
House vacation rentals in Middlebury
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Top-rated house rentals in Middlebury
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Popular amenities for Middlebury house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington
Comfortable and convenient location. Everything we needed was in the kitchen. We had most of our meals in and took advantage of the kitchen. The sleeping accommodations were very comfortable. It is only a short drive to Killington, where my family skied. We would definitely stay there again.

Epic Views of the Green Mountains
Great place to take your family if you like to escape from humanity! Very remote setting and plenty of places to hike. The house is as described and the kitchen if fully stocked to make full dinners. My daughters, our German Shepard and I had a wonderful time. Suggestions - bring groceries as Granville is in the middle of nowhere. Closest store is in Rochester, 12 miles South. William was very commun icative and the value for the money was phenominal. Hope I can return next year!

Spacious Retreat mins to Lake George pool&hot tub
We had a wonderful stay! Victoria was extremely generous and accommodating, making sure all our requests were taken care of and that check-in was smooth and hassle-free. The house itself was beautiful—neat, tidy, and very well maintained. The rooms were clean, the washrooms were spotless, and the overall atmosphere was warm and welcoming. Victoria was always quick to respond to any questions we had, which made the entire experience even better. Highly recommend!

Ranch at Mendon Mt Orchards
Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay again!

SugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace
Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.

Charming Sugarbush Standalone Condo
Great location and lots of space. We were able to ski in/out (look for "Cliff's Road" sign when skiing back) fairly easily, which was nice. Would definitely stay here again. Thanks!

2 Bedroom House part of duplex in the Village
The staff at The Heritage were outstanding. Ray was god sent, he went above and beyond everyday. Not many left like him.

Cool Pool, a Private Oasis
Lovely house and beautiful lot! Spent lots of time playing in the yard, swimming in the pool and exploring all the things that Stowe has to offer. We'll be back!
Weekly house rentals

Modern Home in Lincoln Sauna / Pond / Ev Chg / Pvt
Bjorn’s home is pristine and could not be nestled in a more beautiful place. He was very responsive and the house is well supplied with everything you could need. Highly recommend and look forward to staying here again!!

FULL HOUSE w/HOT TUB - Waitsfield Common
This home is beautiful, spacious and is surrounded by nature. The backyard had a huge deck with a tree lined backyard and you can hardly see the next neighbour. There are rolling hills and cows in the next pasture. So serene. The house has lots of room in the main area for our family, it never felt crowded. The kitchen looks better then the pictures, with a huge island and the entire house is fully stocked. You can tell this is not just a rental as it had more then we expected to live comfortably. She was also kind enough to bring us some baby items. The location is great as wherever you turn it's beautiful but also within driving distance to Stowe. The local towns are really cute too. Our family really enjoyed our time here.

Killington/Okemo, 7p Hot tub, Mtn.views, Spacious!
This place was beautiful, and so much bigger than the pictures!! We loved how private it felt, and it was just a short walk to downtown! Would recommend to anyone coming to this area, and would gladly stay again ourselves!!

Beautiful guesthouse -perfect for long stays
Very nice host !! Airbnb was very cozy and accessible, would highly recommend :)

Spacious Winooski Oasis, close to downtown!
We had a great stay here. The house was quaint and exactly as pictured. We asked for recommendations but didn’t receive a response. However, Sam was super responsive for all other things house related like check in time and when the shower pump was broken and only giving us cold water. The hot water issue was taken care of right away which was appreciated! The backyard is big and fenced in. This is great for dogs! There is a grill and fire pit. We didn’t use either but having that amenity was nice. Location is great and so was the price. Walking distance and car ride from most eateries and cute shops. We felt safe, thank you!

New Remodel w/VIEWS! on 20 Acres!
Kim was super kind and went above and beyond to help me sort out a situation even before our arrival. The home is located in a quiet beautiful area, it is super comfortable, beautifully decorated. The beds were very comfortable. We had plenty of towels and linens. My kids enjoyed playing games in the basement, and my husband and I enjoyed watching TV and reading by the fireplace. I highly recommend Kim's place.

Chillbilly Bolton Haven-hot tub
My family of 3 met up with another family of 3 for a little winter weekend getaway. The location was perfect, less than 15 mins to LG for the winter carnival and 1 min car ride to The Barrel where we had reservations to eat in the igloos. The house was absolutely beautiful and very clean. It had everything we could ask for available for us. We loved going in the hot tub at night and then sitting inside next to the fireplace. It snowed while we were there which made the hot tub and views even more enjoyable. Someone was there to shovel and plow so we didn’t have to do any work. We definitely would like to return during the warmer months to use the kayaks and go to the beaches. Michelle sent recommendations which we greatly appreciated and responded very quickly to any messages. 10/10 would recommend!!

Beautiful Vermont Farmhouse with stunning view
We had a wonderful weekend getaway at this unique and charming farm-style property. The house has a cozy and inviting atmosphere, equipped with everything you need for a relaxing stay with family or friends. Located in a peaceful and quiet area, it’s just a short 10-minute drive to town, making it the perfect combination of seclusion and convenience. We stayed here while snowboarding at Killington, and it was a fantastic base for our trip. Susan, the host, made our stay even more memorable with her personal touch. She gave us a warm welcome through a call, providing a quick orientation and offering excellent recommendations for activities and places to visit in the area. Her attention to detail and thoughtfulness truly stood out. Highly recommended for anyone looking for a serene and unique escape!
Private house rentals

Spruce Hollow Hideaway “Hot Tub”
This place was perfect for our large group. To start plenty of parking in the drive way. Plenty of room in the house for everyone to not feel on top of eachother. The hot tub was great after a few long days of skiing. Lastly if you’re looking for a place close to the mountain it doesnt get much more convenient than this location. Also plenty of places to grab drinks or food near by. Would definitely stay here again

Cozy Private House on Killington Mtn - Hottub
This airbnb was even better than we expected! It is just minutes away from all the Killington lodges and the restaurants/bars in town. The house was extremely clean, easy to find, and perfect for a group of skiers. I highly recommend it for anyone looking for a beautiful, easy place to stay at Killington. Would love to stay here again next time we visit! Highly recommend.

4 story 3BR 2BA sunlit house w/ gorgeous mtn views
Very unique house with incredible views. Great location for getting outside, and had everything we needed. Was perfect for skiing and we would love to see this place in the summer!

Killington Chalet -Very Close To Slopes!
Went here with a large group of friends for a skiing trip in Killington and the location and house was perfect for what we needed. Herb was extremely responsive to all questions and concerns we had, would absolutely recommend staying here if your a skier/border or are just trying to experience the area with a large group of people!

Huge deck, hot tub, foosball, surrounded by nature
Great stay at Jen’s beautiful chalet. Easy to communicate with and well equipped with many kitchen supplies and all the needed towels, linens, hairdryers, and a thoughtful welcome package. Only about 15 mins from the mountain and 10 mins to town. Thanks!

LaFlame Chalet - 10 mins to Sugarbush
We had a great stay at this cozy Airbnb. Looks exactly like the pictures and is a perfect size for group of friends or family. We brought a dog and had no issues at all. The hosts were very kind and even helped us with some car troubles after an unexpected snow storm. Would recommend and overall great stay!

Lovely private house in the mountains
We had a very nice stay, especially appreciating the proximity to Sugarbush and the responsiveness of the host.

Comfortable, relaxing large country home
Great spot for a week of skiing! Danielle was very helpful and communicative throughout
Quick stats about house rentals in Middlebury
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ257 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Okemo Mountain Resort
- Sugarbush Resort
- Smugglers' Notch Resort
- Spruce Peak
- Gore Mountain
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Whiteface Mountain Ski Resort
- Northeast Slopes Ski Tow
- Fort Ticonderoga
- Cochran's Ski Area
- Ethan Allen Homestead Museum
- Country Club of Vermont
- Vermont National Country Club
- Lincoln Peak Vineyard
- Cozy Cottages & Otter Valley Winery
- Adirondack Extreme Adventure Course
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Burlington Country Club
- Leahy Center for Lake Champlain
- Fox Run Golf Club
- Killington Adventure Center
- Montshire Museum of Science