Best Apartments in Old Saybrook

Top Apartment Rentals in Old Saybrook

Find your ideal city escape with our handpicked apartment selections in Old Saybrook, designed for those seeking both comfort and style during their stay.

Apartments in Old Saybrook
The Millhouse Downtown Chester
Apartment
5 West Main Street, Chester, CT, CT 06412, USA

17 miles from Wesleyan University in Chester, The Millhouse Downtown Chester offers accommodations with access to beauty services. The air-conditioned accommodation is 5 miles from Goodspeed Opera House. There's an outdoor fireplace and guests can use free Wifi and free private parking. Offering a patio with river views, this apartment also features a flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a bath and a hair dryer. The apartment offers bed linen, towels, and laundry service. Guests can make the most of the warm weather with the property's barbecue facilities. Guests at the apartment will be able to enjoy activities in and around Chester, like walking tours and pub crawls. Guests at The Millhouse Downtown Chester can enjoy canoeing and hiking nearby, or make the most of the garden. Central Connecitcut State University is 31 miles from the accommodation, while Thimble Islands is 31 miles from the property. Tweed-New Haven Airport is 34 miles away.

Amenities:

Breakfast • Bar • Air Conditioner • Fireplace/Heating • Guest Services • Ocean View • Wellness Facilities • Oceanfront • Parking • View • Other • Security/Safety

Apartments in Old Saybrook
Renovated 1 bedroom Cozy Apt-Madison
Apartment
Madison, Connecticut, USA

Fully renovated 1 bed , 1 bath, 650 APARTMENT. Walk to surf club beach in Madison and bike to town center. This is a 2nd floor unit with tons of light. Comes with all the comforts like linens, Keurig, glass shower, tasteful furniture, WIFI, Cable etc. Apartment is located in a carriage house on a 1.2 acres estate property. There is a washer /dryer in the foyer of carriage house to use. There is a private deck off the kitchen to enjoy table and chairs with a sitting area. The stone patio below on ground level has a grill and table and chairs to enjoy. All utilities are included for extended stay. There are 2 bikes for renters to use. We are also a stones throw from Madison golf course, Madison Beach Hotel, Town Green and downtown shopping is a walk or bike away. This Unit is 2nd floor with two entrances, one with a keypad. There is a parking lot area for carriage house and this unit has up to two spaces.

in summer. Prefer a one month minimum but would consider 2 week duration.

Guest Reviews:

- "Beyond my family’s expectations. Renovated unit including new furniture, towels and linens, plus an outdoor gas grill and bicycles. The location is within walking or biking distance of the beach (down a private lane adjacent to the carriage house), town and Madison Beach Hotel. We walked a couple times to the Madison Beach Hotel to have drinks, dinner and watch the evening sunset – very relaxing. Madison is the quintessential New England town with a variety of restaurants and stores to keep you busy. Finally, I can’t say enough about the hosts. Great people who were friendly, accommodating and made my family feel right at home. I wouldn’t hesitate to recommend a stay at this unit."

Apartments in Old Saybrook
Cozy apartment, private beach & jacuzzi
Apartment
89 Old Kelsey Point Road, Westbrook, CT, CT 06498, USA

28 miles from Wesleyan University in Westbrook, Cozy apartment, private beach & jacuzzi features accommodations with access to a hot tub. 18 miles from Goodspeed Opera House and 25 miles from Thimble Islands, the apartment provides a private beach area. The apartment also offers free Wifi and free private parking. The air-conditioned apartment consists of 1 bedroom, a living room, a fully equipped kitchenette with a microwave and a coffee machine, and 1 bathroom with a hot tub and bathrobes. Guests can take in the ambience of the surroundings from an outdoor dining area. For added privacy, the accommodation features a private entrance. City Hall is 29 miles from the apartment, while Yale University is 29 miles from the property. Tweed-New Haven Airport is 27 miles away.

Guest Reviews:

- "Fantastic !!" - "Definitely check out" - "Practical, clean, and convenient place for a small group (2-4) of people to stay."

Apartments in Old Saybrook
Cozy apartment with a bird's eye view of Chester. 5 minute walk downtown
Apartment
Chester, Connecticut, USA

Step back in time in this cozy third floor apartment with private entrance. Here you will enjoy a bird's eye view of Chester Center from the peace and privacy of this 1889 Queen Anne Victorian. Situated in a tranquil, park like setting on two acres, this gingerbread apartment can accommodate up to 4 guests (including children over 2 years old). There are three flights of stairs, two exterior and one interior to access the apartment. Chester center is an easy five minute walk from the apartment where you can find an artisan ice cream shop, an inviting brew pub, fabulous restaurants, interesting shops and a farmers market on Sundays in the summer. The CT shore is a 15 minute drive and we are surrounded by hiking and boating opportunities as well as tourist attractions like Gillette Castle, the Essex Steam Train and the Goodspeed Theaters. This property is owner occupied on the first two floors. If you are looking for a laid back, clean and comfortable place to stay, look no further.

Guest Reviews:

- "Just as advertised" - "We enjoyed our stay and our visit to the area my relatives lived in the early 1900’s. The accommodations were very nice." - "First Friday in December is a great way to start the season!"

Apartments in Old Saybrook
Walk To Goodspeed Opera House from this quaint 2 BDRM APT
Apartment
2 Norwich Road Rear, East Haddam, CT, CT 06423, USA

Walk To Goodspeed Opera House from this quaint 2 BDRM APT offers accommodations in East Haddam, 28 miles from Eastern Connecticut State University. With free private parking, the property is a 2-minute walk from Goodspeed Opera House and 17 miles from Wesleyan University. This air-conditioned 2-bedroom apartment comes with a dining area, a cable flat-screen TV, and a fully equipped kitchen with a dishwasher. Towels and bed linen are provided in the apartment. For added privacy, the accommodation features a private entrance. The nearest airport is Tweed-New Haven Airport, 37 miles from the apartment.

Guest Reviews:

- "Met our needs" - "Cute and convenient overnight stay" - "The apartment was very comfortable and in a great location. We would stay again." - "Adequate for a basement apartment under an ice cream shop. Overpriced for what you get."

Apartments in Old Saybrook
The little Chestnut. A charming historic apartment in Downtown Chester
Apartment
Chester, Connecticut, USA

Last-minute bookings, please message us and we may also be able to accomodate one-night stays. Located in the village of Chester, this delightful apartment, located above a charming bookstore, features 2 cozy bedrooms - one with a queen bed (primary bedroom on the third floor) and the other with a Trundle bed, located on the second floor. With amenities like heating, AC, WiFi, and a washing machine, guests can enjoy a comfortable stay. It has a full bathroom with a shower on the third floor next to the primary bedroom. From the front door you will enter into a mud room and stairs that will take you to the second floor where the living room, dining room, kitchen and Trundle bedroom are located. An other flight of stairs will take you to the third floor where the Primary bedroom and bathroom are located. This little hideaway is buffered by the village parking lot and a brook offering in-village convenience with natural serenity. The main strip of Chester is just seconds away, (walking distance), to excellent restaurants, boutique shops and art galleries. The grounds are filled with floral planters and there is a wonderful little park across the brook with picnic table and gazebo for your enjoyment.

Guest Reviews:

- "This property was such a nice place to stay! Its right above a little romantic bookshop which is a little added bonus. It is within walking distance of several boutiques, delcious restaurants, and a local brewery. Multiple hiking spots within short driving distance. The owner was also very helpful and kind. Loved our little getaway! " - "Can't say enough about the whole experience with this problem. The owner was super nice, walked me through the entry process. Was very responsive when I had questions about the property and local items. The Little Chestnut in Chester is an excellent jumping off spot for a lot of activities around the lower Connecticut River area. The town of Chester has a really nice vibe and could spend all the time there. The Little Chestnut is set up for about 4 people. The beds were super comfortable, and had extra blankets for this cool nights. The heater worked great and kept the cabin very warm. The electric fireplace was also very warm and gave an awesome atmosphere without the hassle of an actual fireplace. Hot water heater was plenty big for 3 adults to take a shower and not run out of hot water. The kitchen was fully stocked with cooking and eating utensils, however with so many great eating places we didn't do any cooking. When we stayed the little bookstore below was open and was a fun visit for the girls. If we could give more stars I certainly would. "

Apartments in Old Saybrook
Quiet Killingworth Rental with Deck and Grill!
Apartment
Deep River, CT, USA

Quiet Killingworth Rental with Deck and Grill! offers accommodations in Deep River, 15 miles from Wesleyan University and 23 miles from Thimble Islands. The property is around 25 miles from Yale University, 25 miles from City Hall, and 27 miles from The Yale Bowl. Free Wifi is available throughout the property and Goodspeed Opera House is 12 miles away. The air-conditioned apartment consists of 1 bedroom, a living room, a fully equipped kitchen with an oven and a coffee machine, and 1 bathroom with a bath and a hair dryer. Towels and bed linen are provided in the apartment. For added privacy, the accommodation features a private entrance. Central Connecitcut State University is 29 miles from the apartment. Tweed-New Haven Airport is 25 miles away.

Amenities:

Sports/Activities • Internet • Child Friendly • Other • Security/Safety • Fireplace/Heating • Parking

Apartments in Old Saybrook
Newly Renovated Guest Suite - Steps to West Beach!
Apartment
Westbrook, Connecticut, USA

Escape to the charming coastal town of Westbrook, CT and experience ultimate luxury & comfort in your own private guest suite!

Completely renovated in 2022 with modern amenities, lighting, heating/cooling, and more!

Guest Reviews:

- "Location is clean and is a great proximity to beach and town. Perfect size for a weekend getaway " - "My stay was perfect. I needed a place near the shoreline to visit family/ friends that was also quiet and had amenities such as a kitchenette. It was perfect for relaxing and resting after having a joint replacement surgery. I can say enough, it was only a few blocks from the local beach. It’s my stomping grounds from living in Ct so it really was a delight to be in such an immaculate place. I will be back !!!"

Apartments in Old Saybrook
Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town
Apartment
Madison, Connecticut, USA

Birdsong is a handicap accessible apartment, which is attached to the west side of our house with beautiful views of the sunsets. We have 2 acres of land with lush gardens and a waterfall and lily pond. The cathedral ceiling apartment, with plenty of natural light, has an open floor plan of a living room, dining area and kitchen with a separate bedroom. The bedroom has a queen size bed with California closets, while the bathroom has a handicap accessible shower and sink. In the kitchen you will find everything you will need to create your own favorite meals. Have breakfast, lunch or dinner on the terrace in this tranquil setting, while listening to the waterfall of the pond. A gas grill is available for use.

The town of Madison, which is located on Long Island Sound, is a perfect destination for relaxing an exploring. Centrally located - New York City is 2 hours away while Boston is 2 ½ and New Haven twenty minutes. The train from the downtown station will connect you with all of these destinations, but why leave the quaint town of Madison. Stroll through the town center and you will find an Cinema, the renowned RJ Julia ‘s independent bookstore, coffee shops, a cheese shop, International and American restaurants, boutiques, a library, outdoor sculpture by nationally renowned artists and a large grocery store.
Joining us for the summer? As is typical of New England towns, there is a green in town, where you will find concerts, a farmer’s market, arts and crafts fairs and antique shows from May through September. On the 4th of July weekend, join the local fun watching the parade, relaxing at the Pops summer concert and watching the fireworks.
Madison’s beaches, as well as, Hammonasset State Park (beach), have playgrounds, tables and grills for picnicking, sports fields and bocce/pétanque courts. (We will provide the pétanque balls.)
There are trails throughout town where you can hike and a nature center for birding and learning about the local animals.
There are a myriad of things to do for those cool or rainy days. You might decide to follow the Impressionist or the wine trial throughout Connecticut, or you might visit one of the many museums, go shopping (there are 2 Outlet Centers within a 20 minute drive), go to the theater, listen to live music or visit one of the gambling casinos.

Guest Reviews:

- "Great scenery all around. Peaceful place to stay yet close enough to everything you need for a fun trip to the coast of CT." - "The accommodations at Birdsong were spacious, comfortable & exceptionally clean! We were greeted by our hosts Kathleen & Dean, who gave us a tour & showed us everything we needed to know to make our stay as smooth as possible. We had delicious scones, wine, & beautiful flowers upon our arrival - we enjoyed the outdoor patio with the humming birds & lovely flowering landscape. Beach chairs , towels, umbrella & beach pass were available for us to use during our stay - there were lots of great restaurants nearby. Kathleen & Dean responded quickly to any questions we had throughout our weekend. It was so quiet & relaxing. We are looking forward to staying at Birdsong again soon! Trish & Bill"

Apartments in Old Saybrook
Convenient and cute in Downtown Old Saybrook
Apartment
Old Saybrook, Connecticut, USA

Welcome to Old Saybrook! Our apartment sits over our garage and is attached to our primary residence. It is conveniently located within walking distance to Main Street, the beach, local parks, and other town attractions. We have recently made many upgrades to the property and we're ready for guests! We look forward to sharing our home with you!

The space

The apartment is situated above our garage and has a private entry off the driveway. Guests will need to climb a flight of stairs to reach the living area. Adjacent to the living room is a dining area and kitchen. The bedroom is accessible at the end of the kitchen and has plenty of closet space for guests. The bathroom is accessible ONLY through the bedroom, so any guests staying in the living room will need to pass through the bedroom to reach the bathroom. The shower includes a large overhead skylight and massaging shower head. There is also a stacked washer and dryer inside the bathroom for guest use.

Guest access

Guests will have full access to the apartment. The backyard, including the enclosed dog run, is shared space and use must be coordinated with the owners. We have small children and occasionally watch dogs for friends. Backyard use requires that guests adhere to all property rules.

Interaction with guests

This is our home. Even if you don't see us, you'll probably hear our children from below. We are a friendly bunch and look forward to hosting friendly guests! Let us know how we can help make your stay more enjoyable.

Other things to note

Our children aren't always as quiet as we might like them to be. We want guests to be aware that our kids might be loud in the morning and the sound does travel to the apartment. We will provide white noise machines that should help you sleep later than we do! ;-)

Guest Reviews:

- "We had a delightful long weekend stay at this Cozy Cottage. The property was exactly as advertised. It has all the creature comforts of home. The bed was super comfortable and the linens and towels were a very good quality. The location was perfect, an easy walk to downtown restaurants and a very short drive to the beach. Kelly and Lee were great hosts, they were very responsive to all our communication. " - "Wonderful!! Prefect get away for 2!! Everything you need."

Apartments in Old Saybrook
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Apartment
Madison, Connecticut, USA

Come stay on the closest property to Hammonasset Beach State Park in all of Madison! Just 1 mile and your feet are on the beach, with two miles of white sandy beach to relax, explore, and enjoy.

Walk across the street to the Greenway Trail and stroll the scenic mile of gorgeous marsh and ocean views leading to the beach, or head just 1.5 miles into downtown Madison for shops, restaurants, and charm.

This peaceful 1.5-acre property includes two rentals:

There is the main house and the this fully renovated, modern carriage house apartment — located just 50 feet from the main home but fully private.

The apartment features:
• Private entrance
• Fully equipped kitchen
• Outdoor deck and fire pit
• Separate patio with dining area
• Beautiful yard surrounded by trees

The entire space is yours. The only shared space is the driveway.

Whether you're here for a romantic beach getaway or a quiet coastal retreat, you’ll love the privacy, location, and charm of this hidden gem. Book your stay today and enjoy the best of beachside Madison!

Guest Reviews:

- "My husband and I stayed here with our 3 month old infant while visiting family in the area. We brought our own crib and baby supplies but besides that the property had everything we needed and was really clean, comfortable and nicely decorated. Would definitely recommend to others." - "This place is exactly as described. Was absolutely perfect, cozy, and comfortable. Thanks Kevin!" - "I’ll be returning here whenever there’s no room to stay at Mom’s house. Immaculate, light-filled rooms with comfy new furniture, bedding — what a treat. The kitchen has everything you might need and the host has provided basic items that will please dog-owners and “I forgot to pack X” packers. The location is a stone’s throw from the beach and a nice walk into charming downtown Madison."

Apartments in Old Saybrook
Walk To Goodspeed Opera House!
Apartment
East Haddam, Connecticut, USA

Stay In The Heart Of East Haddam!--Home Of The Historic Goodspeed Opera House and The Gelston House. Step out the door of this private 2 bdrm/1 bath apartment and you are on the main street of East Haddam right on the Connecticut River and a stone's-throw from Goodspeed Opera House. Walk to everything. Step back in time as you soak in the colonial vibe. Truly breath-taking!
There are two bedrooms each with a king sized beds. A sofa in the living room area can comfortably fit one adult or 2 smaller children. Sofa is not a pull-out queen but rather the back flattens to about the size of a double bed. The bathroom is light and bright with marble floors and a marble shower. No bathtub. Hairdryer is provided in the bathroom cabinet. There is a nice-sized galley kitchen with frige, stove, toaster and microwave. There is Keurig and complimentary coffee. The combined dining and living area is a wonderful gathering space for socializing. Both bedrooms are large with closets for hanging clothes. For extra convenience there is a laundry area with washer and dryer! Step outside to your off-street parking lot and walk up the driveway. You are steps away from Goodspeed Opera House. In addition, the apartment faces East so on a sunny day you will wake up to plenty of sun pouring into the apartment!
The apartment has a lockbox with a key for entry. A code to the lockbox will be made in a message the day before arrival.

Extra linens, blankets and pillows are available on the shelves in the bedroom closets. Extra towels will be in the bathroom cabinet next to the sink.

Guest Reviews:

- "Such a clean, cozy, comfortable stay and a great location in town. We loved it! The beds were so comfortable, too, and communication with the host was lovely and easy!" - "If you are visiting for a show at the Goodspeed Opera House or just looking for a convenient spot to stay and enjoy the river valley, this is a great place. Walking distance to the inn and theater, and easy over the bridge and all directions up and down the river. Enjoy!"

Apartments in Old Saybrook
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Apartment
Haddam, Connecticut, USA

Keep it simple at this peaceful and centrally located apartment! Completely open concept and fully renovated. Plenty of off street parking. Come get away at our home away from home and just relax!!!!

Guest Reviews:

- "Owner provided every "convenience imaginable!! The space was decoraterd like a room from a magazine. She had snacks, coffee, plenty of water bottles. We really enjoyed our stay & visiting with the owner. She alone is 5 star!!!!" - "Restful and quiet" - "This was the perfect place for us to stay. We were in town for a wedding and our accommodations were far superior to our family who stayed in hotel rooms. Kristen and August were wonderful hosts and even left us a bottle of champagne as we were also celebrating our own wedding anniversary. The place was immaculate and the neighborhood was so quiet and peaceful. We will definitely be back!"

Apartments in Old Saybrook
The Millhouse Downtown Chester
House
Chester, Connecticut, USA

An upscale destination with accommodations for foodies & friends in the heart of historic Chester CT. Stay at this beautifully renovated historic Millhouse in charming downtown Chester. Enjoy strolling the streets loaded with shops, award winning restaurants, a microbrewery, art galleries, and more. All within a 1 minute walk. Our prime location is just 20 minutes to the CT shoreline and located in the heart of the CT River Valley. The Millhouse is next door to the Chester Historical Museum.

The space
This completely and beautifully restored, upscale apartment is on the ground level of an historic 200 year old Millhouse. Have your morning coffee by the waterfall or make breakfast in our foodie-friendly gourmet kitchen.

The smells emitting from across the brook (Grano - "One of CT’s best restaurants”) will have you making dinner reservations early and often.

Sit by the brook in our Adirondack armchairs at the fire-pit to sounds of the waterfall as you reflect on your days' adventures.

The apartment is over 1000 square feet of living space, contains a large, well-appointed gourmet kitchen and a full-size washer/dryer.

Every detail has been considered for your comfort. including soft warm throws, and eclectic designed bedrooms with the finest quality mattresses & bedding!

Guest Reviews:

- "The Millhouse is a lovely rental. Private and a very short walk to downtown Chester. The beaches are not far away and Gillette Castel close by. A nice relaxing place to stay." - "This was a perfect property for our family of four. Chester is such a quaint town with cute shops and great restaurants within close walking distance of the property. The area felt safe and small enough for our older teens to venture out on their own without worry. The air mattress was easily inflated to accommodate one of our two teens (they don’t like to share space). AC was a little too cool during the day but great in the evenings when sleeping. All amenities were available. Overall this was a great, centrally located area with all the amenities of home in a charming historic town with great food and ice cream (Honeycomb). We would definitely stay again!"

Apartments in Old Saybrook
Quiet Killingworth Rental w/Deck & Grill!
Apartment
Killingworth, Connecticut, USA

Seeking a tranquil escape? Look no further than 'Pond View Farm,' a lovely 1-bedroom, 1-bath apartment in Killingworth, CT! Perfect for couples or solo travelers, this vacation rental is nestled on a small farm surrounded by the beauty and abundance of nature. Hike in Chatfield Hollow State Park, relax on the pristine shores of East Wharf Beach Park, or take a ride on the Essex Steam Train & Riverboat. When evening comes, enjoy the sights and sounds of the stream as you grill out with your crew!

-- THE PROPERTY --

Pond & Stream Access | Ample Outdoor Seating | Hiking Trails (On-Site) | Close Proximity State Parks

Bedroom: Queen Bed | Living Room: Twin Daybed w/ Twin Trundle

SHARED AMENITIES: Backyard w/ animals on-site (horse, goats, chickens), back deck w/ seating, picnic table, charcoal grill, hiking trails
MAIN FEATURES: Smart TV (bedroom), cable TV (living room), electric fireplace, board games, books, ceiling fans, gas grill (propane provided)
KITCHEN: Cooking basics, refrigerator, microwave, stove/oven, blender, toaster, coffee bar w/ coffee maker & hot water kettle
GENERAL: Free WiFi, linens/towels, window A/C unit, central heating, hair dryer, hangers, iron/board, trash bags/paper towels, complimentary toiletries
FAQ: Homeowner on-site (main house), no fence around pond, 8 external security cameras (facing out)
ACCESSIBILITY: Stairs + unpaved walkway required for entry (single-story unit)
PARKING: Driveway (2 vehicles), RV/trailer parking allowed on-site

-- THE LOCATION --

EXPLORE OUTDOORS: Parmelee Farms (2 miles), Chatfield Hollow State Park (5 miles), Cockaponset State Forest (7 miles), Millers Pond State Park (8 miles), Scotts Farm (11 miles), Connecticut Valley Railroad State Park (12 miles), Wadsworth Falls State Park (13 miles), Gillette Castle State Park (16 miles), Lynman's Orchard Golf (16 miles), Ferry Landing State Park (17 miles), Black Birch Golf Course (18 miles), Portland Golf (20 miles)
FUN IN THE SUN: East Wharf Beach Park (11 miles), Hammonasset Beach State Park (11 miles), Clinton Town Beach (11 miles), Jacobs Beach (14 miles), Harveys Beach (20 miles), East Haven Town Beach (26 miles)
SEE & DO: Clinton Premium Outlets (8 miles), Ivoryton Playhouse (11 miles), Essex Steam Train & Riverboat (12 miles), Connecticut River Museum (13 miles), The Kate - Katherine Hepburn Cultural Arts Center (13 miles), Godspeed Opera House (13 miles), Niantic (19 miles), Mohegan Sun Casino (37 miles), Mystic Historic Seaport, Aquarium & Museum (39 miles)
DAY TRIPS: Watch Hill (50 miles), Newport, RI (94 miles), New York City (103 miles)
AIRPORT: Bradley International Airport (45 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: This single-story unit requires stairs and an unpaved walkway for entry
- NOTE: The homeowner lives in the main house on-site, with a completely separate and private entrance, and may be present during your stay
- NOTE: The property may not be suitable for young children due to the unfenced pond area
- NOTE: Your safety matters. This property features 8 exterior security cameras: 2 cameras are in the front of the house facing the front exterior, 2 cameras are in the back of the house facing the back exterior, 3 cameras are on the side facing the driveway, 1 camera is by the riding ring on the side of the house facing the riding ring, and 1 camera is at the basement entry facing the outdoor entry. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion

Guest Reviews:

- "Great location, close to family Special day " - "I really enjoyed my stay here. The house was cozy and comfortable with all the amenities you might need. A nicely appointed kitchen, a large living room with beautiful views of the pasture and pond, and a separate bedroom with large closet. Checkin and checkout was straightforward. John was a gracious host. Highly recommend!" - "My family stayed at this property during a visit home in CT. They had nothing but great things to say. Beautiful property, clean and comfortable home, check in process was easy and owners on premises were helpful and kind. Thank you! "

Apartments in Old Saybrook
Downtown, Main Street, Center of it All Location
Apartment
Old Saybrook, Connecticut, USA

Second Floor apartment in a historic building. Tastefully furnished and updated with a brand new kitchen, open floor plan, and washer/dryer. Enjoy the fresh air from the back porch. The building is next to the Katherine Hepburn theater (The Kate) and museum. Walk to area restaurants, pickle ball and basket ball courts, the town green and gazebo and unique local shops. Five minute drive to town beaches. Frozen yogurt, Benn & Jerry's, and Starbucks all within walking distance.

* Back of property in the parking area is scheduled for renovation that will include an improved parking surface, professional landscaping and a blue stone patio. While these changes are pending the area is not as aesthetically pleasing as it will be but in no way does this interfere with the usability of the location and charm of the apartment.

Guest Reviews:

- "We loved our stay! Clean, cute and centrally located. Steve welcomed us at the property upon arrival. Everything we needed for our short 2-night stay for a wedding!" - "Great stay. Hosts were accessible and helpful. Lots of fun things to do. Very relaxing." - "We booked here to see a show at the Kate - which is literally next door. Our show was cancelled, but our trip to Old Saybrook was still a great success! I live on the north shore of Massachusetts and my best friend lives in Central Jersey. This is about halfway between us. The location of the apartment is great is you are seeing a show at the Kate, but also just to sightsee around Old Saybrook. We had dinner at Nori one night, which is downstairs from the apartment - amazing sushi. We had “dinner” the second night at Sip. A leisurely early evening of charcuterie from the most amazing cheese store, Fromage, and wine flights of interesting and really tasty wines. Main Street has cute little shops and places to eat. The apartment was spotless! It has everything you need in a home away from home. We really enjoyed the pergola patio area with twinkle lights and very comfy outdoor furniture. Steve was welcoming and so easy to communicate with. We will definitely stay here again."

Apartments in Old Saybrook
Life on the Farm
Apartment
Killingworth, Connecticut, USA

Imagine living on a horse farm! Enjoy the wildlife, and watch horses graze right from your steps. Relax, at this unique getaway. As you drive down the entry to Fortunato Farm, you’ll feel a level of comfort allowing relaxation. Open the door, sip your coffee in the sunshine. You're in the country, yet close to CT shoreline areas and restaurants, Clinton Town Beach, and only 15 minutes to Middletown. 25 Miles to Tweed Airport and 45 Miles to Bradley International. 37 miles to Mystic & Mohegan.

Located on a 26 acre horse boarding facility. This is not only our home but we house other people’s horses. There is typically someone always around.

Coming with your horse? We can help accommodate them too for an additional fee. We also offer lessons and may have availability if booked ahead of time. Message Brittany for more information.

Morning chores start between 6:30 and 7:00 AM, so you may hear equipment outside and horses neighing!! As the weather gets nicer too, you could see people riding their horses around or walking them - please be mindful!

Guest Reviews:

- "There's no better place to stay if you don't have to be out and about until later in the day and want to have a peaceful morning communing with nature and the farm critters!" - "This was a great place to stay for us with our St Bernard during a dog competition weekend. Clean, comfortable bed, space to walk the dog in the morning—it hit the mark. Though we did not use it, the kitchen looked adequate for basic use, and there was a coffee maker with pods available."

Apartments in Old Saybrook
Shoreline Oasis
Apartment
Clinton, Connecticut, USA

Keep it simple at this peaceful little oasis located in a quiet neighborhood, but close to all the fun stuff! We are a 5 min drive to beautiful beaches at Hammonassett State Park, a 6 min drive to Chamard Vineyards and close to many other lovely bars/restaurants. We are walking distance to Clinton’s little downtown, the train station (can easily get to New Haven and NYC) and the waterfront, where you can hit up Lobster Landing- Clinton’s very own home of the greatest lobster roll in New England!

Interior:
When you enter through the front door, you will see an old style bannister stairway and stacked washer dryer, which you are welcome to use during your stay. Go up the stairs and find our wall of postcards with helpful tips about your stay at the top of the stairs. Enter the cozy, light-filled bedroom with FULL size bed on the left and take a deep breath, start to relax some, you’ve made it. Go right at the top of the stairs and you will find the small bathroom straight ahead with a standup shower (great water pressure), toilet and tiny sink. Keep exploring through the doorway next to the bathroom and you will find a well appointed, large living room with two very comfortable white couches (not pull-out). There are a few personal touches and plants that give some character and show the true personality of this space. There is also a TV that is hooked up to Netflix and Hulu. Next, you will find the eat-in kitchen with full fridge, microwave, Keurig coffee machine, toaster, oven, electric stovetop, sink, dish rack, garbage bins, pantry and table for four. There are smoke/carbon monoxide detectors throughout, fire extinguisher under kitchen sink, ceiling fans in all rooms, and an A/C unit in the bedroom and living room.

Guest access:
Enter through the FRONT DOOR and have access to the entire UPSTAIRS and front porch.

About your host:
My family and I live downstairs in a SEPARATE apartment, so the likelihood of bumping into one another is fairly good. That being said, we will be as interactive as you wish. Chances are, if you’re here on the weekend, we’ll be outside gardening. Feel free to say hi and we’ll be happy to offer suggestions for things to do in the area. Maintaining your privacy and making sure you have a lovely stay are of the utmost importance.

One thing we do ask you to keep in mind is our apartments are separated by a locked door. Please keep the noise level down and absolutely no parties as we do work a regular 9-5 job. Thank you! :)

Other things to note...

Restaurants recs nearby:

If you’re looking for outdoor and on the water there’s Aqua- which is walking distance from my place, nothing fancy, but a town favorite for outdoor casual dining. Then, there’s Madison Beach Hotel which is definitely fancier, food is good and drinks are strong lol.

Our favorite Irish pub type place with really good food is Donahue’s. They do have an outdoor seating area, but that’s nothing special. We go there to sit at the bar, watch sports and get a great meal- NE clam chowder is bomb!

Madison has a lot of nicer options, like Bar Bouche- delicious French food, Comomango- yummy Mexican with a fun vibe.

Some great summer/seasonal spots are Lobster Landing- shoreline’s best lobster roll, also walking distance. And there’s Johnny Ad’s in Old Saybrook- known for their burgers and fried seafood- when you're done eating, pop over to Fenwick’s ice cream!

Lmk if you need anymore!

Guest Reviews:

- "Stayed here to visit my daughter who just moved to CT. It’s in a great neighborhood and you can walk to the water. We did and ate at Lobster Landing- yum! Only about 30 minutes to New Haven too. Beautiful gardens, great front porch, comfy bed, and a quiet neighborhood that let us sleep so well . Host was so kind. Will look at staying again when we return to see my daughter. " - "The house and town were adorable. The space was the second floor. It was clean and and comfortable. "

Apartments in Old Saybrook
Contemporary Loft Apartment
Apartment
Westbrook, Connecticut, USA

Spacious loft style apartment located on second floor with views of Long Island Sound. Single bedroom with Queen size bed, full eat in kitchen equipped with dishwasher, microwave, coffee pot and small wares. Open living room with pull out sofa, TV, cable and internet service. Situated on private Chapman Beach in Westbrook. Guests can enjoy an afternoon swim on a private beach within a 2 minute walk and later watch the sun set from private balcony. Spend the day away enjoying the nearby attractions such as Outlet Shopping, Historic Essex, Train and River Boat Cruises, Antiquing in Old Saybrook, Gillette Castle or Goodspeed Opera House, Public Golf Coarse, Movie theaters, Miniature Golf. Fishing or Hiking along the shoreline or just walking around the nearby marinas. Short 30 minute drive to the casinos. Enjoy dining from casual to formal within a short drive.

Guest Reviews:

- "We enjoyed the month of August at this property including Chapman Beach, neighboring restaurants in Westbrook and Old Saybrook and local activities. Would definitely recommend." - "The location was perfect, nice views and one minute to the beach. It had everything that was needed to make me comfortable including an air conditioner and washer and dryer. It is a one bedroom but still spacious for company to visit. Loved that there were two decks, one in the front and one in the back. Lots of wildlife to enjoy watching. Looking forward to staying here again!"

Apartments in Old Saybrook
Beautiful Period Intact Victorian Apartment in East Haddam, CT
Apartment
East Haddam, Connecticut, USA

This is a charming c1850 Victorian home in the historic district of East Haddam. Most of its period details like first growth yellow pine floors, ornate trim, fireplaces adorned with Doric columns, original plaster crown moldings and like that has been lovingly restored to its original splendor while adding all the modern conveniences to support your modern lifestyle. Our town is home to three world class state parks, hosts of hiking trails, the Goodspeed Opera House and CT River.

The space
Large rooms, fully equipped kitchen, high-end appliances, antique plank floors, villa style tile flooring, washer/dryer, two full bath bathrooms, walk-in shower, claw foot tub. Two wonderful large bedrooms, and queen Murphy bed in our flex room sleeping a total of 6. UDH TV and gigabit internet with a high speed mesh network.

Guest access
We are set upon 2.25 fairly level and clear acres. Our home is shared by another rental suite on the premises along with 3 permanent tenants in other units and buildings on site. The rear blue stone and Astroturf patio with pergola and outside dining is served by a Weber gas grill.

Guest Reviews:

- "We had a very comfortable stay. E we’re most impressed with how nicely every room was appointed. Very welcoming and enjoyable." - "The location of the property was perfect for our needs. Very easy to get around the area and to our son’s boarding school. Communication w/ owners was excellent. Quick responses and kept us up-to-date with issues. We were traveling with in-laws, who have mobility issues. Entering property was easy to maneuver with walkers. It’s a first-floor rental all on one level, one of our criteria for renting. Check in - super easy. Owners notified us that the stove was being replaced, which was completed before we got there. We were not using it, so we had no issue with that. We were also informed that the second bathroom was being grouted and it would need to cure before using. Upon arrival, we learned that it would not be completed that day. We were ok w/ it as long as it was finished the next day. Needless to say, it was not completed, so we had 1 bathroom for 4 adults. Other issue was that the area was experiencing an unusual heat wave for October. They had actually removed the AC window units a few days prior so we had no AC. We arrived to a 75 degree apartment. It never cooled that night as it was so warm and humid outside. They did respond quickly and directed us to fans. The next day wasn’t better as it was 74. Sleeping with 1st floor windows open was unnerving but necessary to get any airflow. As these issues were 2 of my criteria, it was disappointing. Owner very responsive and offered partial refund. Lovely ppl. Would rent again if issues fixed. Very charming place!!"

Old Saybrook Family Friendly Apartments

Old Saybrook Apartments with Parking

Old Saybrook Pet Friendly Apartments

Old Saybrook Apartments with Entertainment

Old Saybrook Apartments with Private Pool

Old Saybrook Apartments with Private Beach

Old Saybrook Apartments on the Map

Compare the Best Apartments in Old Saybrook – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
The Millhouse Downtown Chester 5 West Main Street, Chester, CT, CT 06412, USA 294 4.0 10.0 2 Click here
Renovated 1 bedroom Cozy Apt-Madison Madison, Connecticut, USA 198 4.0 10.0 2 Click here
Cozy apartment, private beach & jacuzzi 89 Old Kelsey Point Road, Westbrook, CT, CT 06498, USA 168 3.0 9.5 8 Click here
Cozy apartment with a bird's eye view of Chester. 5 minute walk downtown Chester, Connecticut, USA 187 2.0 9.4 6 Click here
Walk To Goodspeed Opera House from this quaint 2 BDRM APT 2 Norwich Road Rear, East Haddam, CT, CT 06423, USA 283 3.0 9.0 6 Click here
The little Chestnut. A charming historic apartment in Downtown Chester Chester, Connecticut, USA 263 2.0 10.0 6 Click here
Quiet Killingworth Rental with Deck and Grill! Deep River, CT, USA 278 3.0 1 Click here
Newly Renovated Guest Suite - Steps to West Beach! Westbrook, Connecticut, USA 318 2.0 9.4 3 Click here
Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town Madison, Connecticut, USA 190 10.0 86 Click here
Convenient and cute in Downtown Old Saybrook Old Saybrook, Connecticut, USA 152 9.6 48 Click here
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn Madison, Connecticut, USA 356 10.0 36 Click here
Walk To Goodspeed Opera House! East Haddam, Connecticut, USA 198 9.4 34 Click here
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown Haddam, Connecticut, USA 256 10.0 26 Click here
The Millhouse Downtown Chester Chester, Connecticut, USA 310 9.8 23 Click here
Quiet Killingworth Rental w/Deck & Grill! Killingworth, Connecticut, USA 194 10.0 13 Click here
Downtown, Main Street, Center of it All Location Old Saybrook, Connecticut, USA 250 5.0 13 Click here
Life on the Farm Killingworth, Connecticut, USA 152 9.8 7 Click here
Shoreline Oasis Clinton, Connecticut, USA 211 9.2 7 Click here
Contemporary Loft Apartment Westbrook, Connecticut, USA 171 9.8 6 Click here
Beautiful Period Intact Victorian Apartment in East Haddam, CT East Haddam, Connecticut, USA 243 9.8 6 Click here

Note: The prices for each Apartments in Old Saybrook 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

Serviced apartments in Old Saybrook with pool access include:

  • Convenient and cute in Downtown Old Saybrook.- Review Count: 48, Rating: 9.6
  • Spacious 1-Bedroom Apartment surrounded by Woods.- Review Count: 0, Rating: 0.0

Family-friendly apartments in Old Saybrook include:

  • The Millhouse Downtown Chester.- Review Count: 2, Rating: 10.0
  • Renovated 1 bedroom Cozy Apt-Madison.- Review Count: 2, Rating: 10.0
  • Cozy apartment, private beach & jacuzzi.- Review Count: 8, Rating: 9.5

Pet-friendly apartments in Old Saybrook include:

  • Convenient and cute in Downtown Old Saybrook.- Review Count: 48, Rating: 9.6
  • Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn.- Review Count: 36, Rating: 10.0
  • Life on the Farm.- Review Count: 7, Rating: 9.8

Serviced apartments in Old Saybrook that offer breakfast include:

  • The Millhouse Downtown Chester.- Review Count: 2, Rating: 10.0
  • Historic Mansion, Gardens & Meadow.- Review Count: 0, Rating: 9.44

Apartments in Old Saybrook with on-site parking include:

  • The Millhouse Downtown Chester.- Review Count: 2, Rating: 10.0
  • Renovated 1 bedroom Cozy Apt-Madison.- Review Count: 2, Rating: 10.0
  • Cozy apartment, private beach & jacuzzi.- Review Count: 8, Rating: 9.5

Some of the best Apartments in Old Saybrook are:

  • Renovated 1 bedroom Cozy Apt-Madison.- Review Count: 2, Rating: 10.0
  • The Millhouse Downtown Chester.- Review Count: 2, Rating: 10.0
  • Cozy apartment, private beach & jacuzzi.- Review Count: 8, Rating: 9.5

Some of the popular Apartments in Old Saybrook are:

  • Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town.- Review Count: 86, Rating: 10.0
  • Convenient and cute in Downtown Old Saybrook.- Review Count: 48, Rating: 9.6
  • Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn.- Review Count: 36, Rating: 10.0