. Super 8 by Wyndham Deerfield/Northbrook is within 3 miles of the Chicago Botanic Gardens and the Ravinia Festival, a summer long music festival. Offices such as Baxter, Caremark and Underwriters Laboratories are nearby. Guests at the Super 8 by Wyndham Deerfield/Northbrook will enjoy amenities such as launderette facilities and free coffee. The comfortable guestrooms offer complimentary amenities such as cable TV and local calls.

Guest Reviews:

- "Very nice stay and very reasonable cost" - "I like it but not enough Taos in the room" - "comfy and very adorable would definitely come back" - "Pretty much what you'd expect ..." - "Great value for the price. Would stay there again." - "Well, if I had gotten a cold from it being so cold in the room, it was ok" - "Great value for money" - "A great value for a clean place to sleep. And very friendly and helpful desk people."

Residence Inn By Marriott Chicago Deerfield
Hotel
530 Lake Cook Rd, Deerfield, IL, 60015, USA

Suburban hotel with free breakfast and a 24-hour fitness center
Along with a 24-hour fitness center, this smoke-free hotel has a snack bar/deli and a 24-hour business center. Free full breakfast is provided, as well as free WiFi in public areas, free self parking, and a free manager's reception. Additionally, coffee/tea in a common area, a seasonal outdoor pool, and a business center are onsite.
Housekeeping is available on request.
Residence Inn By Marriott Chicago Deerfield offers 128 accommodations, which are accessible via exterior corridors and feature coffee/tea makers and hair dryers. Accommodations have separate sitting areas and are furnished with double sofa beds. Smart televisions come with premium cable channels and Netflix. Accommodations at this 3-star hotel have kitchens with full-sized refrigerators/freezers, stovetops, microwaves, and cookware/dishes/utensils. Rooms have partially open bathrooms. Bathrooms include shower/tub combinations and complimentary toiletries.

This Deerfield hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and phones. Change of towels and change of bedsheets can be requested. Housekeeping is provided on request.


Recreational amenities at the hotel include a 24-hour fitness center and a seasonal outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "This was a clean and easy pleace to stay. Super comfortable. The in room kitchen was super convient. Bed and couch were super comfortable. " - "Great overall" - "Excellent Stay for a quiet get away with your spouse. " - "• This property is in the middle of office buildings so it is so very quiet and safe. • The staff is friendly, efficient, and accommodating. • The breakfast buffet is more than adequate with both hot and cold selections. Of course it's not Michelin quality fare but it totally gets you going in the morning. • Location is not really walking distance to restaurants and stores but you didn't walk to the hotel, did you? • Hotel is freeway close and only 17 miles to O'Hare • The Pickle Ball court was a popular amenity and I'm sure the BBQ is also well-used in warmer weather."

Courtyard Chicago Highland Park/Northbrook
Hotel
1505 Lake Cook Road, Highland Park, IL, IL 60035, USA

Located 15 miles from Loyola University Chicago, Courtyard Chicago Highland Park/Northbrook offers 3-star accommodations in Highland Park and has a shared lounge, a restaurant and a bar. The property is around 19 miles from Six Flags Great America, 20 miles from Wrigley Field and 21 miles from Lincoln Park Zoo. The hotel features an indoor pool, a 24-hour front desk and free WiFi throughout the property. Guest rooms in the hotel are equipped with a flat-screen TV with cable channels. All rooms at Courtyard Chicago Highland Park/Northbrook have air conditioning and a desk. Guests at the accommodation will be able to enjoy activities in and around Highland Park, like cycling. Courtyard Chicago Highland Park/Northbrook also provides a business center and guests can use the on-site ATM machine at the hotel. United Center is 23 miles from Courtyard Chicago Highland Park/Northbrook, while Union Station is 23 miles from the property. Chicago O'Hare International Airport is 18 miles away.

Guest Reviews:

- "Comfortable stay at a Courtyard in Highland Park" - "A nice surprise at a Marriott hotel" - "Very enjoyable stay." - "An amazing time and would most definitely be back." - "Northbrook Excellence" - "I got a great night’s rest." - "Perfect Spot" - "Super super clean and Great bed." - "It’s a decent quick overnight stay." - "We enjoyed staying at this hotel" - "Dependable, safe, clean location." - "Good hotel but very far from downtown Chicago"

Super 8 by Wyndham Deerfield/Northbrook
Hotel
340 South Waukegan Road, Deerfield, IL, 60062, USA

Hotel in Deerfield with free breakfast and a 24-hour front desk
Along with coffee/tea in a common area, this smoke-free hotel has laundry facilities and a 24-hour front desk. Free on-the-go breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, a TV in a common area, a front-desk safe, and a banquet hall are onsite.
Super 8 by Wyndham Deerfield/Northbrook offers 117 accommodations, which are accessible via exterior corridors and feature complimentary toiletries and blackout drapes/curtains. Flat-screen televisions come with premium cable channels.

This Deerfield hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and desk chairs, as well as phones; local and long-distance calls are complimentary (restrictions may apply). Housekeeping is provided daily.

Guest Reviews:

- "I live in Wisconsin now where the streets roll up at 8pm and I loved the 3rd floor view out on the balcony of 94! My room was clean and I enjoyed it. May I suggest you turn the hot water temp down because that temp was scalding & dangerous, just too hot. Thank you" - "Everything went easy and quickly and the room was clean " - "Great people" - "Cheap room but clean and quite enough." - "This was a very nice and clean hotel for Chicago suburbs at an affordable price. I had a prior experience with Red Roof+ which was GOOD and CLEAN beyond my expectations and this one didn’t disappoint either. They gave good snacks too at check in. Ours was upgraded premium room #205."

Courtyard Chicago Deerfield
Hotel
800 Lake Cook Road, Deerfield, IL, IL 60015, USA

Located in Deerfield, 17 miles from Loyola University Chicago, Courtyard Chicago Deerfield has accommodations with a garden, free private parking, a shared lounge and a restaurant. This 3-star hotel offers a 24-hour front desk, an ATM and free WiFi. The hotel has an indoor pool and a business center. An American breakfast is available at the hotel. Courtyard Chicago Deerfield has a sun terrace. Six Flags Great America is 19 miles from the accommodation, while Wrigley Field is 22 miles from the property. Chicago O'Hare International Airport is 16 miles away.

Guest Reviews:

- "thank you" - "Large, quiet hotel in a safe Chicago suburb close to amenities" - "Great Hotel" - "All went well." - "Excellent" - "Perfect stay." - "Great location, Quiet and nice" - "Nice stay" - "Quiet, spacious, comfortable room with courtyard view!" - "Will return" - "It was great. The staff was very friendly and accommodating. Would recommend." - "Convenient location" - "Fabulous. My sister and I liked it!"

Stunning & Stylish Downtown Studio - Highland Park
Apartment
Highland Park, Illinois, USA

Experience the charm of downtown Highland Park, IL, in our newly-remodeled, stylish studio apartment steps from the Metra train! Our space boasts a modern design with two large skylights for natural light and unparalleled comfort. Discover local shops, eateries, and galleries, enjoy nearby shorelines and beaches, then retreat to this luxurious yet cozy home-away-from-home. Start your Highland Park adventure today!

Guest Reviews:

- "Everything was as described. Parking is secure. Location is quiet, inside a nice neighborhood " - "Complete with stove from the 1970s. But it's very clean so I was comfortable for the most part. The area is also convenient. I would return if ever back in the area."

Residence Inn Chicago Deerfield
Hotel
530 Lake Cook Road, Deerfield, IL, IL 60015, USA

Located in Deerfield and with Loyola University Chicago reachable within 17 miles, Residence Inn Chicago Deerfield has express check-in and check-out, non-smoking rooms, free bikes, free WiFi throughout the property and a garden. This 3-star hotel offers a 24-hour front desk and a business center. The hotel provides an outdoor swimming pool and free shuttle service. All rooms at the hotel come with air conditioning, a seating area, a flat-screen TV with satellite channels, a kitchen, a dining area and a private bathroom with free toiletries, a shower and a hairdryer. All guest rooms will provide guests with a desk and a coffee machine. Residence Inn Chicago Deerfield offers a buffet or American breakfast. Six Flags Great America is 20 miles from the accommodation, while Wrigley Field is 22 miles from the property. Chicago O'Hare International Airport is 16 miles away.

Guest Reviews:

- "Amazing" - "Very comfortable" - "Perfect spot to stay a couple of days, the kitchen makes things super manageable throughout the week as well as the incl" - "I would stay next time, when I come to UL for business" - "This was a.cute, comfy stay with a subdivision feel that was dog friendly." - "Great Hotel" - "Excellent large apartment with all amenities" - "Excellent" - "Pleasant surprise for a suburban residency property."

The Sunset Manor - Luxe Mansion for Serene retreat
House
Highland Park, Illinois, USA

Welcome to Sunset Manor, a luxurious 6-bedroom, 4.5-bathroom residence where elegance and comfort come together to create unforgettable memories. Located in the prestigious Northshore neighborhood of Highland Park, this sophisticated retreat is perfect for families or groups, offering modern amenities, stylish details, and a peaceful escape. Relax in the hot tub, entertain in the beautifully designed spaces, or explore nearby landmarks, including the iconic gates of Michael Jordan’s neighborhood estate. Sunset Manor is the perfect backdrop for your next getaway.
The chic design and extensive amenities are sure to impress.

★ HIGHLIGHTS ★
✔ 6 Cozy Bedrooms
✔ Multiple Living Areas
✔ Play room for Kids
✔ Full Kitchen & Dining Area
✔ Full Bar Area
✔ Theater room & Game area
✔ Hot Tub
✔ High speed Wi-Fi
✔ Free Driveway parking
✔ Pack-N-Play & Highchair Provided

The Space:
Welcome to your dream vacation rental! This exceptional home offers the ultimate blend of relaxation and entertainment, making it the perfect choice for families and groups.

Spacious Living Room: As you enter, you’ll be greeted by a beautifully designed living room featuring high ceilings, a contemporary art wall, and a large TV. It’s the perfect space to unwind and feel at home.

Family-Friendly Kitchen and Dining: On the same level, enjoy a modern, fully-equipped kitchen with a cozy breakfast nook and an adjacent dining room—ideal for family meals and gatherings.

Fun Playroom for Kids: Our home is perfect for families, with a dedicated playroom designed to entertain younger children. It includes an indoor play set, pretend kitchen, TV, and comfy furniture, ensuring hours of fun and engagement.

Bar & Entertainment Area: Just a few steps up, you’ll find a sophisticated full bar area complete with plush seating and a foosball table. It’s the ultimate space for adults to relax, enjoy drinks, and have lively conversations. We have a TV at bar area to watch sports.

Home Theater and Game Room: Descend to the basement where a luxurious theater room awaits. Enjoy your favorite movies on a cozy sectional, and challenge friends to a game of pool. For fitness enthusiasts, there’s also workout equipment available.

Perfect for Relaxation and Fun: This home is designed with comfort and entertainment in mind, making it an ideal choice for a memorable family vacation, a group getaway, or a relaxing retreat. Book now to enjoy a stay in this top-rated vacation rental!

Stunning Kitchen & Elegant Dining Areas: Perfect for Culinary Creations and Entertaining
This beautifully decorated kitchen is the heart of the home, featuring spacious countertops, ample cabinetry, and modern appliances that make cooking both easy and enjoyable. The breakfast nook and dining table offer plenty of seating for the whole family. Enjoy the convenience of a local coffee station, perfect for savoring the best brews.
✔ Eat at the Kitchen with breakfast nook
✔ Coffee Machine
✔ Hot water Kettle, Microwave, Toaster & Blender
✔ Stainless Steel Appliances
✔ Dining room with Seating for 8
✔ Cooking & Dining Essentials

Tranquil Bedrooms & Serene Bathrooms: Your Private Retreat Awaits
♛ Bedroom 1 (Master Bedroom)
✔ King Size Bed with Nightstands
✔ Memory Foam Mattress
✔ Accent Chairs to Relax
✔ Closets for Storage
✔ Standing Mirror

♛ Bedroom 2
✔Queen Size Bed with Nightstands
✔ Closet for Storage

♛ Bedroom 3
✔ 2 Bunk beds (Sleeps 4) with a Nightstand
✔ Closet for Storage

♛ Bedroom 4
✔ Twin Size Beds (Two) with Nightstands
✔ Closets for Storage

♛ Bedroom 5
✔ Full Bed with Night stand
✔ Closet

♛ Bedroom 6
✔ Full Bed with Night stand
✔ Closet

🛏Additional Sleeping
✔ Pack-N-Play Provided

🛁Master Bathroom
✔ Stand Up Shower
✔ Soak in Tub
✔ Toilet & Floating Double Vanity
✔ Soap & Shampoo

🛁Bathroom 2
✔ Shower Tub
✔ Toilet & Vanity
✔ Soap & Shampoo

🛁Bathroom 3
✔ Stand Up Shower
✔ Toilet & Floating Vanity
✔ Soap & Shampoo

🛁Bathroom 4
✔ Stand Up Shower & Steam
✔ Toilet & Floating Vanity
✔ Soap & Shampoo

Powder Room
✔ Toilet & Floating Vanity

IDEAL FOR FAMILIES:
✔ Quiet Neighborhood
✔ Large Yard
✔ Pack-N-Play
✔ Highchair
✔ Games for Kids & Reading Material

Prime Location with Exceptional Connectivity:
Nestled in a highly walkable neighborhood, this property is adjacent to Sleepy Hollow Park, offering scenic walking paths. Just minutes away is Danny Cunniff Park, featuring a range of sports and recreational activities, including the Centennial Ice Arena. The Fort Sheridan Metra Station, a quick 6-minute drive, ensures easy access to downtown Chicago and beyond. Additionally, enjoy convenient drives to Naval Station Great Lakes (19 minutes), Ravinia Festival (16 minutes), Chicago Botanic Garden (11 minutes), and Rosewood Beach (13 minutes).
(distances in time are calculated considering travel by car)

Guest Access:
Guests have access to the entire home, with the exception of a locked supply closet & storage room.

Other things to note:
No events or parties are allowed.
Sometimes we might require a security deposit and/or proof of ID to validate the guest name and age to protect both host & the guest.

Amenities:

Air Conditioner • Security/Safety • Laundry • Hot Tub • Child Friendly • Kitchen • Fireplace/Heating • Balcony/Terrace • Tv • Wellness Facilities • Bedding/Linens • Internet

Modern Luxe Home w/Gameroom and Electric Fireplace
House
Highland Park, Illinois, USA

Welcome to our sophisticated ranch-style home, nestled in the serene Chicago’s north shore neighborhood of Highland Park. This carefully curated residence offers a peaceful retreat in a walkable neighborhood with convenient access to dining, Trails to Lake Michigan, Metra to downtown Chicago and many more.

Step inside and discover an oasis of elegance and comfort. The interior boasts tasteful decor, comfortable furnishings, and modern amenities, creating a haven of relaxation and style. Whether you're savoring a cup of coffee on the private patio or venturing out to explore the area, this home provides the perfect backdrop for a memorable vacation experience.

ABOUT THE SPACE
★ HIGHLIGHTS ★
✔ 4 Cozy Bedrooms: 5 Beds, 3 Full Bathrooms plus 2 Fultons
✔ 2 Living rooms with TV’s
✔ Renovated space
✔ Open concept Living area, Stocked Kitchen & Dining
✔ High speed Wi-Fi
✔ Free Driveway parking
✔ Pack-N-Play & Highchair Provided

ENTERTAINING LIVING ROOM
Relax and watch your favorite show or movie with our 55° Smart TV, laugh and compete with our collection of board games, challenge each other with a puzzle, take a moment to browse our books and magazines, but most importantly, create everlasting memories with your friends and family in this beautiful home.
✔ 55 inch Smart TV - Includes apps like Netflix, Prime, etc in Living room & Family room
✔ Cozy Fulton, Sofas & Lounge Chairs in Living & Family room with electric fireplace
✔ Coffee Table
✔ Office Desk
✔ Games, Reading Material
✔ Game area with Table Tennis, Air Hockey, Indoor Basketball

STOCKED KITCHEN & DINING
Spacious countertops, ample cabinetry, and modern cooking appliances make for an easy and creative time in the center of this home. There is plenty of seating for the whole family featured at the breakfast nook and the dining table. Take advantage of the local coffee station, boasting the best brews. Enjoy your favorite wine served chilled using a wine chiller.
✔ Eat at the Kitchen Island, seating for 4
✔ Coffee Machine
✔ Hot water Kettle, Microwave, Toaster & Blender
✔ Wine Chiller
✔ Stainless Steel Appliances
✔ Dining Table with Seating for 6
✔ Cooking & Dining Essentials

RELAXING BEDROOMS & BATHROOMS
🛏Bedroom 1 (Master Bedroom)
✔ King Size Bed with Nightstands
✔ Memory Foam Mattress
✔ Closets for Storage
✔ Standing Mirror

🛏Bedroom 2
✔Queen Size Bed with Nightstands
✔ Office Desk & Chair
✔ Closet for Storage

🛏Bedroom 3
✔ Double size Bed with Nightstands
✔ Closet for Storage

🛏Bedroom 4
✔ Twin Size Beds (Two) with Nightstands
✔ Closets for Storage

🛁Master Bathroom
✔ Stand Up Shower
✔ Toilet & Floating Vanity
✔ Soap & Shampoo

🛁Bathroom 2
✔ Shower Tub
✔ Toilet & Floating Vanity
✔ Soap & Shampoo

🛁Bathroom 3
✔ Stand Up Shower
✔ Toilet & Vanity
✔ Soap & Shampoo

IDEAL FOR FAMILIES
✔ Quiet Neighborhood
✔ Large Yard
✔ Pack-N-Play
✔ Highchair
✔ Games for Kids & Reading Material

ABOUT AREA
Neighborhood is highly walk friendly with Fort Sheridan Trails leading to Lake Michigan. Few minutes away from Highwood Downtown with Great Places to Eat & Entertain. Metra Station a Block away which goes to Downtown Chicago and Surrounding Areas with great Connectivity. 15 Minutes drive to Naval Station Great Lakes. 14 Minutes drive to Ravinia Festival. 11 Minutes drive to Chicago Botanic Garden. 13 Minutes drive to Rosewood Beach.

Guest Access
Guests have access to the entire home, with the exception of a locked supply closet & storage room.

Other things to note
No events or parties are allowed.
Sometimes we might require a security deposit and/or proof of ID to validate the guest name and age to protect both host & the guest.

Guest Reviews:

- "In town for a surprise birthday party for our brother, siblings stayed here and the house worked well for our group." - "The pictures were nice but the house did not align with the pictures. The exterior was filled with cobwebs, there was no mulch around the landscaping, and the exterior lights did not work. The entry lights (inside the house) also did not work. The towels had been folded up wet and smelled musty. Pillow cases were also wet. The lights in the basement laundry room didn't work so had to use cell phone to see. A partial roll of toilet paper was left in a bathroom with what appeared like blood or feces on it and there was what appeared to be pet urine on the corner of the bed skirts. Sheets also did not fit the bed size so popped off the mattress. The manager was prompt to respond and attempted to send new sheets, towels and toilet paper. However, the products were delivered to the wrong address. I asked to be let out of the stay and my request was denied. "

Serene Retreat Awaits You!
House
Highland Park, Illinois, USA

Set in the midst of an affluent neighborhood, this spacious and sunny four bedroom retreat offers all the comforts of a home away from home. With it's perfect location close to Lake Michigan, Chicago Botanical Garden, Ravinia, Naval Base, and Six Flags Great America to name a few, our family home is within reach to Chicago as well. If you feel very adventurous, just leave your car in garage, pick up a bike and ride the Lake Shore Bike trail all the way to downtown Chicago, enjoying the beautiful scenery. If you feel less adventures but still would like to enjoy beautiful scenery, you can do it by taking a train. Metra can get you downtown Chicago in less than 45 min. and the stop is within walking distance.

Guest Reviews:

- "Great for proximity to Highland Park activities. Our friends live less than 10 minutes from the property and it is close to downtown HP and train into the city. There were 2 couples and one single and plenty of room for all. Property was clean and spacious. Would stay again." - "The twin beds need new mattresses. Other than that, very comfortable weekend for the family." - "Particularly appreciated for this 7-night stay were the hosts' gracious manner, informative messages, and prompt response to questions. The home's highlights include its large dining room table, comfortable lower-level family room w/ large screen TV, spacious laundry room, and 2-car garage. The home's location is quiet yet provides quick access to major transportation routes. Overall, the home is well-appointed, welcoming, and comfortable. Would rent again."

Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
Cottage
Highland Park, Illinois, USA

Escape the city and relax in our newly renovated historic cottage and gardens. Peaceful yet centrally located, vintage yet modern, Mere Cottage has so much to offer.

Inside:
You'll enjoy updated amenities in harmony with a distinctive vintage charm. The common area has an open layout, perfect for socializing. The kitchen and pantry (my favorite room!) are new from top to bottom and are fully stocked with any cooking gadgets you may need. Two bedrooms are joined by a Jack & Jill bathroom. The living room has a sofa that pulls out into full size bed.

Outside:
Jordan and I had fun redesigning the grounds from front to back. Enjoy the front garden from the rocking chair on our wrap around porch. Out back we've added a vegetable and perennial garden for you to take in. Dinner out on the back deck overlooking the garden is highly recommended!

Location:
Our cottage is located in Highland Park, about 25 miles north of Chicago on Lake Michigan. We like to think we have the best of both worlds- being in a quiet residential neighborhood with walking access to numerous amenities right around the corner. We're a quick 5 minute walk to Highwood (the north shore’s restaurant district) and an 8 minute walk to the Metra train that can take you from Chicago to Kenosha and any place in between. We're also right on the North Shore bike path (bring your bikes!). Fort Sheridan is also close by and worth exploring for its interesting history, architecture, and nature trails.

Getting around
On foot:
Many errands can be done on foot. We have some of the best restaurants and watering holes north of Chicago within walking distance. There is also a Walgreens convenience store 2 blocks away.

By car:
Getting around by car is also easy. Parking is readily available almost anywhere you'll visit. You can get to downtown Chicago in 30 minutes in ideal traffic.

Train:
The Metra (our train system) can also conveniently get you to and from various attractions including downtown Chicago (a scenic 45 minute ride), Ravinia music venue, the Chicago Botanic Gardens, Great Lakes Naval Base and many more.

Bike:
Pack your bikes! We're located on the north shore bike trail. Head north on the trail to check out the beautiful Fort Sheridan, Lake Forest, and quaint Lake Bluff. Head south to Ravinia, Chicago Botanic Garden, and numerous other beautiful villages along Lake Michigan. I bike often and will gladly point you to some great hidden gems!

If you're flying into O'hare, we recommend taking an Uber to our cottage. We're about a 30 minute drive from the airport.

Six Flags Great America is also a 25 minute drive away.

Guest Reviews:

- "This place is legit. We had great communication with the host (Daniel) before arrival. He was quick to respond to questions and very helpful. On arrival, it was apparent that they take great pride in their home. The gardens are absolutely beautiful. The front porch was darling and the keyless entry made it super easy to get in. The place is decorated so nicely. The set up is perfect. We used it as a home base for visiting friends and it made it a great place to relax before and after heading out. Comfy beds, nice sheets and towels, and although we brought our pwn pillows, theirs seemed to be good. The back deck is perfect for having some morning coffee or evening drinks. The garden back there was a mix of vegetables and flowers. My friends took note and said they wanted to do similar things to their place. The kitchen was clean and had everything you could want. Even the quality of the glassware was impressive. The hosts live across the street and are very friendly and helpful. We enjoyed speaking with them and they gave some good suggestions. You can't beat the location. Walkable to many restaurants, bars and shops. The town is just really cute and very easy to get around. I can't say enough good things about our stay. Next time we are visiting our friends, we are most certainly going to stay here again."

Chic Studio - In Downtown Highland Park, by Metra
Apartment
Highland Park, Illinois, USA

Welcome to our beautiful and elegant studio apartment located in the heart of downtown Highland Park. Our space is perfect for couples, concert-goers, and families of two who want to explore the area and enjoy all the creature comforts of a clean, modern space. Our apartment features a soft and comfortable queen bed, and even though this apartment does not have a window, it does have ceiling skylight window that brings in plenty of natural light, and a very clean bathroom stocked with all the essentials.

Our building is conveniently located near many attractions, including the famous Ravinia Festival, a beautiful outdoor music venue that hosts world-class performers. You can also explore the beautiful shores of Lake Michigan, just a short drive away, where you can enjoy swimming, sunbathing, and scenic views.

If you're looking to explore the area, the nearby Metra station provides easy access to downtown Chicago and all its famous landmarks. Additionally, our location is close enough to the Great Lakes Naval Station for easy access, yet far enough away to avoid any noise or traffic disruptions.

When you're not out exploring, our studio apartment provides a relaxing oasis. You can unwind on our comfortable furniture, catch up on your favorite shows with our smart TV, or take advantage of the free Wi-Fi. Our fully stocked kitchen has everything you need to prepare meals, and we also provide coffee and tea to help you start your day off right.

Book your stay at our beautiful Highland Park studio apartment today and enjoy a comfortable and convenient experience.

Guest Reviews:

- "Excellent location. Well kept." - "Great little place for us to stay and enjoy our time in quaint Highland Park. So EASY to walk everywhere. Catch the train and it’s easy access to the other suburbs or the City. We enjoyed our time very much." - "Overall my husband and I were happy with the studio apt. Communication with the host was easy and the place was clean and had all the amenities we needed during our stay. The place was centrally located with easy access to shops/restaurants as well as the Metra system to take us into Chicago. The one drawback is that there are no windows but the skylight adds enough natural light to the space and we were there to sightsee and not stay for extended periods in the apartment."

Modern Luxe home w\/Gameroom and Electric Fireplace
House
Highland Park, Illinois, USA

Have fun with the whole family at this stylish place. Enjoy the game room equipped with everything you need to have a memorable night! Pool table, ping pong table, and more board games!

This beautifully renovated home has 4 spacious bedrooms, 3 baths, family room, dining room, electric fire place, updated kitchen, and lovely patio.

Get to downtown Chicago in 40 min via the Metra or car. The metra station is minutes away walking distance!

Our charming & relaxing home is modern and has a finished basement equipped with a pool table in the basement, with a foldable ping pong table and 55inch TV that makes it perfect for kids to lounge and have fun. All parts of the house is perfect to lounge and relax in, the space is well decorated with a large open space concept in the dining room and fireplace with a family room.

Equipped with high speed wifi, large 65 inch Roku Smart flat-screen TV (made easy for streaming Netflix, Amazon Prime, Hulu, Disney Plus, etc), heating, AC, washer & dryer plus 1-car garage parking with space for 4 cars to be parked on driveway.

We also have a fully stocked kitchen with blender, coffee, toaster, refrigerator, oven, stove, and dishwasher. All new appliances.

The master bedroom has a luxurious king bed and there are blinds in every room.

The 2nd bedroom has a queen bed, blinds, and a workspace.

The 3rd bedroom includes a queen bed and blinds
The fourth bedroom has two twin beds perfect for kids.

All of our bedrooms have the softest memory foam mattresses and fluffiest pillows that makes sleeping its own sanctuary!

-- Pool table in the house is currently unavailable temporarily, we are working on restoring it and will be back available in near future. The upside for that is you now have more space to entertain your guests that can be used for variety of options.

Additional rules
Note : The ONLY outdoor areas of the property is being monitored by cameras. The cameras or wi-fi should always be connected, if lost our connection we require your support to connect them back again. Any violations are subject to fine. This is in place for the safety of our guests and property. We require a refundable security deposit during the check-in process.

Guest Reviews:

- "Host was super helpful & insightful to our needs. Our leadership team stayed together for our first time to do some team building. House provided plenty of sleeping spaces, great "separate" spaces and great common spaces. The accommodation worked incredibly great for our group. As an added bonus, the check out process was incredibly easy. I would definitely stay again!" - "We came to Chicago for our new Sailor. The house was exquisite. Everyone was comfortable because there is soooo much room. The design is extremely well thought through. I cooked throughout the day and we went to restaurants at night. The sheets were smoothe and all the throws were comfy. The owner was excellent. If ever I was to return, this is where we would stay. Do not miss out, seriously book this house for your next vacation."

Chic Studio in Downtown Highland Park near Metra
Apartment
Highland Park, Illinois, USA

Welcome to downtown Highland Park! Experience comfort and convenience in our cozy studio apartment with FREE parking. Just a 5-minute walk to the Metra, and within a leisurely 15-minute stroll, enjoy breathtaking views of Lake Michigan. Explore historic Fort Sheridan Forest Preserve and beach, only a quick 5-minute drive away. Discover delightful dining, gelato shops, parks, and more—all within walking distance. Our well-appointed apartment ensures a memorable stay in this vibrant neighborhood.

Guest Reviews:

- "The property was just as described. There are so many restaurants and shops right outside the door. Yet also quiet. Perfect if you are also seeking train access. " - "Overall everything was great. Super clean exept the bowls in the kitchen were a little dirty. First message i sent to the property manager did not get answered for multiple hours so I had to message them again. After the second message communication was great. I had a great stay at this place."

Near Ravinia and Navy Base, charming 3-bedroom house in peaceful Highland Park
House
Highland Park, Illinois, USA

Modern 3-bed, 4-bath home in Highland Park, IL, steps from Ravinia Festival. Recently renovated with an open-concept living area, gourmet kitchen, and stylish, comfortable bedrooms. Ideal for families, with easy access to downtown shops, cafes, and parks. Perfect for relaxing after concerts or exploring local charm. Book your stay for a memorable experience!

★ LOUNGE ★
Lounge in a large airy comfortable living room or the basement, both equipped with smart TVs. Basement also has a foosball table.

★ KITCHEN ★
Need a break from the amazing local restaurants? The kitchen is stocked with utensils, glassware, cutlery, pots and pans; everything one would need to fully utilize the kitchen and make a home cooked meal. Full sized fridge and freezer. Drip coffee maker and toaster available as well.

★ BEDROOMS ★
Ready to rest and relax from all the Chicago adventures? Each bedroom is beautifully furnished with comfortable mattresses and plenty of storage for clothes. Hangers provided. Air mattress available by request.

★ BATHROOMS ★
There are four full bathrooms stocked with fresh towels and essential toiletries for your convenience (shampoo, conditioner, body wash and lotion). The master suite bathroom features a walk-in shower, while two other bathrooms include a soaking tub offering perfect spa-like relaxation.

★ PARKING ★
Two spots available in the driveway.

★ PETS ★
While we love our furry family members, we unfortunately do not allow pets.

★ Easy Check-In Process for your rental agreement, ID verification, & security hold

It’s just like when you check in at a hotel and give your ID and security deposit to the front desk, except our front desk is online! It's super easy to complete on your phone! We use a web-based system called Happy Guest, and you’ll receive a personalized rental agreement, ID verification, and a simple security hold (which is not a security deposit) to receive your arrival instructions. It’s simple: finish these steps, and you’re all set to enjoy your stay! Note: arrival info won’t be sent without completing these steps, and refunds aren’t possible if skipped. Your personalized guidebook will give you all the info about the home, my favorite local spots, automatic early check-in notifications, and sometimes even late checkout! You can even share it with friends and family! Got questions? Just message us anytime!

Guest Reviews:

- "We booked this house to tour a university and to get to know the area. Plenty of (clean!) space for the four of us (parents and 2 adult sized children) to clean up and rest after a long day of exploration. The house is located in a quiet and pretty neighborhood with plenty of good food and the shore nearby. Lori was a wonderful and informative host! Totally recommend this property and would book again if we're in the area. " - "The host Lori was very nice and helpful."

Condo - Downtown Highland Park
Condo
Highland Park, Illinois, USA

Completely gutted and exquisitely remodeled in 2015, this quiet 10-unit, two-story building shines like its neighboring upscale condo properties. Interiors sparkle with marble counter tops in kitchen and baths. Designer cabinetry and fixtures complement the wood floors throughout the unit. Bathrooms have tasteful Italian tiles on floors and in tub/shower area. New, double-pane windows keep utility bills low and let in lots of natural light. Central heat and air and in-unit, full-size washer-dryer perform highly efficiently. Master bedroom has its own bath. Top-of-the-line brushed steel appliances in the kitchen lend a contemporary touch. Subtle paint colors are accented with white wood trim. This is not only a place to hang your hat, it’s a place to enjoy a pleasant lifestyle.

Here are a few more outstanding features:
• Off-street parking
• 5-minute walk to Metra Highland Park station (easy 40 – 60-minute trips to Ogilvy Transportation Center)
• 8-minute drive to Highway 41/I-94
• 10-minute drive to Highland Park Hospital
• Secure exterior entry to interior units
• Walking distance to chic shops, notable eateries, salons, the village library and several specialty gyms
• Forget the hassle of driving and parking at the Ravinia Festival in the summer—you’re steps from the Ravinia shuttles
• Miles of walking and cycling trails
• Beautiful architectural gems throughout the neighborhood; excellent walking areas
• Short drive to beautiful Rosewood Beach
• Short walk to breath-taking views of Lake Michigan
• Responsive, caring owner
• Each unit is individually metered for electric; tenant pays for Wi-Fi
• Online rent payment portal/app
• Building, surrounding yard, sidewalks and parking lot well maintained in all seasons
• Friendly long-term tenants

Guest Reviews:

- "We loved our stay in Highlands Park. The place was updated and well stocked. The location was great. Check in was easy. We will definitely stay here again!!" - "We were thankful to find this place! It fit our needs perfectly, had a great location, and was reasonably priced. We would definitely stay here again if we needed to."

Safe & Secure Parkview-Sleep Sanctuary+Kitchen
Apartment
Highland Park, Illinois, USA

Perfect location, close to everything and quiet. Charming apartment with designer touches overlooking a park and just a 10-minute walk to Rosewood Beach on Lake Michigan. Our centrally-located studio apartment has everything you need to call it home—full size kitchen amenities, small appliances, and full bathroom with lots of hot water, very quiet. No neighbors above or below. Very cozzzy!

Free lot parking (must provide license plate), free shared laundry, and Walgreens steps away

Amenities:

Wellness Facilities • Bedding/Linens • Internet • Air Conditioner • Security/Safety • Pet Friendly • Kitchen • Other • Laundry • Fireplace/Heating

Cute Ranch House close to town monthly stay
House
Deerfield, Illinois, USA

Newly remodeled and beautifully furnished ranch house with 3 bed and 2 bath (1 bathroom is in basement) can sleep 6. Huge unfinished basement and 1 car attached garage. Walking distance to Deerfield's robust downtown, train, library, dining. All essential amenities included (utilities, wifi, smart TVs, cooking needs, etc.). Deerfield offers the comfortable suburban lifestyle while also being conveniently close to downtown Chicago. Central AC and furnace.

Guest Reviews:

- "For the most part the house suited our needs BUT it was dirty, animal hair & cat toys behind the couch & under beds, throw rugs dirty & covered with animal hair, stove & oven greasy, basement utility sinks & mops grossly dirty. This house is in a great location but needs a thorough cleaning."

Picturesque! Mid Mod Home - 20min from Chicago!
House
Highland Park, Illinois, USA

Enjoy our Adorable, Mid Century Modern home with serene pollinator gardens, A+ rated schools and parks, hospital networks, and central highways to Chicago and surrounding suburbs! You'll love this 3 bed, 1 bath home with new washer/dryer, stainless steel appliances, and décor to help you feel at home. Pets Welcome!

Guest Reviews:

- "Great home near west ridge park! We needed a place to stay after our home sold quicker than anticipated. Great home and hosts."

Entire home, close to Ravinia Festival, Lake, Town, and Train to the city.
Cottage
Highland Park, Illinois, USA

Your Highland Park R&R plus adventures begin & launch from this vintage, historical, 3-bedroom eco-cottage. Built originally as an ornithologist’s {*bird lover’s} cottage… Each bedroom offers a cozy retreat — each replete with far infrared heat source & dedicated air purifier — plus a queen, two twins, and full bed {*boasting silky smooth bamboo bedding, along with adjoining Down Comforters & Pillows}, respectively. Enjoy the convenience of a fully equipped kitchen {*including premium filtered water, plus Vitamix}, a relaxing living room with a day bed {*plus trundle}, and a bathroom with both a shower-filtered rain shower plus shower head along with {*the softest bamboo towels, &} a claw-foot bathtub. Immerse yourself in the amazing and tranquil surroundings of this phenomenal property. Rock on the front porch, while beholding wildlife all around. Barbecue out back on the private patio, while communing with multitudes of bird species. Or, stroll {*5 minutes} into town where plentiful epicurean options await you. Bask in Lake Michigan {*with her glorious beaches} just a few minutes walk or bike ride away. Revel in Ravinia concerts, then return home for after parties in our Lofty Movie Theater Perch & our Exalted-Space Grand Room, stocked up with Games, Glassware, Entertainment, & Ambience… Make your holiday one for the books with a stay at our eco-cottage sanctuary retreat home. Highland Park short term rental license:
RENT-006327-2024

Guest Reviews:

- "Thank you for this place! It was perfect for the 4 of us in the exact location that we wanted. My brother lives in highland park and we were less than a mile from his house. The house was spacious and had enough spaces for us to be together but apart when needed. We enjoyed the amenities the house provided also. The laundry was great since we were there for more than a couple of days. Great stay! "

Serene Home! 6 Bed&4.5 Bath w\/Kids den, Steam shower, Hot tub, Theatre, Bar..
House
Highland Park, Illinois, USA

Sunset Manor - A Serene and Cozy Haven

Welcome to Sunset Manor, an opulent retreat that defines contemporary elegance and comfort. This expansive 6-bedroom, 4.5-bathroom haven offers a harmonious blend of sophistication and relaxation.

As you step into Sunset Manor, a grand foyer welcomes you, setting the tone for the luxurious experience that awaits. The open-concept living spaces are adorned with stylish furnishings and abundant natural light, creating an inviting atmosphere for both relaxation and entertainment.

The heart of this residence is its gourmet kitchen, fully equipped with top-of-the-line appliances, making it a delight for both amateur and seasoned chefs. The adjacent dining area offers a perfect setting for intimate family meals or larger gatherings with friends.

Entertainment is taken to new heights with the dedicated theatre room, where cinematic experiences come alive. Sink into plush seating and enjoy movie nights or catch up on your favorite shows in a private, immersive setting. Right next door, the sleek bar area invites you to unwind and socialize with your favorite drinks.

Privacy is paramount in the six thoughtfully designed bedrooms, featuring plush bedding. Four and a half bathrooms showcase modern amenities for a spa-like experience.

Convenience is ensured with dedicated parking. Nestled in a serene location, Sunset Manor is ideal for family vacations, friend reunions, or corporate retreats. Book your stay for a synthesis of luxury, convenience, and tranquility. Your unforgettable escape begins here.

Amenities:

Fireplace/Heating • Kitchen • Pet Friendly • Other • Bedding/Linens • Air Conditioner • Security/Safety • Hot Tub • Parking • Tv • Sports/Activities • Child Friendly

Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits
House
Highland Park, Illinois, USA

Welcome to Sunset Manor, a luxurious 6-bedroom, 4.5-bathroom residence where elegance and comfort come together to create unforgettable memories. Located in the prestigious Northshore neighborhood of Highland Park, this sophisticated retreat is perfect for families or groups, offering modern amenities, stylish details, and a peaceful escape. Relax in the hot tub, entertain in the beautifully designed spaces, or explore nearby landmarks, including the iconic gates of Michael Jordan’s neighborhood estate. Sunset Manor is the perfect backdrop for your next getaway.

The chic design and extensive amenities are sure to impress.

★ HIGHLIGHTS ★

✔ 6 Cozy Bedrooms

✔ Multiple Living Areas

✔ Play room for Kids

✔ Full Kitchen & Dining Area

✔ Full Bar Area

✔ Theater room & Game area

✔ Hot Tub

✔ High speed Wi-Fi

✔ Free Driveway parking

✔ Pack-N-Play & Highchair Provided

The Space:

Welcome to your dream vacation rental! This exceptional home offers the ultimate blend of relaxation and entertainment, making it the perfect choice for families and groups.

Spacious Living Room: As you enter, you’ll be greeted by a beautifully designed living room featuring high ceilings, a contemporary art wall, and a large TV. It’s the perfect space to unwind and feel at home.

Family-Friendly Kitchen and Dining: On the same level, enjoy a modern, fully-equipped kitchen with a cozy breakfast nook and an adjacent dining room—ideal for family meals and gatherings.

Fun Playroom for Kids: Our home is perfect for families, with a dedicated playroom designed to entertain younger children. It includes an indoor play set, pretend kitchen, TV, and comfy furniture, ensuring hours of fun and engagement.

Bar & Entertainment Area: Just a few steps up, you’ll find a sophisticated full bar area complete with plush seating and a foosball table. It’s the ultimate space for adults to relax, enjoy drinks, and have lively conversations. We have a TV at bar area to watch sports.

Home Theater and Game Room: Descend to the basement where a luxurious theater room awaits. Enjoy your favorite movies on a cozy sectional, and challenge friends to a game of pool. For fitness enthusiasts, there’s also workout equipment available.

Perfect for Relaxation and Fun: This home is designed with comfort and entertainment in mind, making it an ideal choice for a memorable family vacation, a group getaway, or a relaxing retreat. Book now to enjoy a stay in this top-rated vacation rental!

Stunning Kitchen & Elegant Dining Areas: Perfect for Culinary Creations and Entertaining
This beautifully decorated kitchen is the heart of the home, featuring spacious countertops, ample cabinetry, and modern appliances that make cooking both easy and enjoyable. The breakfast nook and dining table offer plenty of seating for the whole family. Enjoy the convenience of a local coffee station, perfect for savoring the best brews.

✔ Eat at the Kitchen with breakfast nook

✔ Coffee Machine

✔ Hot water Kettle, Microwave, Toaster & Blender

✔ Stainless Steel Appliances

✔ Dining room with Seating for 8

✔ Cooking & Dining Essentials


Tranquil Bedrooms & Serene Bathrooms: Your Private Retreat Awaits

♛ Bedroom 1 (Master Bedroom)

✔ King Size Bed with Nightstands

✔ Memory Foam Mattress

✔ Accent Chairs to Relax

✔ Closets for Storage

✔ Standing Mirror


♛ Bedroom 2

✔Queen Size Bed with Nightstands

✔ Closet for Storage


♛ Bedroom 3

✔ 2 Bunk beds (Sleeps 4) with a Nightstand

✔ Closet for Storage


♛ Bedroom 4

✔ Twin Size Beds (Two) with Nightstands

✔ Closets for Storage


♛ Bedroom 5

✔ Full Bed with Night stand

✔ Closet


♛ Bedroom 6

✔ Full Bed with Night stand

✔ Closet



🛏Additional Sleeping

✔ Pack-N-Play Provided


Master Bathroom

✔ Stand Up Shower

✔ Soak in Tub

✔ Toilet & Floating Double Vanity

✔ Soap & Shampoo


Bathroom 2

✔ Shower Tub

✔ Toilet & Vanity

✔ Soap & Shampoo


Bathroom 3

✔ Stand Up Shower

✔ Toilet & Floating Vanity

✔ Soap & Shampoo


Bathroom 4

✔ Stand Up Shower & Steam

✔ Toilet & Floating Vanity

✔ Soap & Shampoo


Powder Room

✔ Toilet & Floating Vanity


IDEAL FOR FAMILIES

✔ Quiet Neighborhood

✔ Large Yard

✔ Pack-N-Play

✔ Highchair

✔ Games for Kids & Reading Material


Prime Location with Exceptional Connectivity

Nestled in a highly walkable neighborhood, this property is adjacent to Sleepy Hollow Park, offering scenic walking paths. Just minutes away is Danny Cunniff Park, featuring a range of sports and recreational activities, including the Centennial Ice Arena. The Fort Sheridan Metra Station, a quick 6-minute drive, ensures easy access to downtown Chicago and beyond. Additionally, enjoy convenient drives to Naval Station Great Lakes (19 minutes), Ravinia Festival (16 minutes), Chicago Botanic Garden (11 minutes), and Rosewood Beach (13 minutes).

(distances in time are calculated considering travel by car)


Guest Access:

Guests have access to the entire home, with the exception of a locked supply closet & storage room.

Other things to note:
No events or parties are allowed.
Sometimes we might require a security deposit and/or proof of ID to validate the guest name and age to protect both host & the guest.

Amenities:

Balcony/Terrace • Sports/Activities • Pet Friendly • Other • Kitchen • Tv • Hot Tub • Child Friendly • Security/Safety • Fireplace/Heating • Bedding/Linens • Laundry

Safe and Secure, Charming, Clean Studio
Apartment
Highland Park, Illinois, USA

Our studio apartment is in a secure building, centrally-located in the walkable Rivinia Business District of Highland Park.

Very quiet building, 2nd floor apartment with no neighbors above or below.

Amenities include: shared laundry, stocked kitchen (no dishwasher), and free overnight lot parking (must provide license plate number)

Just 3 blocks to the Rivinia Metra stop, less than a one-mile walk to the Michigan lakefront and 2 miles from Chicago Botanic Gardens. Walgreens is across the street!

Centrally located between many public and private golf courses.

Amenities:

Bedding/Linens • Fireplace/Heating • Security/Safety • Wellness Facilities • Other • Guest Services • Internet • Parking • Kitchen • Laundry

Charming 2-bedroom apartment in delightful Highwood 2 minutes to Train station!
Apartment
Highwood, Illinois, USA

You will be close to everything when you stay at this centrally located 2nd floor apartment. Walking distance to Highwood train station and only a 45 minute train ride to Downtown Chicago.
Sleeps 7. Apartment Features:

Bedroom 1- Queen Bed
Bedroom 2- Twin XL/Queen Bunk Bed
Living Room - Queen Pull Out Sofa Sleeper
Workspace with Desk
Fully Equipped Kitchen
YouTube TV
Keurig Coffee Maker w/ K Cups
High Speed Internet
Parking for 2 Cars
AC units for all rooms
$10 pet fee per pet, per night

Located in Highwood, half way between Chicago and Milwaukee. Just a 35 minute train ride to downtown Chicago on the express train, Close to Six Flags, Great Lakes Navy Base, Lake Michigan beaches, forest preserves, train station and the Chain of Lakes!

This Apartment is located on the 2nd floor, stairs required to access the unit.

Amenities:

Pet Friendly • Security/Safety • Child Friendly • Internet • Fireplace/Heating • Wellness Facilities • Other • Air Conditioner • Bedding/Linens • Laundry

Clean, Quiet, Secure, with Beautiful Park Views - 1 bedroom plus den in Rivinia
Apartment
Highland Park, Illinois, USA

Our 1 bedroom + den apartment is peaceful & stylish for your monthly living needs.

Centrally-located 2 blocks from UP-N Metra, the apartment includes: stocked kitchen (no dishwasher), free shared laundry, free overnight parking (must provide license plate), and private sleeping on a king-bed with adjustable base. An additional twin bed may be added for guests (added fee).

10 min from Chicago Botanic Garden, easy walk to Lake Michigan and Rivinia Farmer’s Market. Walgreens across the street.

Amenities:

Security/Safety • Laundry • Bedding/Linens • Internet • Air Conditioner • Child Friendly • Wellness Facilities • Fireplace/Heating

Cozy 2 bed Apt- 2 train stops to the Naval Base!
Apartment
Highwood, Illinois, USA

Your family will be close to everything when you stay at this centrally located apartment in downtown Highwood. Walking distance to train station and only 2 stops to the Great Lakes Naval Base!
Sleeps up to 7. Apartment Features:

Bedroom 1- Queen Bed
Bedroom 2- Twin XL/Queen Bunk Bed
Living Room - Queen Pull Out Sofa Sleeper
Fully Equipped Kitchen
YouTube TV
Keurig Coffee Maker w/ K Cups
High Speed Internet
Parking for 2 Cars
AC units for all rooms

This Apartment is located on the 2nd floor, 1 stair case to enter apartment.

Quaint, little apartment located in Highwood, half way between Chicago and Milwaukee. Just a 35 minute train ride to downtown Chicago on the express train, Close to Six Flags, Great Lakes Navy Base, Lake Michigan beaches, forest preserves, train station and the Chain of Lakes.

20 Minute Drive to Great Lakes Naval Base!
$25 Pet fee per pet, per night

24-hour outdoor camera and remote security team monitoring not actively monitored
Noise detection sensors installed in property – These devices monitor decibel levels inside the property 24 hours a day and automatically notify us if noise levels are too high.

Amenities:

Entertainment • Kitchen • Fireplace/Heating • Other • Laundry • Child Friendly • Sports/Activities • Security/Safety • Tv • Air Conditioner • Bedding/Linens • Pet Friendly

Hidden Gem Cottage alongside Park, by Beach, Train, Ravinia, Botanic Garden
House
Glencoe, Illinois, USA

Unique Hidden Gem Cottage, alongside beautiful green park, famous Green Bay Trail, Ravinia and Botanic Gardens, Few blocks from the beach & Metra train to Chicago. Relax in our historic cottage and gardens. Peaceful yet central, vintage yet modern, mid century charm.
Open layout, chef’s kitchen and stylish family room. Fully stocked kitchen. Two private bedrooms, two updated bathrooms, new laundry.
Enjoy the garden alongside the beautiful park settings.

Amenities:

Fireplace/Heating • Laundry • Wellness Facilities • Balcony/Terrace • Child Friendly • Security/Safety • Bedding/Linens • Kitchen • Air Conditioner • Other • Internet

Highland Park Family Ranch - Walk to Lake & Metra to Chicago!
House
Highland Park, Illinois, USA

Your Highland Park Retreat Awaits!

Nestled in the peaceful and walkable Chicago's North Shore neighborhood of Highland Park, our sophisticated ranch-style home offers the perfect blend of tranquility and convenience. Imagine strolling to local dining, exploring scenic trails to Lake Michigan, or hopping on the Metra for a quick trip to downtown Chicago – all just moments away!

Step inside and discover a haven of comfort and style. Recently renovated, our home features tasteful décor, comfortable furnishings, and modern amenities designed for a relaxing and memorable stay.

Highlights You'll Love:

Perfect for Families & Groups: Sleeps up to 10 with 4 cozy bedrooms (including a king-bed master), 5 beds, and 3 full bathrooms plus 2 comfortable futons.

Two Living Areas: Enjoy ample space to relax with 2 living rooms, both equipped with 55" Smart TVs (Netflix, Prime, etc.) and comfortable seating. One even features a cozy electric fireplace.

Entertainment for Everyone: From board games and puzzles to a fun game area with table tennis, air hockey, and indoor basketball, there's something for all ages.

Open & Social Kitchen: Prepare delicious meals in our fully stocked, open-concept kitchen with stainless steel appliances, a wine chiller, and both a breakfast nook (seats 4) and a dining table (seats 6). Enjoy our local coffee station!

Modern Comforts: Stay connected with high-speed Wi-Fi, enjoy the convenience of free driveway parking, and travel light with our provided pack-n-play and highchair.

Outdoor Relaxation: Savor your morning coffee or evening cocktails on the private patio and enjoy the large yard.

Sleeping Arrangements:

Bedroom 1 (Master): King-size bed, memory foam mattress, ample closet space.

Bedroom 2: Queen-size bed, dedicated workspace (desk & chair).

Bedroom 3: Double-size bed.

Bedroom 4: Two twin-size beds.

Additional Sleeping: 2 comfortable futons.

Location, Location, Location!

Our Highland Park home offers unparalleled access to the best the North Shore and Chicago have to offer:

Walkable Neighborhood: Enjoy strolling to local restaurants and shops.

Outdoor Adventures: Steps from Fort Sheridan Trails leading to the beautiful shores of Lake Michigan.

Dining & Entertainment: A short drive to vibrant Highwood Downtown with its excellent dining and entertainment options.

Easy City Access: The Metra station is just a block away, providing convenient transportation to downtown Chicago and surrounding areas.

Nearby Attractions:

15 minutes to Naval Station Great Lakes

14 minutes to the renowned Ravinia Festival

11 minutes to the stunning Chicago Botanic Garden

13 minutes to the beautiful Rosewood Beach

Guest Access:
Guests have full access to the entire home, excluding a locked supply closet and storage room.

Other things to note:
No events or parties are allowed.
Sometimes we might require a security deposit and/or proof of ID to validate the guest name and age to protect both host & the guest.

Amenities:

Laundry • Fireplace/Heating • Bedding/Linens • Child Friendly • Security/Safety • Air Conditioner • Parking • Internet • Sports/Activities • Tv • Pet Friendly • Kitchen

Cozy Highland Park Home
House
Highland Park, Illinois, USA

Step into the embrace of comfort and tranquility at our newly renovated haven nestled in the heart of Highland Park! With 4 bedrooms and 4 bathrooms, our spacious retreat offers ample room for up to 10 guests to unwind in style. Immerse yourself in the charm of downtown Highland Park, mere moments away, where a vibrant tapestry of shops, eateries, and attractions awaits your exploration. Whether it's a cherished family retreat or a memorable gathering with friends, our home beckons with open arms, promising an unforgettable stay filled with laughter, relaxation, and cherished moments

Amenities:

Child Friendly • Bedding/Linens • Parking • Pet Friendly • Air Conditioner • Kitchen • Fireplace/Heating • Smoking • Other • Laundry • Internet • Wellness Facilities

Modern Retreat at Highland Park
House
Highland Park, Illinois, USA

Welcome to our sophisticated ranch-style home, nestled in the serene Chicago’s north shore neighborhood of Highland Park. This carefully curated residence offers a peaceful retreat in a walkable neighborhood with convenient access to dining, Trails to Lake Michigan, Metra to downtown Chicago and many more.
Step inside and discover an oasis of elegance and comfort. The interior boasts tasteful decor, comfortable furnishings, and modern amenities, creating a haven of relaxation and style. Whether you're savoring a cup of coffee on the private patio or venturing out to explore the area, this home provides the perfect backdrop for a memorable vacation experience.

ABOUT THE SPACE
★ HIGHLIGHTS ★
✔ 4 Cozy Bedrooms: 5 Beds, 3 Full Bathrooms plus 2 Fultons
✔ 2 Living rooms with TV’s
✔ Renovated space
✔ Open concept Living area, Stocked Kitchen & Dining
✔ High speed Wi-Fi
✔ Free Driveway parking
✔ Pack-N-Play & Highchair Provided

ENTERTAINING LIVING ROOM
Relax and watch your favorite show or movie with our 55° Smart TV, laugh and compete with our collection of board games, challenge each other with a puzzle, take a moment to browse our books and magazines, but most importantly, create everlasting memories with your friends and family in this beautiful home.
✔ 55 inch Smart TV - Includes apps like Netflix, Prime, etc in Living room & Family room
✔ Cozy Fulton, Sofas & Lounge Chairs in Living & Family room with electric fireplace
✔ Coffee Table
✔ Office Desk
✔ Games, Reading Material
✔ Game area with Table Tennis, Air Hockey, Indoor Basketball

STOCKED KITCHEN & DINING
Spacious countertops, ample cabinetry, and modern cooking appliances make for an easy and creative time in the center of this home. There is plenty of seating for the whole family featured at the breakfast nook and the dining table. Take advantage of the local coffee station, boasting the best brews. Enjoy your favorite wine served chilled using a wine chiller.
✔ Eat at the Kitchen Island, seating for 4
✔ Coffee Machine
✔ Hot water Kettle, Microwave, Toaster & Blender
✔ Wine Chiller
✔ Stainless Steel Appliances
✔ Dining Table with Seating for 6
✔ Cooking & Dining Essentials

RELAXING BEDROOMS & BATHROOMS
🛏Bedroom 1 (Master Bedroom)
✔ King Size Bed with Nightstands
✔ Memory Foam Mattress
✔ Closets for Storage
✔ Standing Mirror

🛏Bedroom 2
✔Queen Size Bed with Nightstands
✔ Office Desk & Chair
✔ Closet for Storage

🛏Bedroom 3
✔ Queen Size Bed with Nightstands
✔ Closet for Storage

🛏Bedroom 4
✔ Twin Size Beds (Two) with Nightstands
✔ Closets for Storage

🛏Additional Sleeping
✔ Two Futons in Living Room
✔ Pack-N-Play Provided

🛁Master Bathroom
✔ Stand Up Shower
✔ Toilet & Floating Vanity
✔ Soap & Shampoo

🛁Bathroom 2
✔ Shower Tub
✔ Toilet & Floating Vanity
✔ Soap & Shampoo

🛁Bathroom 3
✔ Stand Up Shower
✔ Toilet & Vanity
✔ Soap & Shampoo

IDEAL FOR FAMILIES
✔ Quiet Neighborhood
✔ Large Yard
✔Pack-N-Play
✔Highchair
✔Games for Kids & Reading Material

ABOUT AREA
Neighborhood is highly walk friendly with Fort Sheridan Trails leading to Lake Michigan. Few minutes away from Highwood Downtown with Great Places to Eat & Entertain. Metra Station a Block away which goes to Downtown Chicago and Surrounding Areas with great Connectivity. 15 Minutes drive to Naval Station Great Lakes. 14 Minutes drive to Ravinia Festival. 11 Minutes drive to Chicago Botanic Garden. 13 Minutes drive to Rosewood Beach.

Guest Access
Guests have access to the entire home, with the exception of a locked supply closet & storage room.

Amenities:

Sports/Activities • Internet • Fireplace/Heating • Pet Friendly • Parking • Tv • Other • Laundry • Air Conditioner • Balcony/Terrace • Security/Safety • Bedding/Linens

Highland Park Vacation-Rentals on the Map

Compare the Best Vacation-Rentals in Highland Park – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
2-Acre Highland Park Retreat with Heated Pool ~ 5* 2707 Mavor Lane, Highland Park, IL, IL 60035, USA 648 4.0 9.8 9 Click here
Courtyard by Marriott Chicago Highland Park/Northbrook 1505 Lake Cook Road, Highland Park, IL, 60035, USA 118 3.0 9.0 1000 Click here
Luxury Suite at Private Beach North Shore Residence 110 Lakewood Place, IL, IL 60035, USA 152 4.0 9.3 3 Click here
Courtyard by Marriott Chicago Deerfield 800 Lake Cook Rd, Deerfield, IL, 60015, USA 108 3.0 8.4 926 Click here
Super 8 by Wyndham Deerfield - Northbrook 340 South Waukegan Road, Deerfield, IL, IL 60015, USA 246 3.0 7.1 304 Click here
Residence Inn By Marriott Chicago Deerfield 530 Lake Cook Rd, Deerfield, IL, 60015, USA 168 3.0 9.0 487 Click here
Courtyard Chicago Highland Park/Northbrook 1505 Lake Cook Road, Highland Park, IL, IL 60035, USA 158 3.0 8.3 153 Click here
Super 8 by Wyndham Deerfield/Northbrook 340 South Waukegan Road, Deerfield, IL, 60062, USA 72 2.0 7.6 1006 Click here
Courtyard Chicago Deerfield 800 Lake Cook Road, Deerfield, IL, IL 60015, USA 122 3.0 7.8 91 Click here
Stunning & Stylish Downtown Studio - Highland Park Highland Park, Illinois, USA 157 2.0 8.8 6 Click here
Residence Inn Chicago Deerfield 530 Lake Cook Road, Deerfield, IL, IL 60015, USA 179 3.0 8.4 79 Click here
The Sunset Manor - Luxe Mansion for Serene retreat Highland Park, Illinois, USA 959 2.0 9.0 2 Click here
Modern Luxe Home w/Gameroom and Electric Fireplace Highland Park, Illinois, USA 999 2.0 6.0 2 Click here
Serene Retreat Awaits You! Highland Park, Illinois, USA 447 9.6 49 Click here
Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan Highland Park, Illinois, USA 286 10.0 24 Click here
Chic Studio - In Downtown Highland Park, by Metra Highland Park, Illinois, USA 137 8.4 16 Click here
Modern Luxe home w\/Gameroom and Electric Fireplace Highland Park, Illinois, USA 612 8.4 6 Click here
Chic Studio in Downtown Highland Park near Metra Highland Park, Illinois, USA 151 8.0 4 Click here
Near Ravinia and Navy Base, charming 3-bedroom house in peaceful Highland Park Highland Park, Illinois, USA 519 10.0 4 Click here
Condo - Downtown Highland Park Highland Park, Illinois, USA 125 5.0 2 Click here
Safe & Secure Parkview-Sleep Sanctuary+Kitchen Highland Park, Illinois, USA 115 10.0 1 Click here
Cute Ranch House close to town monthly stay Deerfield, Illinois, USA 140 6.0 1 Click here
Picturesque! Mid Mod Home - 20min from Chicago! Highland Park, Illinois, USA 278 10.0 1 Click here
Entire home, close to Ravinia Festival, Lake, Town, and Train to the city. Highland Park, Illinois, USA 524 10.0 1 Click here
Serene Home! 6 Bed&4.5 Bath w\/Kids den, Steam shower, Hot tub, Theatre, Bar.. Highland Park, Illinois, USA 683 10.0 1 Click here
Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits Highland Park, Illinois, USA 776 10.0 1 Click here
Safe and Secure, Charming, Clean Studio Highland Park, Illinois, USA 110 1 Click here
Charming 2-bedroom apartment in delightful Highwood 2 minutes to Train station! Highwood, Illinois, USA 121 1 Click here
Clean, Quiet, Secure, with Beautiful Park Views - 1 bedroom plus den in Rivinia Highland Park, Illinois, USA 128 1 Click here
Cozy 2 bed Apt- 2 train stops to the Naval Base! Highwood, Illinois, USA 186 1 Click here
Hidden Gem Cottage alongside Park, by Beach, Train, Ravinia, Botanic Garden Glencoe, Illinois, USA 225 1 Click here
Highland Park Family Ranch - Walk to Lake & Metra to Chicago! Highland Park, Illinois, USA 543 1 Click here
Cozy Highland Park Home Highland Park, Illinois, USA 563 1 Click here
Modern Retreat at Highland Park Highland Park, Illinois, USA 595 1 Click here

Note: The prices for each Vacation-Rentals in Highland Park do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Vacation rentals in Highland Park that include a pool include:

  • 2-Acre Highland Park Retreat with Heated Pool ~ 5*.- Review Count: 9, Rating: 9.8
  • Courtyard by Marriott Chicago Highland Park/Northbrook.- Review Count: 1000, Rating: 9.0
  • Courtyard by Marriott Chicago Deerfield.- Review Count: 926, Rating: 8.4

Vacation rentals in Highland Park offering shuttle or transport options include:

  • Courtyard Chicago Deerfield.- Review Count: 91, Rating: 7.8
  • Residence Inn Chicago Deerfield.- Review Count: 79, Rating: 8.4

These vacation rentals in Highland Park provide spa or wellness access:

  • Picturesque! Mid Mod Home - 20min from Chicago!.- Review Count: 1, Rating: 10.0
  • Serene Home! 6 Bed&4.5 Bath w\/Kids den, Steam shower, Hot tub, Theatre, Bar...- Review Count: 1, Rating: 10.0

Family-friendly vacation rentals in Highland Park include:

  • 2-Acre Highland Park Retreat with Heated Pool ~ 5*.- Review Count: 9, Rating: 9.8
  • Courtyard by Marriott Chicago Highland Park/Northbrook.- Review Count: 1000, Rating: 9.0
  • Luxury Suite at Private Beach North Shore Residence.- Review Count: 3, Rating: 9.3

Pet-friendly vacation rentals in Highland Park include:

  • Super 8 by Wyndham Deerfield - Northbrook.- Review Count: 304, Rating: 7.1
  • Residence Inn Chicago Deerfield.- Review Count: 79, Rating: 8.4
  • The Sunset Manor - Luxe Mansion for Serene retreat.- Review Count: 2, Rating: 9.0

Vacation rentals in Highland Park that include breakfast options include:

  • Courtyard by Marriott Chicago Highland Park/Northbrook.- Review Count: 1000, Rating: 9.0
  • Courtyard by Marriott Chicago Deerfield.- Review Count: 926, Rating: 8.4
  • Residence Inn By Marriott Chicago Deerfield.- Review Count: 487, Rating: 9.0

Vacation rentals in Highland Park with private or on-site parking include:

  • 2-Acre Highland Park Retreat with Heated Pool ~ 5*.- Review Count: 9, Rating: 9.8
  • Courtyard by Marriott Chicago Highland Park/Northbrook.- Review Count: 1000, Rating: 9.0
  • Luxury Suite at Private Beach North Shore Residence.- Review Count: 3, Rating: 9.3

Some of the best Vacation Rentals in Highland Park are:

  • 2-Acre Highland Park Retreat with Heated Pool ~ 5*.- Review Count: 9, Rating: 9.8
  • Luxury Suite at Private Beach North Shore Residence.- Review Count: 3, Rating: 9.3
  • Courtyard by Marriott Chicago Highland Park/Northbrook.- Review Count: 1000, Rating: 9.0

Some of the popular Vacation Rentals in Highland Park are:

  • Super 8 by Wyndham Deerfield/Northbrook.- Review Count: 1006, Rating: 7.6
  • Courtyard by Marriott Chicago Highland Park/Northbrook.- Review Count: 1000, Rating: 9.0
  • Courtyard by Marriott Chicago Deerfield.- Review Count: 926, Rating: 8.4