Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Middlebury vacation rentals

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, (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.
$230 nightly
The price is $238
Feb 4 - Feb 5
Total with taxes and fees
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Exterior

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Torrington
9.2 out of 10, Wonderful, (5 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.
$288 nightly
The price is $329
Feb 3 - Feb 4
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
2 bedrooms, WiFi, bed sheets

Private Apartment in Berlin

Private Apartment in Berlin
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.
$261 nightly
The price is $296
Feb 3 - Feb 4
Total with taxes and fees
Private Apartment in Berlin
Apartment (2 Bedrooms) | Interior

Luxe Living! Apt 1 Mi to West Haven Medical Center

Luxe Living! Apt 1 Mi to West Haven Medical Center
3.0 star property
West Haven
$311 nightly
The price is $358
Feb 3 - Feb 4
Total with taxes and fees
Luxe Living! Apt 1 Mi to West Haven Medical Center
Exterior

Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.0 out of 10, Wonderful, (13 reviews)
"Everything was great and just as charming as the photo indicated. "
United States
Nancy F.
$207 nightly
The price is $225
Feb 3 - Feb 4
Total with taxes and fees
Bright Downtown Studio near Yale & East Rock!
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.
$271 nightly
The price is $288
Feb 3 - Feb 4
Total with taxes and fees
All New 1BR with tons of Charm
1 bedroom, iron/ironing board, free WiFi, bed sheets

#2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*
Plainville
9.0 out of 10, Wonderful, (2 reviews)
"I try to come up to Connecticut at least once a year if possible and this really worked out perfect for me first floor no steps easy to bring luggage in very comfortable. Would definitely come back and stay there again."
United States
Rodney L.
$192 nightly
The price is $207
Feb 8 - Feb 9
Total with taxes and fees
#2 *Beautiful 1 BR Apartment - Central CT*
TV

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.
$271 nightly
The price is $288
Feb 3 - Feb 4
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Fridge, microwave, oven, stovetop

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.
$271 nightly
The price is $288
Feb 3 - Feb 4
Total with taxes and fees
All New Studio apartment in center of town
Interior

The Nest At Elm City Flats.

The Nest At Elm City Flats.
West New Haven
9.6 out of 10, Exceptional, (7 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.
$205 nightly
The price is $233
Feb 5 - Feb 6
Total with taxes and fees
The Nest At Elm City Flats.
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
8.6 out of 10, Excellent, (10 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
$116 nightly
The price is $130
Feb 6 - Feb 7
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Fridge, microwave, oven, stovetop

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (1 review)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
$448 nightly
The price is $508
Feb 3 - Feb 4
Total with taxes and fees
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
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, (15 reviews)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
$149 nightly
The price is $168
Feb 18 - Feb 19
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
3 bedrooms, iron/ironing board, WiFi, bed sheets

Sunshine Central | Yale | 3BR | Prking | Wshr/Dryr

Sunshine Central | Yale | 3BR | Prking | Wshr/Dryr
East Rock
9.0 out of 10, Wonderful, (10 reviews)
"Great 4 day visit to New Haven. We enjoyed the neighborhood and proximity to Yale."
United States
Todd L.
$266 nightly
The price is $278
Feb 4 - Feb 5
Total with taxes and fees
Sunshine Central | Yale | 3BR | Prking | Wshr/Dryr
Desk, iron/ironing board, WiFi, bed sheets

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.
$182 nightly
The price is $206
Feb 3 - Feb 4
Total with taxes and fees
Yale Casa Verde Studio
Terrace/patio

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.
$281 nightly
The price is $317
Feb 3 - Feb 4
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
Fridge, microwave, oven, stovetop

One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven
Dwight
8.6 out of 10, Excellent, (4 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.
$182 nightly
The price is $206
Feb 3 - Feb 4
Total with taxes and fees
One bedroom apartment in United States of America, New Haven
Exterior

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
$307 nightly
The price is $348
Feb 3 - Feb 4
Total with taxes and fees
Angelica’s safe haven @ west haven
Dining

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
New Britain
7.6 out of 10, Good, (7 reviews)
" Not bad for the price "
United States
Audrey L.
$329 nightly
The price is $372
Feb 3 - Feb 4
Total with taxes and fees
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
Fridge, microwave, oven, stovetop

#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.
$360 nightly
The price is $382
Feb 3 - Feb 4
Total with taxes and fees
#27- Luxury Collection
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

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Room was a safe haven during a bad winter storm. The front desk attendant - I believe his name was Suvar was incredibly kind and accommodating - let us know the only place that was open and where we could get a hot meal after a 12 hour shift in the hospital."
Molly 1-night trip
Posted 3 days ago
New Haven Hotel

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 $126 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 Glebe House Museum and The Gertrude Jekyll Garden and Union Station Clocktower.

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.