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Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Middlebury vacation rentals

A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

1. 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.
$125 nightly
The price is $141
Nov 16 - Nov 17
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
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, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
$124 nightly
The price is $139
Oct 20 - Oct 21
Total with taxes and fees
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.

3. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (11 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
$300 nightly
The price is $340
Oct 20 - Oct 21
Total with taxes and fees
Bear Retreat - 2-bedroom house in Waterbury
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.
$241 nightly
The price is $273
Oct 26 - Oct 27
Total with taxes and fees
Private Apartment in Southbury 101
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.
$238 nightly
The price is $270
Nov 5 - Nov 6
Total with taxes and fees
Private Apartment in Southbury 102
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

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.
$130 nightly
The price is $147
Oct 22 - Oct 23
Total with taxes and fees
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
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.
$474 nightly
The price is $537
Oct 20 - Oct 21
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A modern kitchen with white cabinets, a dining area with a black table and chairs, and a large window with curtains.

8. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
$260 nightly
The price is $295
Nov 17 - Nov 18
Total with taxes and fees
Private Apartment in Southbury 105
A spacious living room with large windows, a fireplace, and a view of the outdoors.

9. 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
$469 nightly
The price is $539
Oct 20 - Oct 21
Total with taxes and fees
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.

10. 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.
$128 nightly
The price is $144
Nov 3 - Nov 4
Total with taxes and fees
Cozy private room in a shared home with a Full-size bed and private bathroom.
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

11. 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, (6 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
$210 nightly
The price is $238
Oct 28 - Oct 29
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

12. 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.
$290 nightly
The price is $310
Oct 20 - Oct 21
Total with taxes and fees
All New Studio apartment in center of town
A modern living room with a dark sofa, a small side table, and a kitchen area with a refrigerator and microwave.

13. 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.
$173 nightly
The price is $195
Nov 2 - Nov 3
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

14. 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, (16 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$290 nightly
The price is $310
Oct 20 - Oct 21
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

15. #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.
$407 nightly
The price is $435
Oct 20 - Oct 21
Total with taxes and fees
#27- Luxury Collection
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

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, (20 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
$244 nightly
The price is $276
Oct 20 - Oct 21
Total with taxes and fees
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A compact kitchen with grey cabinets, a built-in microwave, a coffee machine, and a sink with a modern faucet.

17. 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.
$290 nightly
The price is $310
Oct 20 - Oct 21
Total with taxes and fees
All New Fully Furnished Cozy Studio
A kitchen with white cabinets, a black refrigerator, a double sink, and a window overlooking a wooded area.

18. 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
$189 nightly
The price is $214
Nov 18 - Nov 19
Total with taxes and fees
Serene Country Cottage
A spacious room with a wooden staircase, a dining area with chairs and a table, and a large window with a view of trees.

19. Bristol Condo Near ESPN HQ & Lake Compounce!

Bristol Condo Near ESPN HQ & Lake Compounce!
Bristol
Bristol Condo Near ESPN HQ & Lake Compounce!
A staircase with a wooden handrail and a white wall with a large, oval-shaped mirror.

20. 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.
$685 nightly
The price is $776
Oct 20 - Oct 21
Total with taxes and fees
Lakehaven • Hot Tub, Decks, Fires & More
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

8/10 Good
"We had a great stay. Friendly staff, clean room and good breakfast options."
Paul 1-night trip
Posted 1 hour ago
Best Western Executive Hotel Of New Haven - West Haven

Find out more about Middlebury

Everything you need to know about Middlebury vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlebury vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlebury vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlebury. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middlebury in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $267 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlebury rentals

At Expedia, we put the best Middlebury vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middlebury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlebury vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlebury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.