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Compare 280 Vacation Homes in Middlebury with updated reviews, rates, and availability.

Incredible Family Getaway Home With Boat Dock

10.0 out of 10, Exceptional, (134)
"Wonderful home with a great view. Would love to stay here again!"
Incredible Family Getaway Home With Boat Dock

Cozy Private Bedroom with Own Entrance - No Shower

10.0 out of 10, Exceptional, (3)
"This place is a nice, cozy little getaway. Great location!! Host has thought of every little accoutrement one might need when you're away from home, everything from hand lotion to a French press!! This was my second stay here, definitely won't be my last!! Love it!"
The price is AED 294
AED 448 total
includes taxes & fees
18 Apr - 19 Apr
Cozy Private Bedroom with Own Entrance - No Shower

Moose Lodge - Rustic and Cozy

9.8 out of 10, Exceptional, (50)
"I had a great stay at the Moose Lodge. The host was very responsive and accommodating. The house was clean and neat and close to town. "
Moose Lodge - Rustic and Cozy

Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!

10.0 out of 10, Exceptional, (178)
"We loved the spectacular views and the game room. Highly recommend for a couples getaway or relaxing stay. "
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!

Classic Vermont Farmhouse near Sugarbush Resort

9.8 out of 10, Exceptional, (34)
"We had a wonderful stay at this property. Location was perfect, close to skiing, restaurants, and a grocery store. Accommodations were perfect for two families with kids. We enjoyed the fireplace and the cozy family room the best. Lots of options on the tv as well. Communication with the management company was very fast, especially after we received 2 feet of snow! The plows came promptly and we had absolutely no issues. Would stay there again!"
Classic Vermont Farmhouse near Sugarbush Resort

Ski home in the woods with a private hot tub & mountain views

9.8 out of 10, Exceptional, (43)
"Great home with 4 levels for 4 bedrooms and 3 bathroom. Wonderful living room area for gathering and games (well stocked!) Great kitchen with all we needed to prepare meals for our crowd . Heat lights in bathrooms were a bonus. Gorgeous view of the mountains - quick access to ski areas and yummy local restaurantsIssue with housekeeping / management not having home ready for our arrival but was sorted to our satisfaction - hopefully just a one-off issue for this wonderful property. Recommend 4WD...
Ski home in the woods with a private hot tub & mountain views

Beautiful lake house on Lake Champlain!

9.8 out of 10, Exceptional, (95)
"Beautiful lake views on this lakefront property. Clean, well appointed and great communication with property manager. Would definitely return- thank you for a lovely visit!"
Beautiful lake house on Lake Champlain!

FiddleHead Lane-Near Killington, Fireplace, Grill

10.0 out of 10, Exceptional, (3)
"We came up to Killington for a weekend of skiing and to enjoy all that the mountain has to offer. The house was perfect for our group. It was clean and comfortable. It had everything we needed and ample sleeping space. It was close enough to the mountain to get there quickly. The owners were extremely accommodating and always responded to any questions we had. They made us feel at home. We would definitely stay here again. "
The price is AED 496
AED 2,172 total
includes taxes & fees
1 Apr - 2 Apr
FiddleHead Lane-Near Killington, Fireplace, Grill

Modern farmhouse in classic VT orchard setting - stunning sunsets & location

2.0 star property
10.0 out of 10, Exceptional, (5)
"We stayed here over Thanksgiving break with our two college children. It was a few hours from Boston and a great location in the country overlooking a picturesque valley. The location was great for day trips exploring Vermont. The high quality furniture, rugs, and mattresses made it feel like you were visiting wealthy relatives in the country. The Wolf range in the kitchen was a delight for preparing family meals. We loved the sauna as we got a few snow flurries and loved warming up there. The...
Modern farmhouse in classic VT orchard setting - stunning sunsets & location

1 Mi to Sugarbush Resort: Dog-Friendly Home!

8.0 out of 10, Very Good, (1)
"This is a SUPERB property, and the owner was really helpful in somewhat challenging circumstances. Unfortunately the driveway was not plowed out when we got to the VRBO (I went to the lower driveway and got stuck inadvertently, not realizing the extent of the snow). It took AAA to pull me out after the plow service came. That being said, despite the tough arrival, we enjoyed the home a lot-- roomy, with many delightful features. Sadly, the impending snowstorm dissuaded the rest of my...
1 Mi to Sugarbush Resort: Dog-Friendly Home!

Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms

10.0 out of 10, Exceptional, (13)
"It was a wonderful stay in a beautiful home close to all of the places we wanted to spend time!"
Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms

Ski-in and Ski-out at Sugarbush Resort at Lincoln Peak

8.0 out of 10, Very Good, (1)
Ski-in and Ski-out at Sugarbush Resort at Lincoln Peak

Stunning Modern Retreat Overlooking The Mad River

10.0 out of 10, Exceptional, (7)
"We only had one night and got there after dark but waking up to the falls and Vermont scenery was such a wonderful start to the day. The local food was amazing and the home is well appointed and has room for all to come together or have individual spaces to relax and unwind. "
The price is AED 814
AED 2,734 total
includes taxes & fees
10 Apr - 11 Apr
Stunning Modern Retreat Overlooking The Mad River

Historic home on 1 acre with snowmobile trails in backyard & mountain views

10.0 out of 10, Exceptional, (22)
"Up skiing for a couple days and found this amazing spot. We will be back! Everything you need for a couple day adventure"
Historic home on 1 acre with snowmobile trails in backyard & mountain views

NEW LISTING! Cozy Trotter (4-Bedroom Home) - Pets Allowed

2.0 star property
10.0 out of 10, Exceptional, (1)
"Clean and nice, perfect mattresses on our beds, we enjoyed out stay."
NEW LISTING! Cozy Trotter (4-Bedroom Home) - Pets Allowed

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

9.2 out of 10, Wonderful, (75)
"We were a mixed group, one family of 4 and two additional adults. So we had private bedrooms for all. The house was a mix of rustic charm and some newer house elements. We were just there one night, so did not spend a whole lot of time at the house, but it was a perfect fit for our needs. Thanks Bethany!"
The price is AED 367
AED 1,148 total
includes taxes & fees
31 Mar - 1 Apr
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

WELCOME TO ON THE ROCK - A RECENTLY RENOVATED BEAUTIFUL LAKE FRONT HOME

10.0 out of 10, Exceptional, (9)
"We just spent a week at this wonderful home overlooking beautiful northern Lake George. The bedrooms were nice, the kitchen nicely updated, and the main room and deck were the ideal setting for a reunion of old friends and our young families. Highly recommend!"
WELCOME TO ON THE ROCK - A RECENTLY RENOVATED BEAUTIFUL LAKE FRONT HOME

Dog-friendly mountain home w/wood stove, deck, firepit, grill, washer/dryer

9.6 out of 10, Exceptional, (29)
"This is a great place for a winter get-a-way. Dealing with VACASA as a property liaison manager left a lot to be desired. When we called about a few issues, they informed us someone would come out and no one ever did. That led to 7 of us using 1 bathroom. The instructions in the house differed greatly with what was written online as well. The house booklet listed certain things as present that were no where to be found. If these issues could be rectified, I would stay there again."
Dog-friendly mountain home w/wood stove, deck, firepit, grill, washer/dryer

4 Mi to Sugarbush Resort: Waitsfield Retreat

9.2 out of 10, Wonderful, (47)
"The location of the house was good for Bolton Valley, and Stowe and great for Sugarbush. The house has all you need for entertainment, comfort and amenities. We especially liked the fast drip, commercial coffee maker! The hot tub was also a hit after skiing each day. Good communication, well maintained and plenty of room. "
4 Mi to Sugarbush Resort: Waitsfield Retreat

Dog-friendly home near Lake George with deck, grill, media room, fireplace, W/D

8.8 out of 10, Excellent, (6)
"We checked in Friday night around 6pm and the driveway and property was very dark with no lights on. Once we entered the house we attempted to turn the outside light on but it didn’t work. The bedrooms downstairs were freezing. We couldn’t locate a thermostat anywhere downstairs.We assumed that meant the heat downstairs was controlled by the upstairs thermostat but it didn’t specify separate zones so we were confused. I went through the welcome book to make sure there wasn’t something we were...
Dog-friendly home near Lake George with deck, grill, media room, fireplace, W/D
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

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (485)
"My wife and I go away for her birthday every year. This year we wanted something cozy and remote. This was perfect. "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (7)
"Owners were very friendly and had everything you could think of, including local trails, equipment to go out on the lake which was included with the cabin games, local eats, etc."
The price is AED 531
AED 681 total
includes taxes & fees
29 Mar - 30 Mar
Trout House Village Resort

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (234)
"We thoroughly enjoyed our 3 nights at Little Loft. We needed some R&R and that’s exactly what these few days were. We grilled, enjoyed the view with a snowy day/night, melted in the hot tub, and chilled by the fireplace at night. The cabin had everything we needed and then some. Communication was perfect. We couldn’t have asked for a better experience."
Cozy Loft for two with Hot Tub & Mtn Views
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.