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Search Vacation Homes in Middlebury

Compare 263 Vacation Homes in Middlebury with updated reviews, rates, and availability.

Updated ranch Home 4 minutes from the beach on a quiet end street.
6.0 out of 10, (1)
"Family of 5 (2 adults, 3 teens) stayed for long weekend. Friendly and fairly quick communication with Fabian was appreciated. House is approx 1 to 1.5 miles to Long Island Sound and beach. Nice and quiet neighborhood. The place was clean with exception of downstairs which had some of the owner's personal belongings strewn about. The biggest disappoint was no hot water or heat for most of the stay. Fabian offered hot showers at another nearby location and brought in a space heater which was...
Updated ranch Home 4 minutes from the beach on a quiet end street.
Lakeside luxury: beautiful, relaxing 4 bedroom home
10.0 out of 10, Exceptional, (2)
"We stayed at the house with our adult children and grandchild. The house was very clean. The linens, towels were of high quality and clean, and the kitchen was very functional with new cooking and kitchen utensils, pots and pans. It had hardwood floors on main level and the house was not cluttered at all. The view from the living room and deck of the lake was so beautiful and a stress release for sure. The backyard was roomy and well maintained. The neighborhood was quiet. The owner/manager was...
Lakeside luxury: beautiful, relaxing 4 bedroom home
Gorgeous NEW Candlewood Lake 4BR 2BA Direct Waterfront Home +Dock ~JUNE SPECIAL!
Gorgeous NEW Candlewood Lake 4BR 2BA Direct Waterfront Home +Dock ~JUNE SPECIAL!
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Charming 1870 cape cottage in Litchfield
10.0 out of 10, Exceptional, (21)
"The cottage house had a warm, welcoming vibe to it. It was very well maintained. The grounds were beautiful. The home had everything available that you could possibly want. It was very cozy. We had relatives from Italy with us and they absolutely loved it. I would definitely go back and I highly recommend it. Congratulations to the owners, because they have done a wonderful job with it."
Charming 1870 cape cottage in Litchfield
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, (17)
"Gorgeous, as advertised!"
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (59)
"We had a lovely weekend stay for a quick family get-away. The main kitchen and living area has spectacular views onto the lake as does the deck where we spent most of our time. The lake is just across the very quiet street. The kitchen is incredibly well stocked, the host super responsive and the rooms very comfortable. We did not use the well equipped basement work-out and additional TV space but it looked great. Easy to get to grocery store, hikes, local attractions but honestly we just loved...
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, (17)
"The property is lovely and well prepared for guests. The location is wonderful. One of our highlights was watching a bald eagle soar over the lake."
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Amazing Lakefront Property
10.0 out of 10, Exceptional, (15)
"This was my second go round staying at this property. My family and I enjoyed it the first time. More so the second time with the upgrades. Being familiar with the area was a great help. This time we went in the lake and enjoyed ourselves. We are looking forward to returning back again. Thank you Raymond for letting us stay at your property. Richard and Joanne"
Amazing Lakefront Property
The Long View of Candlewood Lake
9.8 out of 10, Exceptional, (8)
"We were In the area for Kent Graduation . Wish we had more time to spend at the house . Perfect area by lake. Nice setup . Great neighbors . The host was very responsive and so accommodating with our busy schedule and short stay. We’ll be back for a longer stay to enjoy the property, house and lake."
The Long View of Candlewood Lake
Cozy Modern Home
9.6 out of 10, Exceptional, (26)
"Very nice place, stay there for a couple of nights for a get together, plenty of room. Only problem was some of the cleaning supplies where locked away where we couldn’t access it so we had to bring a mop and other supplies."
Cozy Modern Home
McAngel Haven: 5 mins from Yale
9.0 out of 10, Wonderful, (2)
"The location was good for our needs and the place well maintained. There were scent devices in many outlets and two of our guests are allergic. We had to unplug them and air out the home. It would be good to alert guests to those devices and allow them to choose to have them not present."
The price is $219
$529 total
includes taxes & fees
Jun 9 - Jun 10
McAngel Haven: 5 mins from Yale
Private Annex/Former Artist Studio
9.8 out of 10, Exceptional, (39)
"This charming 2-bedroom New Preston apartment was the perfect escape! Cozy rooms welcomed us with peace and comfort, melting away city stress. Host Melanie's warm smile and delicious homemade cookies added a personal touch that made our stay truly heartwarming. Reconnecting with nature was easy - breathtaking scenery, quiet streets, and a nearby lake offered peaceful beauty. This wasn't just a place to stay, it was an experience we'll treasure. Highly recommend! ⭐⭐⭐⭐⭐ P.S. too bad I forgot...
Private Annex/Former Artist Studio
Litchfield County Getaway
10.0 out of 10, Exceptional, (35)
"Very nicely renovated house. Clean and comfortable. Well equipped kitchen. Large comfy living and dining room. Very responsive hosts. Only suggestion would be to provide a few more hooks in the bathrooms for guests to hang personal things (night clothes, used towels, etc.). I would highly recommended this place."
Litchfield County Getaway
Near Yale 8 beds Gaming Room
Near Yale 8 beds Gaming Room
lakefront estate
3.8 out of 10, (8)
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (18)
"Beautiful, spacious property with all the amenities we needed and more. I would recommend and we will certainly return!"
The price is $470
$961 total
includes taxes & fees
Jun 13 - Jun 14
Lakeview Estate - Chef's Kitchen - NYC Getaway
Beachside Retreat
9.4 out of 10, Exceptional, (3)
"Old world charm meets modern amenities, beach views are calming and relaxing. Exceptional communication with host."
Beachside Retreat
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
10.0 out of 10, Exceptional, (6)
"Great property, very clean and host was quick to reply. We were impressed with the amenities available (most places don’t have detergent, etc) and the view was amazing! We didn’t have time to go to the dock but it looked very nice! Wish we had time to stay longer. We will definitely try to stay there again for our next family event"
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
Traveling Nurse or Business Professional
10.0 out of 10, Exceptional, (7)
"The neighborhood was clean, upscale, and beautifully kept. It came with Candlewood Beach access. The second story suite was gorgeous, clean, and well apportioned. The bed was comfortable. The whole house was well maintained and a wonderful,"homey" feel to it. The Hostess was friendly, cheerful, and very accommodating. The house is on the hillside leading to Lake Candlewood. As can be imagined, the views from the windows were outstanding."
Traveling Nurse or Business Professional
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
10.0 out of 10, Exceptional, (33)
"Property was as pictured. Gorgeous home on the lake. So well appointed. Everything you could possibly need. Host was super responsive. Could not ask for more. Already planning for next year."
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
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See all available properties in Middlebury
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.

Other property types in Middlebury

New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1842)
"Comfortable beds and clean for the most part. Rooms are good size. More like a studio apartment. Will stay again sometime 👍 👍 ✌️. "
The price is $95
$109 total
includes taxes & fees
Jul 7 - Jul 8
New Haven Village Suites
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (59)
"We had a lovely weekend stay for a quick family get-away. The main kitchen and living area has spectacular views onto the lake as does the deck where we spent most of our time. The lake is just across the very quiet street. The kitchen is incredibly well stocked, the host super responsive and the rooms very comfortable. We did not use the well equipped basement work-out and additional TV space but it looked great. Easy to get to grocery store, hikes, local attractions but honestly we just loved...
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, (75)
"We had such an awesome stay! Check in process was easy! Amazing scenery amazing adventure we had with our two furr babies!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from 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.

Middlebury Vacation Homes information

Number of reviews
313
Accommodation
263 Vacation Homes
Lowest Price
$219
Highest Price
$470

Recent reviews of Middlebury hotels
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