
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.

Private Escape! Pool, 10pp.22 acres, Near LG
We had an amazing long weekend at Jim and Jen’s place! There was so much space to spread out, but also be together. The yard was amazing, kitchen had everything you could need, and as parents of 20 month olds, having all the outlets covered and no clutter they could get into was so nice. Would def recommend this place for families!

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!

Private 5BR Mt. view, pool, new hot tub
This house was incredible. Open concept first floor to gather for making dinner and eating around the table. Incredible views of the Mad River Valley, a hot tub, and room downstairs to hang out. Highly recommend for a weekend of skiing.

Remodeled Home - Private Pool - Lower Village- 4bd
We have stayed at this location a number of times of times. Winter, Spring, Summer and fall and it never disappoints. Great location, close enough to the action but very peaceful. I stayed there with my family and kids (6 and 2) and it is perfect. I have also stayed there with buddies for all ski weekend and also perfect! House is extremely comfortable and impeccably maintained. Amenities are as advertised. Bob is a great and responsive host, though with the way the place is kept and the great instructions provided you likely won’t need to contact him. Really, get this place. You won’t be disappointed!

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!

Winter Wonderful Waitsfield Spacious VT Home w/Spa
Our stay in Sara and Mikes home in Waitsfield was incredible! Upon arrival into the mad river valley, the surrounding views were instantly beautiful and calming. The moment we stepped in the house we honestly felt right at home. The layout of the house is so calming and tasteful. Everything is perfectly organized, down to the labeling for all of the dishes and cookware so you’ll never have trouble finding what you need! Waking up and heading by downstairs for a workout in the home gym, followed by a dip in the hot tub on the secluded back deck was an insanely relaxing way to start the day. The custom built bed frames/furniture and the overall craftsmanship of the space added a comforting artistic value to the stay. Don’t get me started on the screen porch! This house is full of amenities and I’ve honestly never felt more at home at an air b&b stay. Nice quiet respectful neighborhood in an amazing community, would recommend this spot to anyone and we hope to return in the future!

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!
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!!

Large New England Home w/ Gorgeous Mountain Views
This is a great house to stay in. There's a lot of space, places to sleep, sit and relax, eat, watch tv, play games, work, read, cook. Plenty of hot water.. Very private, although in a neighborhood. Nice back yard area when not covered in snow, looking up at the mountains behind. Sheri is top notch. Easy to reach, super friendly and helpful, easy going. We came at the tail end of a snow storm, but the driveway was cleared enough to get our car in and then Sheri worked with us to make sure everything was cleared before we had to go out the next day. Easy walk into the cute town of Bristol. Handful of nice shops (books, games, art, crafts, gifts, toys) and restaurants: Wokky's--ok Chinese/great staff; Minifactory--out of sight coffee/biscuits/sandwiches/fresh ingredients/lot of gluten free; Cubber's--locals' joint/excellent pizza/sandwiches; Farmhouse Chocolates--superb fresh organic truffles, bars, caramels/chocolatier is wonderful. Easy drive to Mad River Glen, Sugarbush for skiing.

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.

South Hill Lodge- 5 BR Post & Beam Home
Beautiful home, as described. Nice personal touches with towels and mini shampoo/conditioner. Kitchen is large and has most every appliance you would want. Caretaker does come in twice per day but is friendly and unobtrusive. You do need AWD/4WD to access the house.

Bolton Home Away from Home-hike, beach, boat, ski
My family and I had a wonderful stay at the home over a long Labor Day Weekend. The house and property are top-notch, as advertised. The house is extremely well outfitted (kitchen, towels, linens, everything) for a group of our size and larger (we had six). Very nice outdoor patio. Michelle was an excellent host. Communication from reservation through check-in and out was great. Location is a major plus for me. Short walk to downtown Bolton Landing. Short walk to the marina where we had a rental boat. I think that I'm a tough grader- though I haven't lived in the area for a very long time, I grew up on the lake and my family (kids all grown adults) and I all agree that we would happily look for an opportunity to visit this property again. - Tom

Killington Retreat | Deck-Fire Pit-Mountain Views!
Jeff was an awesome host. He shared the instructions to get to the house and all things to do around the house. Followed up with us once we got there about our experience to check in and made it very easy for us. The house is great and we enjoyed every bit of it. The best place is the deck overlooking the mountains. We did lot of grill and enjoyed eating on the deck. Kitchen was pretty well organized with all the utensils and literally everything was available, even if we missed carrying few things from home, it would have been available at the house. Kids enjoyed board games and watching TV. Best experience we had in recent times.

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.

The Summerwind Lodge
Jeanette was an amazing host, so responsive, and the lodge was beyond our expectations! The location is absolutely incredible. I can't recommend it enough!
Private house rentals

Mountain Cottage for ski weekend. Pet Friendly!
The house was perfect and Nicole was a fantastic and responsive host

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.

Beautiful Historic Estate In Heart of Adirondacks
Anna’s place is nothing short of magical! It was an extraordinarily special place for a family holiday. It is a one-of-a-kind space. Looks just like the photos. It is beautiful and cozy and feels historic and warm. The kitchen is wonderfully up to date - a dream to cook and gather in. Anna was completely responsive and helpful. I cannot recommend Anna and her place highly enough !

The North House - 100 acres of Adirondack privacy
Amazing secluded place in the middle of the woods with all amenities. Beautiful and well designed to every detail . We really enjoyed the stay with our family

The Tree House on Lake George
The house was beautiful as it was captured in the pictures. Connor was extremely helpful and communicative when we needed help. Despite the snow storm, we had an easy time getting in and out of the house. Extremely beautiful surroundings,great views / vistas from every window, abundant light. House heated well despite the cold weather and kitchen was truly stocked with everything needed, especially for foodies like us who love cooking. Would definitely be back!

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!

Entire House in Bolton Landing, NY
It was truly delightful! Our group had an amazing time creating lasting memories in this stunning space. The home was impeccable clean and well-maintained, which added to our overall enjoyment. We loved the variety of activities available, including a theater room, game rooms, television in every bedroom, a fireplace and a hot tub. I forgot to mention the wrap around deck. Although we didn't get a chance to use the hot tub, it was fantastic addition to the property. Overall, we had a wonderful experience and took plenty of pictures to cherish the memories. I highly recommend this Airbnb for anyone looking to enjoy a luxurious getaway in Lake George.

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!
Quick stats about house rentals in Middlebury
Total rentals
30 properties
Nightly prices starting at
$70 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
- Gore Mountain
- Spruce Peak
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Whiteface Mountain Ski Resort
- Cochran's Ski Area
- Country Club of Vermont
- Fox Run Golf Club
- Lucky Bugger Vineyard & Winery
- Montshire Museum of Science
- Vermont National Country Club
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