Best Vacation Rentals in Middlebury

Top Vacation Rentals in Middlebury

Plan your perfect getaway with our selection of vacation rentals in Middlebury. Each choice offers a blend of comfort and local charm, ideal for families and groups.

Vacation Rentals in Middlebury
Wyndham Southbury
Hotel
1284 Strongtown Road, Southbury, CT, CT 06488, USA

Located just off Interstate 84, this hotel is 2.6 miles from Quassy Amusement Park. The hotel features an on-site restaurant, a gift shop, and a free area shuttle. Free Wi-Fi and a flat-screen TV are included in every room at Wyndham Southbury. They are equipped with a coffee maker and furnished with a work desk. The on-site restaurant, the Arrowhead, serves American cuisine for breakfast, lunch, and dinner. Guests can relax in the indoor pool and sauna at the Wyndham Southbury. A modern gym and a business center are also located on site. Woodbury Ski Area is 10.3 miles from the hotel. The Timexpo Museum is 9 miles away.

Guest Reviews:

- "Friendly staff and clean establishment." - "8 days visiting family" - "I will stay again when traveling from Virginia to Maine" - "Quiet, comfortable, and nice room. However, the guy that checked us in was not very nice and we couldn’t get any new tow" - "It was convenient and well priced"

Vacation Rentals in Middlebury
Evergreen Bed & Breakfast
Bed & Breakfast
Southbury, Connecticut, USA

Guest Reviews:

- "I have visited many B &B’s and found this one the very best. The main reason being the owner’s attention to all the details that make it a fabulous visit." - "We had a great stay! The inn is a beautiful historic property. Brian knows all of the history and shared a bunch of interesting facts. Rooms are spacious and comfortable. The bar at the back of the inn is a great spot to hang out, great selection of craft beers, wines and spirits. Jen makes and amazing breakfast in the morning. Close to lots of activities and restaurants. Awesome place!"

Vacation Rentals in Middlebury
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection
Hotel
522 Heritage Road, Southbury, CT, CT 06488, USA

Nestled in the picturesque Litchfield Hills, this luxurious resort and spa offers classic New England charm and hospitality along with unrivaled services and amenities, and is moments from area attractions. Discover an endless variety of on-site activities, facilities and services at the Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection. Start the morning with breakfast at one of the on-site restaurants, then play a round of golf on the top-rated course. Spend the afternoon relaxing at the full-service spa or lounging by the pool. Finish the evening relaxing in spacious guestrooms, furnished with MP3 compatible radios and free high-speed internet access. In addition to on-site basketball courts, hiking trails and tennis facilities, the Heritage is also offers close proximity to area beaches and parks. Charming antique stores, unique museums and local restaurants are also only moments away. feet Athletic Club with an indoor salt water pool, men's and women's steam rooms and dry saunas as well as a seasonal outdoor salt water pool and pool bar. Relax at The Spa a full service relaxation retreat from facials to massages to nails we're here to pamper you. After your spa visit unwind at The Tavern with a creative cocktail or a local tap beer and indulge in a chef driven meal with weekly entertainment such as trivia and or live music. In the morning test your skills at the 9 the hole golf course or our tennis court or just enjoy the vineyard views or local art walk. Located just 2 hours from Boston and 1.5 hours from NYC, your rustic retreat is closer than you think. Your rustic retreat is just a click away, we can't wait to see you!

Guest Reviews:

- "Great stay" - "Beautiful Hotel" - "We frequently stay at The Heritage to visit family and this place is perfect for that." - "Would definitely stay here again." - "Friendly staff, food great, property clean. Everyone pleasant. Affordable. Definitely will tell friends and also come ag" - "Excellent" - "Please experience this place atleast once! It's amazing." - "Next time, I would like to have a room away from small children, they have too much energy."

Vacation Rentals in Middlebury
Courtyard by Marriott Waterbury Downtown
Hotel
63 Grand St, Waterbury, CT, 06702, USA

Hotel in Waterbury with a 24-hour fitness center and a 24-hour business center
Along with a restaurant, this smoke-free hotel has a 24-hour fitness center and a bar/lounge. WiFi in public areas is free. Additionally, a snack bar/deli, a 24-hour business center, and a coffee shop/cafe are onsite.
Housekeeping is available on request.
Courtyard by Marriott Waterbury Downtown offers 199 accommodations with safes and coffee/tea makers. 32-inch flat-screen televisions come with premium satellite channels. Bathrooms include separate bathtubs and showers, complimentary toiletries, and hair dryers.

This Waterbury hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and desk chairs, as well as phones; free local calls are provided (restrictions may apply). Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Change of towels and change of bedsheets can be requested. Housekeeping is provided daily.


Recreational amenities at the hotel include a 24-hour fitness center.

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

Guest Reviews:

- "There was literally nothing I didn’t like. It was a perfect, comfortable, and quiet stay; Will definitely be on the top of my recommendations for friends." - "Quiet... comfort... items in the pantry/store expensive" - "I’ve stayed here a few times and the rooms are comfortable clean, and the staff is friendly " - "We had a great stay. " - "Second time staying here in two months. Friendly and helpful service. Needed tape to wrap some presents which the front desk staff provided from their desk. Very much appreciated."

Vacation Rentals in Middlebury
Private Apt In Southfordsouthbury
Apartment
1455 Southford Road 2, Southbury, CT, CT 06488, USA

A recently renovated apartment, Private Apt In Southfordsouthbury offers accommodations in Southbury. Both free Wifi and parking on-site are accessible at the apartment free of charge. The Yale Bowl is 16 miles away and City Hall is 18 miles from the apartment. Private Apt In Southfordsouthbury features 1 bedroom, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with free toiletries. Towels and bed linen are available in the apartment. For added privacy, the accommodation features a private entrance. Dining options are available close to the accommodation. Guests can relax in the garden at the property. Flanders Nature Center is 12 miles from Private Apt In Southfordsouthbury, while Abbey of Regina Laudis is 13 miles from the property. Tweed-New Haven Airport is 22 miles away.

Guest Reviews:

- "We had a great time, Gabe was a great host and made sure to check in with us to be sure we had what we needed. I highly" - "Excellent, all around." - "Will definitely be booking this property again for a longer stay!" - "OUTSTANDING STAY!" - "Loved how big it was and the pool table was fun!" - "Full apartment for everything we need" - "Good. I’ll come again and stay at this apartment." - "Perfect for summer visit to the area."

Vacation Rentals in Middlebury
Wyndham Southbury
Hotel
1284 Strongtown Road, Southbury, CT, 06488, USA

Hotel in Southbury with area shuttle service and a fitness center
Along with an indoor pool, this hotel has a restaurant and a fitness center. Free WiFi in public areas, free self parking, and a free area shuttle are also provided. Other amenities include a bar/lounge, a snack bar/deli, and a business center.
Housekeeping is available on request.
Wyndham Southbury offers 193 air-conditioned accommodations with safes and complimentary newspapers. Beds feature premium bedding. Guests can make use of the in-room refrigerators and coffee/tea makers. Bathrooms include bathtubs or showers and complimentary toiletries.

Guests can surf the web using the complimentary wired and wireless Internet access. Flat-screen televisions come with premium cable channels. Microwaves, change of towels, and change of bedsheets can be requested. Housekeeping is provided daily.


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

Guest Reviews:

- "Very convenient " - "Nice place!" - "I liked the hotel" - "Clean and accessible " - "Accommodating and attentive staff. Convenient location. Room shows it’s age but clean. Would stay here again. " - "Very clean " - "The staff is welcoming and attentive." - "Not a bad place for the money" - "In my opinion that place is a good place to stay for a good trip. " - "Quick and easy check in" - "Nice place"

Vacation Rentals in Middlebury
Private studio guesthouse in Watertown CT
Apartment
144 Old Colony Rd, Watertown, CT, CT 06795, USA

Private studio guesthouse in Watertown CT offers accommodations in Watertown, 6.8 miles from Flanders Nature Center and 7.9 miles from Abbey of Regina Laudis. This apartment features free private parking, full-day security, and free Wifi. Staff on site can arrange a shuttle service. Featuring inner courtyard and quiet street views, this recently renovated apartment offers 1 bedroom and opens to a patio. The air-conditioned apartment also provides a flat-screen TV, a fully equipped kitchen with a microwave, a seating area, washing machine, and 1 bathroom with a walk-in shower. For added privacy, the accommodation has a private entrance and soundproofing. Outdoor play equipment is also available for guests at the apartment. Witch’s Dungeon Classic Movie Museum is 15 miles from Private studio guesthouse in Watertown CT, while Lake Compounce is 21 miles from the property. Tweed-New Haven Airport is 32 miles away, and the property offers a paid airport shuttle service.

Guest Reviews:

- "Absolutely fantastic, comfortable, clean, fantastic flexible and super kind host." - "Loved my stay and would totally recommend!" - "The hosts were very accommodating, the location was good and the studio was warm and welcoming." - "A perfect spot to return to after a busy day Iwould definitely book again"

Vacation Rentals in Middlebury
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection
Hotel
522 Heritage Rd, Southbury, CT, 06488, USA

Suburban hotel with a full-service spa and a golf course
A full-service spa, a golf course, and an indoor pool are available at this smoke-free hotel. Free WiFi in public areas and free self parking are also provided. Additionally, a health club, a bar/lounge, and a poolside bar are onsite.
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection offers 163 air-conditioned accommodations with MP3 docking stations and laptop-compatible safes. Pillowtop beds feature premium bedding. 42-inch flat-screen televisions come with premium cable channels and pay movies. Guests can make use of the in-room refrigerators and coffee/tea makers. Bathrooms include shower/tub combinations, designer toiletries, complimentary toiletries, and hair dryers.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include complimentary newspapers and phones; free local calls are provided (restrictions may apply). Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Housekeeping is offered daily and in-room massages can be requested.


Guests can play rounds at the 9-hole golf course and enjoy other recreation facilities including an outdoor tennis court and a health club. An indoor pool, a seasonal outdoor pool, and a hot tub are on site. Other recreational amenities include a sauna and a fitness center.

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

Guest Reviews:

- "Lovely " - "Absolutely amazing! " - "Great place " - "Great customer service" - "Staff was very understanding and friendly. " - "Had a death in the family and am from out of town. Beautiful hotel, clean and staff friendly and welcoming " - "Very convenient always comfortable and clean " - "The pooland jacuzzi was a plus!" - "Nice" - "Faculty has a lot to do! " - "F" - "Petfect as usual. Clean, comfortable and consistent. Always love the pub staff. Food, drink qnd service top notch. "

Vacation Rentals in Middlebury
Private Apt In Southfordsouthbury
Apartment
1455 Southford Road, Southbury, CT, 06488, USA

Private Apt In Southfordsouthbury offers accommodations in Southbury, 12 miles from Flanders Nature Center and 13 miles from Abbey of Regina Laudis. Both free Wifi and parking on-site are accessible at the apartment free of charge. Yale University is 18 miles away and Russian Railway Museum is 19 miles from the apartment. Private Apt In Southfordsouthbury features 1 bedroom, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with free toiletries. Towels and bed linen are offered in the apartment. For added privacy, the accommodation features a private entrance. Guests can relax in the garden at the property. The Yale Bowl is 16 miles from the accommodation, while City Hall is 18 miles from the property. Tweed-New Haven Airport is 22 miles away.

Amenities:

Child Friendly • Air Conditioner • Fireplace/Heating • Internet • Security/Safety • View • Pet Friendly • Parking

Vacation Rentals in Middlebury
Heart of Waterbury. Spacious. New. Office. Parking.
Apartment
Waterbury, Connecticut, USA

This special place is close to everything, making it easy to plan your visit.
*Whole apartment is being refurnish and newly decorated. Pictures are for sample*

What guests will LOVE:
-Perfect for a long-term stay
-Close to shopping, convenience stores, highways, hospitals, universities, parks.
-Amenities chosen for convenience
-Newly decorated
-Free Wi-Fi
-Ample private parking
-Outstanding hospitality
-Touch pad key entry
-Quiet and peaceful

This apartment is Non-Smoking. No Parties/Events.

Apartment includes stairs to access.

Amenities:

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

Vacation Rentals in Middlebury
Tidal Time Estate With Game Room And Lsv
House
49 Boswells Ct, Waterbury, CT, 32550, USA

Tidal Time Estate With Game Room And Lsv is located in Waterbury, just 7.5 miles from Flanders Nature Center and 8.6 miles from Abbey of Regina Laudis. This property offers access to a balcony, free private parking, and free Wifi. Witch’s Dungeon Classic Movie Museum is 13 miles from the vacation home and Lake Compounce is 17 miles away. Offering direct access to a patio, the vacation home consists of 7 bedrooms. The air-conditioned vacation home also features a flat-screen TV, a fully equipped kitchen with a dishwasher, a seating area, washing machine, and 6 bathrooms with a bath and a shower. The property has an outdoor dining area. Guests at the vacation home can enjoy cycling nearby, or make the most of the outdoor pool. The Yale Bowl is 26 miles from Tidal Time Estate With Game Room And Lsv, while City Hall is 27 miles from the property. Tweed-New Haven Airport is 30 miles away.

Amenities:

Security/Safety • Other • Parking • Pool • Air Conditioner • Internet • Balcony/Terrace • Fireplace/Heating • Sports/Activities • Laundry • Pet Friendly • View

Vacation Rentals in Middlebury
Charming Waterbury Gem w\/ Smart TVs Near Skiing!
Apartment
107 Wall St, Waterbury, CT, 06705, USA

Located in Waterbury, this welcoming apartment lets you experience it all. Brass Mill Center is an easy 10-minute walk away, so you can leave your car at the property, which offers onsite parking, or jump in your vehicle to make short work of the 2-minute drive to Palace Theatre.

As you settle into this 3-bedroom, 1-bathroom rental, you'll find a living room, air conditioning, and a ceiling fan. Connect to the free WiFi, or get cozy in front of the TV. The kitchen is equipped with an oven and a stovetop, as well as a coffee maker, a microwave, and cookware. Other amenities include bed sheets, an ironing board, and heating.

Amenities:

Child Friendly

Vacation Rentals in Middlebury
Spacious Woodbury Home with Pool and Hot Tub!
House
Woodbury, CT, USA

Spacious Woodbury Home with Pool and Hot Tub! is located in Woodbury, just 1.9 miles from Flanders Nature Center and 2.8 miles from Abbey of Regina Laudis. Guests can benefit from a patio and an outdoor pool. The accommodation offers a hot tub, free Wifi throughout the property, and a 24-hour front desk. The air-conditioned vacation home consists of 4 bedrooms, 3 living rooms, a fully equipped kitchen with a dishwasher and a coffee machine, and 3 bathrooms with a hot tub and a hair dryer. Towels and bed linen are offered in the vacation home. The property has an outdoor dining area. Witch’s Dungeon Classic Movie Museum is 18 miles from the vacation home, while Lake Compounce is 22 miles from the property. Tweed-New Haven Airport is 32 miles away.

Amenities:

Sports/Activities • Hot Tub • Internet • Fireplace/Heating • Oceanfront • Guest Services • View • Parking • Ocean View • Pool • Security/Safety • Other

Vacation Rentals in Middlebury
Blackwoods Old Country Home 5 Bedroom Home by RedAwning
House
279 Transylvania Road, Woodbury, CT, 06798, USA

Located in Woodbury, this welcoming vacation home brings it all within your reach. Jump into your car and make short work of the 5-minute drive to Hollow Park or the 4-minute drive to Glebe House Museum and The Gertrude Jekyll Garden (and enjoy the property's convenient onsite parking in the meantime).

Relax by the outdoor pool or sip a drink by the firepit of this vacation home, which also features a yard and a BBQ grill. For a change of scenery, come inside and enjoy the free WiFi.

No need to pay for a restaurant every night, when you've got an oven and a refrigerator on hand, as well as a coffee maker and a toaster. Bathroom amenities include towels and shampoo. And you won't have to pack extra clothes, because you'll have a washer and dryer, too.

Amenities:

Bedding/Linens • Laundry • Pet Friendly • Balcony/Terrace • Security/Safety • Barbecue/Outdoor Cooking • Child Friendly • Parking • Internet • Fireplace/Heating • Pool • Kitchen

Vacation Rentals in Middlebury
Courtyard Waterbury Downtown
Hotel
63 Grand Street, Waterbury, CT, CT 06702, USA

Located in downtown Waterbury, this hotel offers rooms equipped with flat-screen TVs and free high-speed internet access. Each accommodations at this Courtyard is features a work desk with an ergonomic chair for comfort. Other in-room amenities include a coffee maker, hairdryer and ironing facilities. At the center of the hotel’s lobby, guests can find a Bistro with many breakfast choices in the morning, dinner options during the evening and a quick bite all day long. Courtyard Waterbury Downtown is located at the intersection of Route 8 and I-84. It is 2.5 mi from Western Hills Golf Course and 12 mi from Compounce Amusement Park.

Guest Reviews:

- "Exceptional hotel staff, friendly and helpful!" - "Very pleasant and I was very happy with the service provided" - "Exceptionally personable staff." - "Excellent staff" - "Excellent hotel and location" - "Excellent" - "Stay was good overall" - "Will stay again" - "My stay was excellent, I’m happy with the outcome." - "Review l to bb to w2" - "Best hotel stay I’ve had in a long time" - "Comfiest beds ever"

Vacation Rentals in Middlebury
Hampton Inn Waterbury
Hotel
777 Chase Pkwy, Waterbury, CT, 06708, USA

Hotel in Waterbury with free breakfast and a fitness center
This hotel features a fitness center, a 24-hour business center, and coffee/tea in a common area. Free buffet breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, a business center, conference space, and laundry facilities are onsite.
Hampton Inn Waterbury offers 91 accommodations with safes and coffee/tea makers. Cable television is provided.

Bathrooms include bathtubs and hair dryers. This Waterbury hotel provides complimentary wired and wireless Internet access. Housekeeping is provided daily.


Recreational amenities at the hotel include a fitness center.

Guest Reviews:

- "It just so happens the Hockey teams where their." - "Very friendly staff and very professional. " - "Quiet and comfortable beds" - "Quiet room on 4th floor. Good breakfast. " - "Easy check in, clean room, great breakfast options." - "Outside of the noise above us (not sure what was going on but sounded like lots of moving of furniture) the room as always was a great stay. Comfy bed, cozy room. " - " The staff was absolutely fantastic!!. Everyone was extremely friendly and respectful. I truly appreciated the hospitality from Niles, Kevin, Shirley, and, Coco. My Room was clean and my bed was comfortable. I didn't have to deal with any loud noise which was a plus. I have to admit the highlight of my business trip was with a young man by the name of Prathon. He greeted not only myself but every guest that came in the breakfast area each morning. I watched him guard that buffet as if it was the President's kitchen. I was only going to drink a cup of tea because not all hotels keep a clean station. However he proved me wrong. The buffet was well lit and everything looked fresh. I enjoyed my breakfast each day and even had their red velvet waffles recommend by Prathon this morning before checking out. Thank you all very much for your amazing service and I look forward to seeing you soon. Thank you Prathon for your morning greetings and keeping that area so clean and inviting. "

Vacation Rentals in Middlebury
Hampton Inn Waterbury
Hotel
777 Chase Parkway, Waterbury, CT, CT 06708, USA

Hampton Inn Waterbury has accommodations in Waterbury. With free WiFi, this 3-star hotel offers a 24-hour front desk and a business center. The property is non-smoking throughout and is located 11 miles from Flanders Nature Center. The rooms will provide guests with a fridge. Abbey of Regina Laudis is 12 miles from the hotel, while Witch’s Dungeon Classic Movie Museum is 17 miles from the property. Tweed-New Haven Airport is 27 miles away.

Guest Reviews:

- "I would stay there again." - "Great service good breakfast loved it here" - "My stay was great." - "Magnificent" - "Very Good except for disturbing water in toilet and bath." - "Mrs Regina was awesome" - "Overall I had a great time y’all just need get that pool working I had a long day and wanted to swim" - "It was very nice." - "Very convenient, with a great breakfast." - "Nice property located in quiet setting"

Vacation Rentals in Middlebury
Comfort Inn Naugatuck-Shelton, CT
Hotel
716 New Haven Rd, Naugatuck, CT, 06770, USA

Hotel in Naugatuck with free breakfast and a 24-hour business center
A 24-hour business center, coffee/tea in a common area, and a meeting room are available at this smoke-free hotel. Free buffet breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, concierge services, dry cleaning, and laundry facilities are onsite.
Comfort Inn Naugatuck-Shelton, CT offers 50 accommodations with complimentary newspapers and coffee/tea makers. Beds feature premium bedding. LED televisions come with satellite channels. Bathrooms include complimentary toiletries and hair dryers.

This Naugatuck hotel provides complimentary wired and wireless Internet access. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Housekeeping is provided daily.

Guest Reviews:

- "Decent and convenient " - "I've enjoyed my stay here several times now. When I need to get away from it all. I come stay a few nights and enjoy myself. It's quiet and clean. And it's affordable. I'll definitely keep coming back." - "heater was a bit noisy and sounded malfunctional in room 223" - "When I have business in the area, this is where I stay. Front desk agents are very kind and friendly. Room is very nice and it is in a safe area."

Vacation Rentals in Middlebury
Comfort Inn Naugatuck-Shelton, CT
Hotel
716 New Haven Road, Naugatuck, CT, CT 06770, USA

Featuring free WiFi, Comfort Inn Naugatuck is 7.3 mi from Naugatuck Valley Community College. Free private parking is available on-site. All guest rooms have flat-screen TVs, coffee makers, hair dryers and ironing facilities. There is a business center, laundry facilities and fitness center on-site. A hot breakfast, featuring eggs, meat and yogurt, is served every morning. Afternoon tea is offered daily. The city of Naugatuck, Connecticut, which is 0.8 mi from the property, is located along the Naugatuck River, south of Waterbury. Several restaurants, cocktail lounges, entertainment areas and shopping venues are in the vicinity. Tweed New Haven Regional Airport is 24 mi away.

Guest Reviews:

- "Very surprised and pleased with the overall accommodations." - "This is my favorite hotel ever , I could I would given them a 100 starts , my favorite thing about it is that they are p" - "All in all, it was really a great visit!" - "Good value." - "A simple basic hotel, no frills" - "Very good overall." - "Superb location, lovely staff. But fix the exercise room!" - "It was fine for an overnight stay. We were happier with the hotel on our last visit."

Vacation Rentals in Middlebury
The Milestone Inn
Hotel
146 S Pomperaug Ave, Woodbury, CT, 06798, USA

Hotel in Woodbury with free parking
This smoke-free hotel features express check-out, free self parking, and free WiFi in public areas.
The Milestone Inn offers 10 air-conditioned accommodations with coffee/tea makers and designer toiletries. Refrigerators and microwaves are provided. Bathrooms include shower/tub combinations and hair dryers.

This Woodbury hotel provides complimentary wireless Internet access. Cable television is provided.

Guest Reviews:

- "The Milestone Inn is a comfortable, clean and well appointed motel room. The motel uses a contactless checkin with no staff on site which was a new experience for us. There was a local phone problem which rendered contacting the inn difficult prior to the stay. Rinal from the motel contacted us the day prior to the stay and walked us through the check in process and took care of any final questions including providing us with and alternate contact number. "

Middlebury Vacation rentals with Parking

Middlebury Family Friendly Vacation rentals

Middlebury Pet Friendly Vacation rentals

Middlebury Vacation rentals with Entertainment

Middlebury Vacation rentals with Private Pool

Middlebury Vacation rentals with Spa

Middlebury Vacation-Rentals on the Map

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

Property Name Address Price ($) Star Rating Review Count Book
Wyndham Southbury 1284 Strongtown Road, Southbury, CT, CT 06488, USA 112 4.0 7.6 794 Click here
Evergreen Bed & Breakfast Southbury, Connecticut, USA 245 4.0 4.91 11 Click here
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection 522 Heritage Road, Southbury, CT, CT 06488, USA 235 4.0 8.4 456 Click here
Courtyard by Marriott Waterbury Downtown 63 Grand St, Waterbury, CT, 06702, USA 102 3.0 8.4 1042 Click here
Private Apt In Southfordsouthbury 1455 Southford Road 2, Southbury, CT, CT 06488, USA 180 4.0 9.0 31 Click here
Wyndham Southbury 1284 Strongtown Road, Southbury, CT, 06488, USA 106 3.0 8.2 1030 Click here
Private studio guesthouse in Watertown CT 144 Old Colony Rd, Watertown, CT, CT 06795, USA 96 4.0 10.0 4 Click here
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection 522 Heritage Rd, Southbury, CT, 06488, USA 148 3.0 8.4 1005 Click here
Private Apt In Southfordsouthbury 1455 Southford Road, Southbury, CT, 06488, USA 176 4.0 10.0 1 Click here
Heart of Waterbury. Spacious. New. Office. Parking. Waterbury, Connecticut, USA 98 3.0 1 Click here
Tidal Time Estate With Game Room And Lsv 49 Boswells Ct, Waterbury, CT, 32550, USA 467 4.0 1 Click here
Charming Waterbury Gem w\/ Smart TVs Near Skiing! 107 Wall St, Waterbury, CT, 06705, USA 336 3.0 1 Click here
Spacious Woodbury Home with Pool and Hot Tub! Woodbury, CT, USA 661 4.0 1 Click here
Blackwoods Old Country Home 5 Bedroom Home by RedAwning 279 Transylvania Road, Woodbury, CT, 06798, USA 1628 3.0 1 Click here
Courtyard Waterbury Downtown 63 Grand Street, Waterbury, CT, CT 06702, USA 122 3.0 8.1 670 Click here
Hampton Inn Waterbury 777 Chase Pkwy, Waterbury, CT, 06708, USA 115 2.0 8.0 1001 Click here
Hampton Inn Waterbury 777 Chase Parkway, Waterbury, CT, CT 06708, USA 126 3.0 8.3 318 Click here
Comfort Inn Naugatuck-Shelton, CT 716 New Haven Rd, Naugatuck, CT, 06770, USA 112 2.0 7.8 729 Click here
Comfort Inn Naugatuck-Shelton, CT 716 New Haven Road, Naugatuck, CT, CT 06770, USA 331 3.0 7.7 183 Click here
The Milestone Inn 146 S Pomperaug Ave, Woodbury, CT, 06798, USA 119 2.0 8.8 190 Click here

Note: The prices for each Vacation-Rentals in Middlebury 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 Middlebury that include a pool include:

  • Wyndham Southbury.- Review Count: 794, Rating: 7.6
  • Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection.- Review Count: 456, Rating: 8.4
  • Wyndham Southbury.- Review Count: 1030, Rating: 8.2

Vacation rentals in Middlebury offering shuttle or transport options include:

  • Wyndham Southbury.- Review Count: 794, Rating: 7.6
  • Wyndham Southbury.- Review Count: 1030, Rating: 8.2
  • Private studio guesthouse in Watertown CT.- Review Count: 4, Rating: 10.0

These vacation rentals in Middlebury provide spa or wellness access:

  • Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection.- Review Count: 456, Rating: 8.4
  • Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection.- Review Count: 1005, Rating: 8.4

Family-friendly vacation rentals in Middlebury include:

  • Wyndham Southbury.- Review Count: 794, Rating: 7.6
  • Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection.- Review Count: 456, Rating: 8.4
  • Courtyard by Marriott Waterbury Downtown.- Review Count: 1042, Rating: 8.4

Pet-friendly vacation rentals in Middlebury include:

  • Wyndham Southbury.- Review Count: 794, Rating: 7.6
  • Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection.- Review Count: 456, Rating: 8.4
  • Private Apt In Southfordsouthbury.- Review Count: 31, Rating: 9.0

Vacation rentals in Middlebury that include breakfast options include:

  • Wyndham Southbury.- Review Count: 794, Rating: 7.6
  • Courtyard by Marriott Waterbury Downtown.- Review Count: 1042, Rating: 8.4
  • Wyndham Southbury.- Review Count: 1030, Rating: 8.2

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

  • Wyndham Southbury.- Review Count: 794, Rating: 7.6
  • Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection.- Review Count: 456, Rating: 8.4
  • Courtyard by Marriott Waterbury Downtown.- Review Count: 1042, Rating: 8.4

Some of the best Vacation Rentals in Middlebury are:

  • Wyndham Southbury.- Review Count: 794, Rating: 7.6
  • Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection.- Review Count: 456, Rating: 8.4
  • Private Apt In Southfordsouthbury.- Review Count: 31, Rating: 9.0

Some of the popular Vacation Rentals in Middlebury are:

  • Courtyard by Marriott Waterbury Downtown.- Review Count: 1042, Rating: 8.4
  • Wyndham Southbury.- Review Count: 1030, Rating: 8.2
  • Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection.- Review Count: 1005, Rating: 8.4