A multi-tiered waterfall cascading over dark rocks surrounded by lush greenery.

Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Middlebury vacation rentals

A white house with a wooden staircase leading to a porch.

1. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (39 reviews)
"Charles was super responsive and the bed was amazingly comfortable. Also the shower head great water pressure :-)"
United States
Lisbeth
The price is AED 347
AED 443 total
includes taxes & fees
20 Nov - 21 Nov
Cozy One Bedroom Apartment Centrally Located in Southbury
A two-story house with a porch, a front door with a wreath, and a small garden area.

2. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (13 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is AED 426
AED 1,201 total
includes taxes & fees
22 Nov - 23 Nov
Bear Retreat - 2-bedroom house in Waterbury
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

3. Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.2 out of 10, Wonderful, (7 reviews)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
The price is AED 415
AED 899 total
includes taxes & fees
1 Dec - 2 Dec
Private Apartment in Southbury 102
A view through a window with a clear sky and lush greenery outside.

4. Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.6 out of 10, Exceptional, (7 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
The price is AED 489
AED 991 total
includes taxes & fees
6 Dec - 7 Dec
Private Apartment in Southbury 101
A modern kitchen with white cabinets, a microwave, stove, and sink. There is a dining area with a table and chairs.

5. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
The price is AED 404
AED 509 total
includes taxes & fees
13 Nov - 14 Nov
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A modern kitchen with white cabinets, a dining area with a black table and chairs, and a large window with curtains.

6. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is AED 393
AED 870 total
includes taxes & fees
16 Nov - 17 Nov
Private Apartment in Southbury 105
A spacious living room with large windows, a fireplace, and a view of the outdoors.

7. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown
9.0 out of 10, Wonderful, (6 reviews)
"In town to visit our new grandchild. It was just my husband and me. It had more then enough room and was very comfortable."
United States
Elizabeth H.
The price is AED 804
AED 1,892 total
includes taxes & fees
10 Nov - 11 Nov
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A spacious living room with large windows, a fireplace, and a view of the outdoors.

8. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is AED 1,003
AED 1,980 total
includes taxes & fees
10 Nov - 11 Nov
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

9. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is AED 231
AED 479 total
includes taxes & fees
18 Nov - 19 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

10. 1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
United States
David G.
The price is AED 551
AED 1,409 total
includes taxes & fees
30 Nov - 1 Dec
1-bedroom vacation home 22 minutes from Quinnipiac University
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

11. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is AED 294
AED 1,715 total
includes taxes & fees
20 Nov - 21 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A modern living room with a dark sofa, a small side table, and a kitchen area with a refrigerator and microwave.

12. Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.0 out of 10, Wonderful, (26 reviews)
"Great place clean and quiet "
United States
James P.
The price is AED 441
AED 724 total
includes taxes & fees
7 Dec - 8 Dec
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
A modern apartment with a green sofa, a wooden dining table, and a kitchen in the background.

13. Modern Westville Home near Yale and Hospitals

Modern Westville Home near Yale and Hospitals
West New Haven
10.0 out of 10, Exceptional, (5 reviews)
"Very clean and comfortable space. Excellent location and parking was a plus. We have stayed here twice and would definitely recommend to friends or family. "
United States
Thomas B.
The price is AED 380
AED 885 total
includes taxes & fees
9 Dec - 10 Dec
Modern Westville Home near Yale and Hospitals
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and a dining area with a table and chairs.

14. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (21 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is AED 790
AED 971 total
includes taxes & fees
10 Nov - 11 Nov
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Interior

15. Château Blanc | Near Yale University

Château Blanc | Near Yale University
Dwight
8.6 out of 10, Excellent, (9 reviews)
"Perfect for a quick trip and one night stay!"
United States
Chris D.
The price is AED 296
AED 666 total
includes taxes & fees
10 Nov - 11 Nov
Château Blanc | Near Yale University
A spacious lobby with a large chandelier, a central round table with a vase, and a checkered floor.

16. Yale Deluxe Modern Apartment

Yale Deluxe Modern Apartment
Downtown New Haven
10.0 out of 10, Exceptional, (1 review)
"Great spot close to everything with a secure entrance to the building. Easy access to the unit Quick responses and good communication from the host. Great unit with lots of amenities! Definitely would stay here again and again!!"
United States
Anonymous traveler
The price is AED 337
AED 683 total
includes taxes & fees
10 Nov - 11 Nov
Yale Deluxe Modern Apartment
A modern kitchen with stainless steel appliances, a central island, and a built-in oven.

17. #27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is AED 925
AED 1,762 total
includes taxes & fees
22 Nov - 23 Nov
#27- Luxury Collection
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

18. One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.4 out of 10, Exceptional, (3 reviews)
"The property is immaculate and the service very responsive."
United States
Stephanie G.
The price is AED 280
AED 626 total
includes taxes & fees
30 Nov - 1 Dec
One bedroom in United States of America, New Haven
A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

19. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
8.8 out of 10, Excellent, (28 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The price is AED 253
AED 858 total
includes taxes & fees
29 Nov - 30 Nov
The Sun Filled Cozy Creamery
A modern hotel room with a bed, bedside table, lamp, desk, and window.

20. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Bethel
10.0 out of 10, Exceptional, (4 reviews)
"Quick check-in and a quiet room made sleeping easy here. Everything felt straightforward without hassle."
United States
Anonymous traveler
The price is AED 399
AED 459 total
includes taxes & fees
10 Nov - 11 Nov
1 Queen Bed | Non-Smoking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middlebury Hotel Reviews

Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

8/10 Good
"Staff is very friendly. Rooms and common areas are in need of updating, carpets in particular. Linens and bath are clean but room smelled a bit musty. On site tavern is fun. Lauren and Simon are great bartenders 😁. Breakfast is a bit pricey for a small buffet breakfast."
Karen 4-night trip
Posted 6 hours ago
Heritage Hotel, Golf & Conference Center

Frequently asked questions

Can I find vacation rentals in Middlebury?

Yes, there are vacation rentals in Middlebury close to Quassy Amusement Park, or you can go with a more remote option if you'd like a relaxing place to stay. Middlebury is known for its parks.

What's the top vacation rental in Middlebury?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental near Middlebury offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Middlebury?

Family-friendly attractions include Quassy Amusement Park, whereas Lake Quassapaug is a spot to enjoy the outdoors. In the larger area, you’ll find Palace Theatre and Beacon Falls Town Recreation Field.

What’s a vacation rental in Middlebury like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Middlebury. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family getaway.