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Compare 242 Vacation Homes in Middlebury with updated reviews, rates, and availability.

Private Annex/Former Artist Studio
10.0 out of 10, Exceptional, (46)
"The owner greeted us the first night. Very pleasant and super friendly. The space is beautiful and the fact that it was once an artist's studio for me made it even more special. The nearby lake is gorgeous. We brought our dog and she was very relaxed and comfortable for the stay. I thoroughly enjoyed the property and our mini vacation! "
Private Annex/Former Artist Studio
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (23)
"Fantastic place! Beautiful views, lots of room, comfy beds, clean. There was 10 of us and it was a delight. Highly recommend it. "
Lakeview Estate - Chef's Kitchen - NYC Getaway
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (73)
"Our group of 2 couples enjoyed our week in the Hudson Valley area. We all commented on the excellent beds and pillows, the view of the lake from the house and the quiet of the neighborhood. Would stay here again."
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
10.0 out of 10, Exceptional, (46)
"The house was beautiful and a perfect place for our family to be at while visiting our daughter who is a student at Yale. We saw the sunrise over the ocean from our bedroom window. Wish we found this sooner!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Amazing Lakefront Property
9.8 out of 10, Exceptional, (23)
"Great views and a good central location for day trips 👌. "
Amazing Lakefront Property
Tranquil Litchfield Connecticut Retreat".
9.8 out of 10, Exceptional, (6)
"They obviously care very much about the place. Everything was pristine. Beds were comfortable. Location was convenient. Everything was as advertised. "
The price is AED 808
AED 1,152 total
includes taxes & fees
18 Nov - 19 Nov
Tranquil Litchfield Connecticut Retreat".
Lakefront Home, Close to Mt Southington!
10.0 out of 10, Exceptional, (13)
"Staff very much enjoyed the atmosphere after long days of work. Wonderful Ownership. Thank you so much Susan!"
Lakefront Home, Close to Mt Southington!
Cozy Modern Home
9.6 out of 10, Exceptional, (29)
"I gave the property listing all five stars because all aspects of the property were as described in the listing. The only suggestion l have for improvement of the property would be for hand railings to be installed on the wall side of the stairs to the 2nd floor, as the stairs are very steep and hard to navigate for an older person. "
Cozy Modern Home
The Goshen Glass Chalet
9.4 out of 10, Exceptional, (27)
"Wanted to visit my son in Litchfield around Halloween with my 2 teenaged granddaughters. The Goshen Glass Chalet was the perfect place for our visit. Loved every detail. "
The Goshen Glass Chalet
Charming 3BR Hilltop House, Newly Remodeled with Arcade
10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
9.6 out of 10, Exceptional, (11)
"Very nice and clean family was visiting my daughter at the University of New Haven was also very close "
The price is AED 533
AED 1,024 total
includes taxes & fees
25 Nov - 26 Nov
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
McAngel Haven: 5 mins from Yale
9.6 out of 10, Exceptional, (5)
"The house was perfect for a family of 4 and a couple! It’s a fairly quiet neighborhood so it was a good place to come back to relax each day. Parking for 2 cars was helpful and the coded entry was very easy. Nice setup and thoughtful features. Angela was very responsive and friendly! Definitely recommend!"
The price is AED 804
AED 1,944 total
includes taxes & fees
21 Nov - 22 Nov
McAngel Haven: 5 mins from Yale
Home on the sound
8.6 out of 10, Excellent, (7)
"This was a greay stay and the property was really cute and cozy. It is an upstairs portion of a duplex "
Home on the sound
Cozy 2 bedroom home located minutes from downtown
9.6 out of 10, Exceptional, (23)
"We found this house to be the perfect spot just outside downtown New Haven. We did need a car, but the location was great. We had easy access to main roads, downtown, and there was sufficient local restaurants and stores for stocking the house. The unit was as it appeared and the host was responsive and helpful when needed."
Cozy 2 bedroom home located minutes from downtown
Gather your family at this country estate
10.0 out of 10, Exceptional, (3)
"This is an older home with charm. Lots of room, and while just six of us stayed, it appears more could be accommodated with inflatable mattresses. We enjoyed sitting outside by the simple fire pit one night. I would encourage the owners to put an outside light in the back as I stumbled on the stairs twice but that’s really the only issue. We are so sorry we misplaced one of the two keys,please send us a bill for a copy if you don’t find it. Thank you!"
Gather your family at this country estate
Near Yale 8 beds Gaming Room
The price is AED 2,020
AED 4,035 total
includes taxes & fees
20 Nov - 21 Nov
Near Yale 8 beds Gaming Room
NEW-Another Fun Downtown Location 1st floor
2.0 star property
10.0 out of 10, Exceptional, (6)
"This was our second stay at this VRBO and hope to stay again on return trips to the area."
NEW-Another Fun Downtown Location 1st floor
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
2.0 star property
10.0 out of 10, Exceptional, (2)
"Amazing view amazing hot tub very relaxing "
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
10.0 out of 10, Exceptional, (105)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
Candlewood Lake Grand Waterfront Oasis: A Luxurious Family Retreat
10.0 out of 10, Exceptional, (41)
"The Hosts were extremely nice and helpful in the entire process. They answered questions and helped me understand the offering so I could book with confidence, The home is spacious and welcoming in design. Generous spaces throughout including a very nice kitchen and a basement gameroom that was very enjoyable. The outside seating areas were outstanding including a wonderful lakefront area to sit and enjoy the views. Book with confidence for a great experience. Dan and Kit "
Candlewood Lake Grand Waterfront Oasis: A Luxurious Family Retreat
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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Other property types in Middlebury

New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1964)
"It is a great Apartment-hotel and the suites have the right amenities. One critic that I have would be that there would sometimes you could smell the cigarette smoke from other neighbours blowing into the furnace. Public transportation is limited and so it's best to have a car. Staff is super helpful and accommodating. "
The price is AED 307
AED 342 total
includes taxes & fees
24 Nov - 25 Nov
New Haven Village Suites
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (73)
"Our group of 2 couples enjoyed our week in the Hudson Valley area. We all commented on the excellent beds and pillows, the view of the lake from the house and the quiet of the neighborhood. Would stay here again."
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
9.4 out of 10, Exceptional, (86)
"Perfectly adorable house that was ideal for our brief getaway. I wish we had been able to use the kayak/canoe but time was tight. The only issue was the driveway which had me holding my breath a bit but luckily we were careful and managed without incident."
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
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.