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Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Middlebury vacation rentals

Exterior

1. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is AED 324
AED 446 total
includes taxes & fees
27 Sep - 28 Sep
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior

2. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is AED 327
AED 449 total
includes taxes & fees
28 Sep - 29 Sep
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior detail

3. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (8 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is AED 477
AED 1,269 total
includes taxes & fees
8 Oct - 9 Oct
Bear Retreat - 2-bedroom house in Waterbury
Coffee/tea maker, fridge, microwave, oven

4. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"It was amazing , clean and awesome and good time"
United States
Michael
The price is AED 529
AED 1,077 total
includes taxes & fees
28 Sep - 29 Sep
Private Apartment in Southbury 103
Interior

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 538 total
includes taxes & fees
24 Sep - 25 Sep
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Interior

6. 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 433
AED 953 total
includes taxes & fees
28 Sep - 29 Sep
Private Apartment in Southbury 101
Coffee/tea maker, fridge, microwave, oven

7. Stylish Westville Apartment near Yale Campus

Stylish Westville Apartment near Yale Campus
West New Haven
8.8 out of 10, Excellent, (3 reviews)
"Convenient location & hosts"
United States
Northeast C.
The price is AED 357
AED 904 total
includes taxes & fees
27 Sep - 28 Sep
Stylish Westville Apartment near Yale Campus
1 bedroom, iron/ironing board, WiFi, bed sheets

8. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"This apartment was wonderful - clean, well stocked, and cute. Aside from the proximity to the train tracks (although earplugs were thoughtfully provided), the location was great - close to the highway and more importantly Dairy Queen."
United States
Becky P.
The price is AED 433
AED 1,071 total
includes taxes & fees
24 Sep - 25 Sep
Once the old Schools house now a newly furnished Apartment
TV

9. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is AED 433
AED 1,071 total
includes taxes & fees
24 Sep - 25 Sep
Newly Remodeled 1-BR Close to Everything yet Very Private
House (3 Bedrooms) | Interior

10. 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
2 Oct - 3 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Exterior

11. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
The price is AED 433
AED 1,071 total
includes taxes & fees
24 Sep - 25 Sep
All New 1BR with tons of Charm
Interior

12. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 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 921 total
includes taxes & fees
7 Oct - 8 Oct
The Sun Filled Cozy Creamery
TV

13. Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is AED 433
AED 1,071 total
includes taxes & fees
24 Sep - 25 Sep
Newly Remodeled with deck. Close to town center
1 bedroom, desk, iron/ironing board, WiFi

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

One bedroom in United States of America, New Haven
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
The price is AED 294
AED 686 total
includes taxes & fees
27 Sep - 28 Sep
One bedroom in United States of America, New Haven
Dining

15. Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (79 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
The price is AED 419
AED 777 total
includes taxes & fees
28 Sep - 29 Sep
Spacious 2 Bedroom apartment close to Yale Bowl
Coffee/tea maker, fridge, oven, stovetop

16. Serene Country Cottage

Serene Country Cottage
Woodbridge
8.0 out of 10, Very good, (11 reviews)
"We had a great one night stay here! The place is really cute, clean and comfortable. One of the greatest parts about the stay was the host, Trent. He was welcoming and VERY responsive to questions! "
United States
felicia
The price is AED 464
AED 787 total
includes taxes & fees
28 Sep - 29 Sep
Serene Country Cottage
Exterior

17. Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.2 out of 10, Wonderful, (16 reviews)
"Pretty close to Yale campus"
United States
Dongjian
The price is AED 397
AED 894 total
includes taxes & fees
27 Sep - 28 Sep
Bright Downtown Studio near Yale & East Rock!
Interior

18. 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 1,903 total
includes taxes & fees
24 Sep - 25 Sep
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Desk, iron/ironing board, WiFi (free), bed sheets

19. Yale Science Park 1BR | Free Parking

Yale Science Park 1BR | Free Parking
Dixwell
8.0 out of 10, Very good, (8 reviews)
"The property had everything needed and was a short distance to so many campus sites. Would definitely stay again."
United States
Natalie B.
The price is AED 397
AED 948 total
includes taxes & fees
13 Oct - 14 Oct
Yale Science Park 1BR | Free Parking
Smart TV

20. 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, (24 reviews)
"Great place clean and quiet "
United States
James P.
The price is AED 443
AED 733 total
includes taxes & fees
29 Sep - 30 Sep
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
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

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

8/10 Good
"The room was clean and very up-to-date decor-wise."
Karen 1-night trip
Posted 13 hours ago
Courtyard by Marriott Waterbury Downtown

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.