Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Middlebury vacation rentals

2 bedrooms, WiFi, bed sheets

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (6 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is ￥14,563
￥38,164 total
includes taxes & fees
Apr 21 - Apr 22
Private Apartment in Berlin
Private kitchen

Cozy Room in charming New Haven near Yale/Hospitals!

Cozy Room in charming New Haven near Yale/Hospitals!
The Hill
9.4 out of 10, Exceptional, (3 reviews)
"Very nice house and very clean I really love it "
United States
Peterson
The price is ￥11,422
￥24,518 total
includes taxes & fees
May 1 - May 2
Cozy Room in charming New Haven near Yale/Hospitals!
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
The price is ￥15,071
￥32,363 total
includes taxes & fees
Apr 21 - Apr 22
One bedroom in United States of America, New Haven
Smart TV

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.4 out of 10, Exceptional, (17 reviews)
"Easy check in Rooms were comfortably spacious "
United States
Benjamin W.
The price is ￥16,276
￥29,188 total
includes taxes & fees
Apr 28 - Apr 29
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cookware/dishes/utensils

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.8 out of 10, Exceptional, (14 reviews)
"wonderful stay - great apartment and location and communication!"
United States
Anonymous traveler
The price is ￥17,926
￥45,122 total
includes taxes & fees
Apr 27 - Apr 28
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
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, (70 reviews)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
The price is ￥20,623
￥36,011 total
includes taxes & fees
Apr 21 - Apr 22
Spacious 2 Bedroom apartment close to Yale Bowl
Exterior

GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds

GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds
East Rock
10.0 out of 10, Exceptional, (4 reviews)
"Great place - wish we had more than one night. "
United States
Steri-Clean N.
The price is ￥25,858
￥65,712 total
includes taxes & fees
Apr 21 - Apr 22
GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds
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 ￥23,003
￥53,541 total
includes taxes & fees
Apr 21 - Apr 22
Angelica’s safe haven @ west haven
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 ￥18,720
￥46,276 total
includes taxes & fees
May 1 - May 2
Once the old Schools house now a newly furnished Apartment
Dining

Stocked home close to Yale, in Heart of New Haven

Stocked home close to Yale, in Heart of New Haven
Mill River
9.2 out of 10, Wonderful, (20 reviews)
"Great value very close to university. "
United States
Lawrence
The price is ￥19,989
￥35,099 total
includes taxes & fees
Apr 21 - Apr 22
Stocked home close to Yale, in Heart of New Haven
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is ￥18,720
￥46,276 total
includes taxes & fees
May 1 - May 2
All New 1BR with tons of Charm
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 ￥17,847
￥39,205 total
includes taxes & fees
Apr 21 - Apr 22
Spacious Bohemian Nook
Smart TV

The Sicilian

The Sicilian
West New Haven
9.4 out of 10, Exceptional, (13 reviews)
"Cozy space"
United States
Matt W.
The price is ￥15,563
￥37,490 total
includes taxes & fees
Apr 21 - Apr 22
The Sicilian
Desk, iron/ironing board, WiFi, bed sheets

Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.6 out of 10, Exceptional, (10 reviews)
"A lovely space and very smooth checkin and checkout process. "
United States
Daphne A.
The price is ￥15,071
￥32,363 total
includes taxes & fees
Apr 22 - Apr 23
Yale Casa Verde Studio
Exterior

Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.0 out of 10, Wonderful, (14 reviews)
"Conveniently located and nice, practically appointed stay for a business trip to work with a collaborator in town."
United States
Jeremy Y.
The price is ￥18,244
￥39,113 total
includes taxes & fees
Apr 21 - Apr 22
Bright Downtown Studio near Yale & East Rock!
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 ￥18,720
￥46,276 total
includes taxes & fees
May 1 - May 2
All new 1BR apartment with all the features you are looking for
Marina

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
7.6 out of 10, Good, (5 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is ￥22,210
￥40,930 total
includes taxes & fees
Apr 21 - Apr 22
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Dining

Great 3 Bedroom close to downtown and Yale!

Great 3 Bedroom close to downtown and Yale!
Mill River
8.2 out of 10, Very Good, (23 reviews)
"Very spacious. We enjoyed our stay here. "
United States
Jennifer F.
The price is ￥21,202
￥36,677 total
includes taxes & fees
Apr 21 - Apr 22
Great 3 Bedroom close to downtown and Yale!
Interior

Modern Studio Retreat

Modern Studio Retreat
Dwight
The price is ￥27,048
￥42,568 total
includes taxes & fees
May 19 - May 20
Modern Studio Retreat
Interior

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
The price is ￥15,705
￥21,234 total
includes taxes & fees
Apr 21 - Apr 22
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
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

La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

10/10 Excellent
"Everything was great for a one night stay"
Tyler 1-night trip
Posted 3 hours ago
La Quinta Inn & Suites by Wyndham New Haven

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:

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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 Palace Theatre and Holy Land USA.

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.