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Middlebury Vacation Rentals

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Nov 22 - Nov 23
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Vacation Rentals in Middlebury

Interior
The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery

Plainville
8.8 out of 10, Excellent, (24)
"Nice,cozy and a reasonable rate."
United States
Rachelle B.
$257 nightly
The price is $275
Nov 23 - Nov 24
Total with taxes and fees
The Sun Filled Cozy Creamery
Outdoor dining
Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin

Berlin
10.0 out of 10, Exceptional, (1)
"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.
$246 nightly
The price is $278
Nov 23 - Nov 24
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
Fridge, microwave, oven, stovetop
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, (11)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
$145 nightly
The price is $163
Nov 23 - Nov 24
Total with taxes and fees
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
9.6 out of 10, Exceptional, (10)
"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.
$247 nightly
The price is $257
Dec 1 - Dec 2
Total with taxes and fees
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

Wallingford Center
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$271 nightly
The price is $288
Nov 23 - Nov 24
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
TV
All New Private and Cozy in great location

All New Private and Cozy in great location

Wallingford
8.8 out of 10, Excellent, (6)
"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.
$271 nightly
The price is $288
Nov 26 - Nov 27
Total with taxes and fees
All New Private and Cozy in great location
Fridge, microwave, oven, stovetop
All New 1BR with tons of Charm

All New 1BR with tons of Charm

Wallingford Center
9.8 out of 10, Exceptional, (6)
"I highly recommend this property!! We were in town for a wedding celebration, and it proved perfect. The property is completely updated, well-appointed and clean. The property is centrally located and close to restaurants, shops and grocery markets. Karl was a great host and communicated with us throughout our stay. I highly recommend!!"
United States
Francis S.
$271 nightly
The price is $288
Nov 23 - Nov 24
Total with taxes and fees
All New 1BR with tons of Charm
1 bedroom, WiFi, bed sheets
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

2.0 star property
West New Haven
9.0 out of 10, Wonderful, (2)
"Great communication and easy check in, would recommend "
United States
Ethan R.
$115 nightly
The price is $129
Nov 23 - Nov 24
Total with taxes and fees
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
Private kitchen
Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking

West New Haven
10.0 out of 10, Exceptional, (1)
"The unit was very clean and in a walkable neighborhood. Laundry was shared but easy to use in basement. The parking is not included. There's lots of safe street parking. "
United States
Thomas B.
$249 nightly
The price is $249
Nov 25 - Nov 26
Total with taxes and fees
Westville Stay • 2BR • Near Yale • Free Parking
Interior
The Nest At Elm City Flats.

The Nest At Elm City Flats.

West New Haven
9.4 out of 10, Exceptional, (6)
"The house itself was very nice and in excellent shape. Almost everything in the house seemed new. Kudos! The biggest negative was the neighborhood, which was trashy."
United States
Keith C.
$210 nightly
The price is $238
Nov 23 - Nov 24
Total with taxes and fees
The Nest At Elm City Flats.
Interior
#31 - Downtown Terryville- 1 Br

#31 - Downtown Terryville- 1 Br

Plymouth
10.0 out of 10, Exceptional, (1)
"In convenient safe area. Os is easy to contact"
United States
Gina P.
$237 nightly
The price is $254
Nov 23 - Nov 24
Total with taxes and fees
#31 - Downtown Terryville- 1 Br
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.

Watertown
9.8 out of 10, Exceptional, (7)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
$109 nightly
The price is $122
Nov 23 - Nov 24
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior
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)
"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.
$232 nightly
The price is $276
Nov 23 - Nov 24
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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
10.0 out of 10, Exceptional, (1)
"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.
$212 nightly
The price is $220
Nov 24 - Nov 25
Total with taxes and fees
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
Interior
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)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
$174 nightly
The price is $197
Nov 23 - Nov 24
Total with taxes and fees
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Interior
DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!

DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!

Downtown New Haven
10.0 out of 10, Exceptional, (1)
"We stayed here on our last night of a month long vacation. After a month of travel, you want convenience and comfort. This place offered us a fantastic last night away from home. It’s right across the street from the train station, easy walking to shops and dining, and just an overall beautiful apartment. It was clean and cozy with immaculate decorating. The entry and exit were easy. Accommodations were superior. Don’t forget to grab pizza!! "
United States
Daniel L.
$302 nightly
The price is $342
Nov 23 - Nov 24
Total with taxes and fees
DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!
Fridge, microwave, oven, stovetop
#23 *COMFORT & LUXURY* 3 BR/2 BA House

#23 *COMFORT & LUXURY* 3 BR/2 BA House

Southington
9.8 out of 10, Exceptional, (8)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
#23 *COMFORT & LUXURY* 3 BR/2 BA House
Exterior
New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury

Southbury
9.8 out of 10, Exceptional, (17)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
$115 nightly
The price is $129
Nov 23 - Nov 24
Total with taxes and fees
New One Bedroom Apartment Centrally Located in Southbury
1 bedroom, desk, iron/ironing board, WiFi
One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven

Dwight
10.0 out of 10, Exceptional, (1)
"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.
$200 nightly
The price is $226
Nov 25 - Nov 26
Total with taxes and fees
One bedroom apartment in United States of America, New Haven
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Private Apartment in Berlin

2.0 star property
Berlin
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
$279 nightly
The price is $316
Nov 23 - Nov 24
Total with taxes and fees
Private Apartment in Berlin
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

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

10/10 Excellent
"Very nice and clean!"
Victor 3-night trip
Posted 2 days ago
Cambria Hotel New Haven University Area

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 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?

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit: This vacation home rental near Middlebury is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, an arcade game room, and a hot tub so you can immerse yourself in your vacation.

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 Hollow Park 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.