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Middlebury Holiday Rentals

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Holiday Rentals in Middlebury

Soothing 2-bedroom lower-level apartment in 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.
The price is AU$414
includes taxes & fees
20 Oct - 21 Oct
Soothing 2-bedroom lower-level apartment in Berlin
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (9)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is AU$272
includes taxes & fees
20 Oct - 21 Oct
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
The Sun Filled Cozy Creamery
8.8 out of 10, Excellent, (22)
"Nice,cozy and a reasonable rate."
United States
Rachelle B.
The price is AU$427
includes taxes & fees
20 Oct - 21 Oct
The Sun Filled Cozy Creamery
The Nest At Elm City Flats.
10.0 out of 10, Exceptional, (3)
"Nice place! Short but sweet trip. Appreciate how quick your communication was and your accommodations!"
United States
Lori K.
The price is AU$365
includes taxes & fees
21 Oct - 22 Oct
The Nest At Elm City Flats.
Once the old Schools house now a newly furnished Apartment
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.
The price is AU$430
includes taxes & fees
31 Oct - 1 Nov
Once the old Schools house now a newly furnished Apartment
Modern apartment in Westville/Yale Bowl area
10.0 out of 10, Exceptional, (32)
"We would stay here again in a heartbeat!"
United States
Denise B.
The price is AU$357
includes taxes & fees
1 Nov - 2 Nov
Modern apartment in Westville/Yale Bowl area
Angelica’s safe haven @ west haven
10.0 out of 10, Exceptional, (5)
"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 AU$525
includes taxes & fees
20 Oct - 21 Oct
Angelica’s safe haven @ west haven
All New Private and Cozy in great location
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.
The price is AU$448
includes taxes & fees
20 Oct - 21 Oct
All New Private and Cozy in great location
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
9.6 out of 10, Exceptional, (4)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is AU$425
includes taxes & fees
20 Oct - 21 Oct
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
All New 1BR with tons of Charm
9.6 out of 10, Exceptional, (4)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AU$440
includes taxes & fees
26 Oct - 27 Oct
All New 1BR with tons of Charm
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
9.8 out of 10, Exceptional, (7)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is AU$191
includes taxes & fees
26 Oct - 27 Oct
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Charming Studio| Near Yale| Downtown New Haven
8.6 out of 10, Excellent, (7)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
United States
Jason K.
The price is AU$313
includes taxes & fees
20 Oct - 21 Oct
Charming Studio| Near Yale| Downtown New Haven
Yale Casa Verde Studio
9.8 out of 10, Exceptional, (6)
"The apartment was very comfortable , clean and close to the university. "
United States
María P.
The price is AU$329
includes taxes & fees
20 Oct - 21 Oct
Yale Casa Verde Studio
Fully Furnished 1BR Apartment
10.0 out of 10, Exceptional, (1)
"This was a great place to stay in town when visiting family! Kitchen was well stocked, location was convenient, & it had everything we needed!"
United States
Jennifer L.
The price is AU$448
includes taxes & fees
20 Oct - 21 Oct
Fully Furnished 1BR Apartment
New One Bedroom Apartment Centrally Located in Southbury
9.8 out of 10, Exceptional, (11)
"Excellent place in an excellent location. Charles is a wonderful host. Will be staying there again. "
United States
Robert
The price is AU$193
includes taxes & fees
28 Oct - 29 Oct
New One Bedroom Apartment Centrally Located in Southbury
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
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.
The price is AU$341
includes taxes & fees
20 Oct - 21 Oct
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
Downtown loft apartment in the heart of downtown New Haven.
9.0 out of 10, Wonderful, (2)
"Great for a quick stay (we were here 10 hours). The water in the shower didn't warm at all, even after running it for 10 minutes it was still freezing. Area was great and I appreciated the thorough instructions to get in the apartment. "
United States
Madeline S.
The price is AU$272
includes taxes & fees
20 Oct - 21 Oct
Downtown loft apartment in the heart of downtown New Haven.
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
2.0 star property
8.0 out of 10, Very good, (1)
"Outstanding location and room. Please recheck the structure of the outdoor stairs. There are no support pullers from the top landing to the ground level. They’re attached directly to the home but has gaps by the windows. The stares are very slippery when wet and the arm rails are below waist level. Unfinished wood rails make splinters a thing. Super clean, quiet and relaxing. Would reserve again if we come back to the area. Thank you so much for all the support. "
United States
Pat D.
The price is AU$202
includes taxes & fees
20 Oct - 21 Oct
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
Cozy Haven Near Yale|Wooster Square|Washer/Dryer
8.0 out of 10, Very good, (2)
"Lovely place to stay- clean, amazing and kind host. Ideal location near Yale but quiet and safe. Onsite parking was great. Will def try to stay here again!"
United States
Mayra O.
Cozy Haven Near Yale|Wooster Square|Washer/Dryer
Westville Nest•EastRock Escape• 2BR •NearYale•Wifi
The price is AU$355
includes taxes & fees
20 Oct - 21 Oct
Westville Nest•EastRock Escape• 2BR •NearYale•Wifi
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

Everything you need to know about Middlebury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middlebury holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlebury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlebury holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middlebury rentals

At Expedia, we put the best Middlebury holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Quassy Amusement Park, or you can select a more secluded option if you're looking for a relaxing stay. Middlebury is known for its parks.

What are some of the best holiday rentals that Middlebury has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Middlebury offers a fireplace, a patio and a BBQ 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 that 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 wider area, you’ll find Palace Theatre and Brass Mill Center.

What’s a holiday rental in Middlebury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlebury. Holiday rentals feature extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip.