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

Middlebury Holiday 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 holiday rentals

A two-story house with a porch, a front door with a wreath, and a small garden area.

1. 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 HK$883
HK$2,525 total
includes taxes & fees
3 Nov - 4 Nov
Bear Retreat - 2-bedroom house in Waterbury
A white house with a wooden staircase leading to a porch.

2. 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 HK$784
HK$995 total
includes taxes & fees
10 Nov - 11 Nov
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior

3. 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 HK$2,142
HK$4,229 total
includes taxes & fees
3 Nov - 4 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.

4. 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 HK$1,718
HK$4,056 total
includes taxes & fees
3 Nov - 4 Nov
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

5. 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 HK$965
HK$2,018 total
includes taxes & fees
1 Dec - 2 Dec
Private Apartment in Southbury 102
A modern kitchen with white cabinets, a microwave, stove, and sink. There is a dining area with a table and chairs.

6. 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 HK$863
HK$1,087 total
includes taxes & fees
19 Nov - 20 Nov
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A view through a window with a clear sky and lush greenery outside.

7. 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 HK$1,028
HK$2,082 total
includes taxes & fees
16 Nov - 17 Nov
Private Apartment in Southbury 101
A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

8. Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
10.0 out of 10, Exceptional, (1 review)
"Pro Unit very clean, check in was easy and host was responsive to issues 24/7.Unit is large with new appliances in full kitchen.It is located in a beautiful rural area of CT. I highly recommend it"
United States
Daniel R.
The price is HK$1,028
HK$2,098 total
includes taxes & fees
1 Dec - 2 Dec
Private Apartment in Southbury 104
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

9. 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 HK$1,687
HK$2,073 total
includes taxes & fees
3 Nov - 4 Nov
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A hot tub in a covered outdoor area with a view of trees and a fence.

10. Lakehaven • Hot Tub, Decks, Fires & More

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
10.0 out of 10, Exceptional, (1 review)
"Great find!! Amazing views, house was superb!"
United States
Iva B.
Lakehaven • Hot Tub, Decks, Fires & More
A modern kitchen with white cabinets, a dining area with a black table and chairs, and a large window with curtains.

11. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is HK$996
HK$2,054 total
includes taxes & fees
17 Nov - 18 Nov
Private Apartment in Southbury 105
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 HK$875
HK$1,470 total
includes taxes & fees
3 Nov - 4 Nov
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
A modern kitchen with stainless steel appliances, a central island, and a built-in oven.

13. #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 HK$1,976
HK$3,763 total
includes taxes & fees
22 Nov - 23 Nov
#27- Luxury Collection
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

14. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (6 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is HK$1,883
HK$3,769 total
includes taxes & fees
18 Nov - 19 Nov
Escape to Bantam Lake- With Fireplace and Hot tub!
A spacious kitchen with wooden cabinets, a large island with stools, and a clock on the wall.

15. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is HK$2,415
HK$2,956 total
includes taxes & fees
3 Nov - 4 Nov
The Jefferson Guest House, Spacious, Special Views
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

16. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable with easy communication with host I recommend this unit to all who want to visit Wallingford or who desire to take the train to ny or Boston etc"
United States
DAVID B.
The price is HK$1,036
HK$2,336 total
includes taxes & fees
3 Nov - 4 Nov
All New Studio apartment in center of town
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

17. 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 HK$840
HK$3,923 total
includes taxes & fees
8 Nov - 9 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

18. 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 HK$494
HK$1,023 total
includes taxes & fees
9 Nov - 10 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
A staircase with dark carpeted steps and wooden handrails, a black leather chair, a wooden table with chess pieces, and a framed painting on the wall.

19. All New Fully Furnished Cozy Studio

All New Fully Furnished Cozy Studio
Wallingford Center
9.8 out of 10, Exceptional, (9 reviews)
"Clean and well designed apartment in a great location. Book here if you are interested as you won't have any regrets. Enjoy! "
United States
Rick C.
The price is HK$1,036
HK$2,336 total
includes taxes & fees
16 Nov - 17 Nov
All New Fully Furnished Cozy Studio
A modern kitchen with a wooden island, white cabinetry, and a ceiling fan.

20. New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"Clean & comfortable, in an architecturally unique setting. Great proximity to a variety of downtown shops & restaurants - check out Center Street Brewing Co. for some excellent beer."
United States
Thomas S.
The price is HK$1,036
HK$2,336 total
includes taxes & fees
16 Nov - 17 Nov
New Railside Residents
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

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Very convenient"
Yuxiu 4-night trip
Posted 8 hours ago
New Haven Hotel

Find out more about Middlebury

Search for holiday rentals in Middlebury on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlebury using one of the methods below:

  • View our selection of featured holiday rentals in Middlebury
  • Use the map to find apartments and other holiday homes in the Middlebury neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlebury while they last

Look no further and take a look at our great range of rental properties in Middlebury!

Frequently asked questions

Can I find holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Quassy Amusement Park, or you can select a more secluded option if you're looking for a relaxing stay. Middlebury is known for its parks.

What are some of the best holiday rentals that Middlebury has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Middlebury offers a fireplace, a patio and a BBQ 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 that 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 wider area, you’ll find Palace Theatre and Beacon Falls Town Recreation Field.

What’s a holiday rental in Middlebury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlebury. Holiday rentals feature extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip.