Middlebury Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Middlebury holiday rentals

Interior

Apartment in West New Haven

Westville Stay • 2BR • Near Yale • Free Parking
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 HK$624
HK$1,832 total
includes taxes & fees
20 Jan - 21 Jan
Westville Stay • 2BR • Near Yale • Free Parking
Smart TV

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
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.
The price is HK$660
HK$1,273 total
includes taxes & fees
20 Jan - 21 Jan
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cookware/dishes/utensils

Apartment in East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale 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 HK$803
HK$2,155 total
includes taxes & fees
20 Jan - 21 Jan
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Exterior

Apartment in Downtown New Haven

Charming Studio| Near Yale| 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 HK$530
HK$1,411 total
includes taxes & fees
26 Jan - 27 Jan
Charming Studio| Near Yale| Downtown New Haven
Fridge, microwave, oven, stovetop

Apartment in Dwight

One bedroom apartment in United States of America, New Haven
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 HK$741
HK$1,591 total
includes taxes & fees
19 Jan - 20 Jan
One bedroom apartment in United States of America, New Haven
Exterior

Apartment in Torrington

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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 HK$761
HK$2,737 total
includes taxes & fees
8 Feb - 9 Feb
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Interior

Apartment in Watertown

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
8.6 out of 10, Excellent, (10 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$694
HK$954 total
includes taxes & fees
19 Jan - 20 Jan
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Fridge, microwave, oven, stovetop

Apartment in Southbury

Private Apartment in Southbury 103
10.0 out of 10, Exceptional, (2 reviews)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
The price is HK$710
HK$1,997 total
includes taxes & fees
18 Jan - 19 Jan
Private Apartment in Southbury 103
Fridge, microwave, oven, stovetop

Holiday Home in Berlin

Private Apartment in Berlin
2.0 star property
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 HK$788
HK$2,297 total
includes taxes & fees
18 Jan - 19 Jan
Private Apartment in Berlin
Exterior

Apartment in Southbury

Cozy One Bedroom Apartment Centrally Located in 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 HK$717
HK$981 total
includes taxes & fees
19 Jan - 20 Jan
Cozy One Bedroom Apartment Centrally Located in Southbury
Exterior

Apartment in West Haven

Angelica’s safe 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 HK$1,131
HK$2,709 total
includes taxes & fees
20 Jan - 21 Jan
Angelica’s safe haven @ west haven
Interior

Apartment in Downtown New Haven

DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!
10.0 out of 10, Exceptional, (2 reviews)
"This property was great! Good location and loved the design of the place. I wish I could’ve stayed longer."
United States
Lucas C.
The price is HK$936
HK$2,710 total
includes taxes & fees
19 Jan - 20 Jan
DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!
1 bedroom, iron/ironing board, WiFi, bed sheets

Holiday Home in Wallingford Center

Once the old Schools house now a newly furnished Apartment
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 HK$897
HK$2,185 total
includes taxes & fees
17 Feb - 18 Feb
Once the old Schools house now a newly furnished Apartment
Interior

Apartment in Southbury

Private Apartment in Southbury 101
9.4 out of 10, Exceptional, (6 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
The price is HK$826
HK$2,155 total
includes taxes & fees
1 Feb - 2 Feb
Private Apartment in Southbury 101
Living area

Apartment in Mill River

Wooster Gem - Walk to Pizza & Yale! - FREE Parking and Laundry
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive. I would recommend Vrbo as well as this host for future stays."
United States
Larmeka A.
The price is HK$716
HK$2,702 total
includes taxes & fees
18 Jan - 19 Jan
Wooster Gem - Walk to Pizza & Yale! - FREE Parking and Laundry
Interior

Apartment in West New Haven

The Nest At Elm City Flats.
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 HK$695
HK$1,822 total
includes taxes & fees
19 Jan - 20 Jan
The Nest At Elm City Flats.
Interior

Apartment in West Haven

Luxe Living! Apt 1 Mi to West Haven Medical Center
3.0 star property
The price is HK$1,068
HK$2,791 total
includes taxes & fees
25 Jan - 26 Jan
Luxe Living! Apt 1 Mi to West Haven Medical Center
Fridge, microwave, oven, stovetop

Holiday Home in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in 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.
The price is HK$680
HK$3,853 total
includes taxes & fees
25 Jan - 26 Jan
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Exterior

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is HK$897
HK$2,247 total
includes taxes & fees
18 Jan - 19 Jan
All New 1BR with tons of Charm
Terrace/patio

Apartment in Berlin

Soothing 2-bedroom lower-level apartment in 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 HK$968
HK$2,515 total
includes taxes & fees
19 Jan - 20 Jan
Soothing 2-bedroom lower-level 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

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Friendly staff, great location. Cheers!"
Robert 1-night trip
Posted 2 days ago
New Haven Hotel

Find out more about Middlebury

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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 Union Station Clocktower and Waterbury City Hall.

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.