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Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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, (36 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
The price is SAR 348
SAR 475 total
includes taxes & fees
8 Sep - 9 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
8.8 out of 10, Excellent, (11 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is SAR 413
SAR 550 total
includes taxes & fees
19 Aug - 20 Aug
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Coffee/tea maker, fridge, microwave, oven

3. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
10.0 out of 10, Exceptional, (4 reviews)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
The price is SAR 589
SAR 1,173 total
includes taxes & fees
11 Sep - 12 Sep
Private Apartment in Southbury 103
Interior

4. Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.0 out of 10, Wonderful, (6 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 SAR 552
SAR 1,122 total
includes taxes & fees
11 Sep - 12 Sep
Private Apartment in Southbury 102
Interior

5. 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 SAR 526
SAR 1,088 total
includes taxes & fees
18 Aug - 19 Aug
Private Apartment in Southbury 101
Interior

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 SAR 413
SAR 550 total
includes taxes & fees
9 Sep - 10 Sep
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Outdoor dining

7. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is SAR 547
SAR 878 total
includes taxes & fees
27 Aug - 28 Aug
The Perch in the Purchase -- Cozy, unique, and private
TV

8. 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)
"Best stay ever! Parking lot was easy; apartment was clean and felt like home. Bed comfortable. Would booked this apartment next trip. My only recommendation that was the kitchen did not have a toaster. "
United States
Linda v.
The price is SAR 443
SAR 1,107 total
includes taxes & fees
14 Aug - 15 Aug
Newly Remodeled 1-BR Close to Everything yet Very Private
1 bedroom, iron/ironing board, WiFi, bed sheets

9. 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)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is SAR 443
SAR 1,110 total
includes taxes & fees
15 Aug - 16 Aug
Once the old Schools house now a newly furnished Apartment
Exterior

10. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is SAR 443
SAR 1,110 total
includes taxes & fees
24 Aug - 25 Aug
All New 1BR with tons of Charm
TV

11. Tiny, Budget Friendly 1 Bedroom Central CT

Tiny, Budget Friendly 1 Bedroom Central CT
Southington
8.0 out of 10, Very Good, (1 review)
"There were minor cleaning issues in the bathroom, and my only/biggest complaint is the listing is misleading as it says you have no neighbors but the space is physically attached to a larger house and the driveway and entry/exit doors for both units open into the same small space. Additionally the front door has a large glass window with no curtains so you have absolutely no privacy. This is a direct conflict with the listing and I did bring this up to the landlord. That being said the location...
United States
Zackary G.
The price is SAR 337
SAR 782 total
includes taxes & fees
16 Aug - 17 Aug
Tiny, Budget Friendly 1 Bedroom Central CT
Smart TV

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, (22 reviews)
"Great place clean and quiet "
United States
James P.
The price is SAR 487
SAR 826 total
includes taxes & fees
26 Aug - 27 Aug
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
TV

13. All New Private and Cozy in great location

All New Private and Cozy in great location
Wallingford
8.8 out of 10, Excellent, (6 reviews)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
The price is SAR 443
SAR 1,106 total
includes taxes & fees
14 Aug - 15 Aug
All New Private and Cozy in great location
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 SAR 300
SAR 701 total
includes taxes & fees
18 Aug - 19 Aug
One bedroom in United States of America, New Haven
TV

15. All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
10.0 out of 10, Exceptional, (1 review)
"Clean & Comfortable, excellent accessibility to area restaurants & shopping.There was a hitch with my payment before check-in, the owner was helpful & communicative in resolving the issue.Overall, a great place to stay."
United States
Thomas S.
All new 1BR apartment with all the features you are looking for
Interior

16. 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, (13 reviews)
"The property was very clean and inviting and the owner was very welcoming and helpful!"
United States
Sarah
The price is SAR 807
SAR 1,045 total
includes taxes & fees
16 Aug - 17 Aug
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Coffee/tea maker, fridge, microwave, oven

17. Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay in town when visiting family! Kitchen was well stocked, location was convenient, & it had everything we needed!"
United States
Jennifer L.
The price is SAR 443
SAR 1,110 total
includes taxes & fees
9 Sep - 10 Sep
Fully Furnished 1BR Apartment
Dining

18. 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, (78 reviews)
"Spacious"
United States
Mehul
The price is SAR 488
SAR 856 total
includes taxes & fees
5 Sep - 6 Sep
Spacious 2 Bedroom apartment close to Yale Bowl
Interior

19. 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 Sun Filled Cozy Creamery
TV

20. 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 SAR 443
SAR 1,110 total
includes taxes & fees
10 Sep - 11 Sep
Newly Remodeled with deck. Close to town center
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

Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

10/10 Excellent
"As always my stay was excellent"
BRIAN 2-night trip
Posted 2 hours ago
Hilton Garden Inn Shelton

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?

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University: This vacation home rental near Middlebury is equipped with a patio, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

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 Seven Angels Theater.

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.