Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Middlebury vacation rentals

1 bedroom, iron/ironing board, WiFi, bed sheets

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, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ￥18,881
￥46,675 total
includes taxes & fees
Jun 6 - Jun 7
Once the old Schools house now a newly furnished Apartment
1 bedroom, desk, iron/ironing board, WiFi

One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
10.0 out of 10, Exceptional, (1 review)
"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 ￥12,001
￥28,962 total
includes taxes & fees
Jun 8 - Jun 9
One bedroom in United States of America, New Haven
Interior

Modern Studio Retreat

Modern Studio Retreat
Dwight
The price is ￥22,705
￥37,428 total
includes taxes & fees
Jun 19 - Jun 20
Modern Studio Retreat
TV

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
The price is ￥18,881
￥46,675 total
includes taxes & fees
Jun 6 - Jun 7
All new 1BR apartment with all the features you are looking for
TV

Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.

Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
Dwight
8.0 out of 10, Very Good, (2 reviews)
"The studio apartment is in a very convenient location. It is a lovely walk to Yale. Many restaurants just outside the door. My friends, who joined me for a meal, found parking easily. It was a plus having use of a parking pass for Dwight Street. We never had a problem getting a parking spot. We also loved being able to bring our two small pups with us. The bottle of wine was a thoughtful touch. "
United States
ELIZABETH M S M.
The price is ￥22,001
￥36,839 total
includes taxes & fees
Jun 14 - Jun 15
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (30 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 ￥14,401
￥19,761 total
includes taxes & fees
Jun 9 - Jun 10
Cozy One Bedroom Apartment Centrally Located in Southbury
Cookware/dishes/utensils

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.6 out of 10, Exceptional, (15 reviews)
"wonderful stay - great apartment and location and communication!"
United States
Anonymous traveler
The price is ￥17,441
￥44,641 total
includes taxes & fees
Jun 10 - Jun 11
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Exterior

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is ￥23,201
￥54,003 total
includes taxes & fees
Jun 9 - Jun 10
Angelica’s safe haven @ west haven
Lobby

Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, Very Good, (8 reviews)
"The place was incredibly clean. The instructions were clear for entering and locking up. Great experience! Thanks Dylan. "
United States
Andrew P.
The price is ￥18,001
￥40,663 total
includes taxes & fees
Jun 7 - Jun 8
Spacious Bohemian Nook
Dining

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, (73 reviews)
"Spacious"
United States
Mehul
The price is ￥20,801
￥37,122 total
includes taxes & fees
Jun 7 - Jun 8
Spacious 2 Bedroom apartment close to Yale Bowl
Smart TV

Cozy Stay by Little Italy & Wooster Street

Cozy Stay by Little Italy & Wooster Street
Mill River
10.0 out of 10, Exceptional, (2 reviews)
"This apartment in a 4 unit building with its own parking lot was on a quiet street. Easy to get to no matter what side of the city I came from and close enough to walk to downtown (6 blocks) and half a block off the famous Little Italy street for food and cocktails and then brunch and coffee in walking distance in the mornings too. The unit had everything you need, fully stocked kitchen and bath, shared laundry. Great mattress and pillows! Easy keypad entry. I’d stay there over and over again!"
United States
Erica S.
The price is ￥19,041
￥49,400 total
includes taxes & fees
Jun 8 - Jun 9
Cozy Stay by Little Italy & Wooster Street
Interior

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.
New Railside Residents
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
The price is ￥24,642
￥48,619 total
includes taxes & fees
Jul 1 - Jul 2
Private Apartment in Southbury 104
Interior

The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Host had great communication. The unit was clean, cozy and comfortable. Will book again when in the area."
United States
Tod B.
The price is ￥11,041
￥40,120 total
includes taxes & fees
Jun 7 - Jun 8
The Sun Filled Cozy Creamery
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (10 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is ￥18,881
￥46,675 total
includes taxes & fees
Jun 6 - Jun 7
All New 1BR with tons of Charm
Smart TV

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.2 out of 10, Wonderful, (20 reviews)
"Easy check in Rooms were comfortably spacious "
United States
Benjamin W.
The price is ￥20,161
￥33,906 total
includes taxes & fees
Jun 7 - Jun 8
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Smart TV

The Sicilian

The Sicilian
West New Haven
9.2 out of 10, Wonderful, (15 reviews)
"Perfect spot for a quick overnight. Cozy and very nicely decorated. "
United States
Jason S.
The price is ￥15,697
￥38,454 total
includes taxes & fees
Jun 8 - Jun 9
The Sicilian
Hair dryer, towels

Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is ￥18,000
￥60,950 total
includes taxes & fees
Jun 8 - Jun 9
Art House 3 Beds Close to Warner Theater
TV

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 ￥18,881
￥46,355 total
includes taxes & fees
Jun 8 - Jun 9
Newly Remodeled with deck. Close to town center
Marina

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is ￥35,522
￥62,132 total
includes taxes & fees
Jun 29 - Jun 30
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
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

4/10 Poor
"Pretty much a road side motel, old carpet and unfriendly staff"
Sonya 1-night trip
Posted 1 hour ago
Best Western Executive Hotel Of New Haven - West Haven

Find out more about Middlebury

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

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 Waterbury City Hall and Palace Theatre.

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.