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Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Middlebury vacation rentals

Interior
Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking
West New Haven
10.0 out of 10, Exceptional, (3 reviews)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
The price is ￥11,282
￥35,100 total
includes taxes & fees
Jan 13 - Jan 14
Westville Stay • 2BR • Near Yale • Free Parking
Exterior
Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (21 reviews)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is ￥14,416
￥19,712 total
includes taxes & fees
Feb 9 - Feb 10
Cozy One Bedroom Apartment Centrally Located in Southbury
Smart TV
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

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, (14 reviews)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is ￥13,274
￥25,620 total
includes taxes & fees
Jan 14 - Jan 15
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Interior
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

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
8.6 out of 10, Excellent, (10 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is ￥13,946
￥19,172 total
includes taxes & fees
Feb 9 - Feb 10
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior
Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
Downtown New Haven
9.0 out of 10, Wonderful, (12 reviews)
"Great location, exactly as advertised. The shades are somewhat translucent, so a bit bright at night, but wore a mask and it was fine. "
United States
Scott B.
The price is ￥9,885
￥27,458 total
includes taxes & fees
Jan 12 - Jan 13
Charming Studio| Near Yale| Downtown New Haven
Fridge, microwave, oven, stovetop
One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven
Dwight
9.4 out of 10, Exceptional, (3 reviews)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
The price is ￥14,887
￥32,281 total
includes taxes & fees
Feb 9 - Feb 10
One bedroom apartment in United States of America, New Haven
TV
Newly Remodeled with deck. Close to town center

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 ￥18,021
￥44,542 total
includes taxes & fees
Feb 9 - Feb 10
Newly Remodeled with deck. Close to town center
Interior
All New Studio apartment in center of town

All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
The price is ￥18,021
￥45,169 total
includes taxes & fees
Jan 12 - Jan 13
All New Studio apartment in center of town
Cookware/dishes/utensils
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

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, (11 reviews)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
The price is ￥16,945
￥44,070 total
includes taxes & fees
Jan 12 - Jan 13
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
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

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 ￥18,044
￥45,227 total
includes taxes & fees
Jan 10 - Jan 11
Once the old Schools house now a newly furnished Apartment
Interior
Private Apartment in Berlin

Private Apartment in Berlin

Private Apartment in Berlin
2.0 star property
Berlin
9.2 out of 10, Wonderful, (5 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 ￥15,847
￥46,231 total
includes taxes & fees
Jan 11 - Jan 12
Private Apartment in Berlin
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Torrington
9.6 out of 10, Exceptional, (4 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is ￥15,321
￥55,236 total
includes taxes & fees
Jan 13 - Jan 14
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Dining
Spacious 2 Bedroom apartment close to Yale Bowl

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, (69 reviews)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
The price is ￥20,371
￥35,571 total
includes taxes & fees
Feb 9 - Feb 10
Spacious 2 Bedroom apartment close to Yale Bowl
Desk, iron/ironing board, WiFi, bed sheets
Yale Casa Verde Studio

Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.6 out of 10, Exceptional, (8 reviews)
"Had a great stay!"
United States
Jeffrey C.
The price is ￥14,887
￥31,967 total
includes taxes & fees
Feb 9 - Feb 10
Yale Casa Verde Studio
Interior
The Nest At Elm City Flats.

The Nest At Elm City Flats.

The Nest At Elm City Flats.
West New Haven
9.4 out of 10, Exceptional, (6 reviews)
"We had a great stay at this apartment. You do have to go up three flight of stairs but thankfully we were able to climb them. "
United States
Joan S.
The price is ￥13,980
￥37,298 total
includes taxes & fees
Jan 11 - Jan 12
The Nest At Elm City Flats.
Interior
Private Apartment in Southbury 101

Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
The price is ￥16,631
￥43,367 total
includes taxes & fees
Jan 19 - Jan 20
Private Apartment in Southbury 101
Apartment (2 Bedrooms) | Interior
2 Mi to Beach, Shared Yard Space: West Haven Apt!

2 Mi to Beach, Shared Yard Space: West Haven Apt!

2 Mi to Beach, Shared Yard Space: West Haven Apt!
3.0 star property
West Haven
The price is ￥21,495
￥56,173 total
includes taxes & fees
Jan 11 - Jan 12
2 Mi to Beach, Shared Yard Space: West Haven Apt!
Exterior
Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is ￥20,475
￥49,710 total
includes taxes & fees
Jan 10 - Jan 11
Angelica’s safe haven @ west haven
Terrace/patio
Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
Berlin
10.0 out of 10, Exceptional, (1 review)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is ￥19,205
￥50,288 total
includes taxes & fees
Jan 12 - Jan 13
Soothing 2-bedroom lower-level apartment in Berlin
1 bedroom, iron/ironing board, free WiFi, bed sheets
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Shelton
9.0 out of 10, Wonderful, (2 reviews)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is ￥18,804
￥30,682 total
includes taxes & fees
Feb 9 - Feb 10
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
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

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:

  • View our selection of featured holiday rentals in Middlebury
  • Use the map to find apartments and other holiday homes in the Middlebury neighbourhood you prefer
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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.