
House holiday rentals in Weston
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Top-rated house rentals in Weston
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Popular amenities for Weston house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington
Very nice place easy access to routes 4 and 100 with plenty of things to do

Magical Farm Getaway - a must visit!
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!

Ranch at Mendon Mt Orchards
We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

Adams Farm-"The Little Farmhouse"
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.

SugarBear- Pool, AC, Sauna, Gym, Tennis!
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.

The Brick House on Washington Street
Great stay and was exactly what we needed for our entire family for a weekend wedding!

Historic Home on 17 acres of land. Go escape!
Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩

Hollywood Bungalow in the Berkshires #C0191633410
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.
Weekly house rentals

LittleHouseinthe Woods
Lisa's little cabin was just perfect for my husband and I and our 2 pugs. However i could easily have had firends come with us and the cabin would have been roomy enough for all of us. its 10 mins from Okemo which is great. and the town of Weston for the Vermont country store and Leylas is great. Manchester only 30mins away. the cabin is perfectly situated in-between everything.

Breathtaking VT Getaway
House and location - the house is beautiful and the view from the backyard is amazing. The location was as described. It was also great that the host shared that the cell service around the house is poor. Amenities - the amenities were great. We cooked while we stayed and the kitchen was fully stocked with anything we could possibly need. Including things like serving platters and bowls. It was also great that the fireplace was useable and stocked with wood. Extra - it snowed like crazy when we stayed. Having the plow service helped us in the driveway greatly! One edit to the listing - Belmont General Store was closed when we stayed.

Magical Retreat in Londonderry, 3 bd, EV charger
Beautiful, spacious house, just as described. Clear instructions and responsive hosts.

Lux Family Retreat @ Okemo/Bromley. Arcade Machine
Idyllic location and accommodations for our family of 9 . Thoroughly enjoyed the cozy fireplace (wood provided by owners) every night and place so accessible to town and skiing. Will very much look forward to staying here again Brian was so responsive and owners , while on site, were not in our way!

The Bluebird Day Chalet 2 bed dtwn Ludlow Village
Great place! Right downtown near everything and super walkable. Nice rooms, clean and tidy! Would recommend, perfect for a weekend get away.

Mountain View Getaway
We loved our stay at Nicole’s place. It was very peaceful and private- just what we needed! Our dog also felt right at home thanks to her welcoming touches. We would definitely stay there again!

Vermont Mountain Escape
The house is fantastic and I highly recommend it to anyone who’s planning a trip to the area. Austin’s place is very stylish, comfortable and has everything that’ll make your stay an enjoying experience. You’ll find nice touches and well-thought details throughout the house the moment you step in. Location is also amazing to have a safe and peaceful stay with beautiful surroundings while being close to all nearby actions. We had a great ski trip overall and already planning to be back.

VT Cabin sitting above the West River and Village
great small cabin nested in a small VT town! Rachel was great and we were within 20 minutes of Stratton which was perfect for our quick weekend
Private house rentals

Mid-century Modern Mountain House! Renovated!
Lovely home, in a beautiful setting. The house was spaceous, yet cosy, with 2 wood burning fireplaces, and everything we needed for a perfect winter vacation. The house is well situated, allowing us to enjoy skiing, in Stratton, Okemo and the more local mountain - Bromley. Our kids and dogs also had a blast sledding in the yard. Kelsey was a great host, providing lots of local recommendations and was extremely responsive. Thank you for sharing your place with us.

Magical Retreat Cottage - Waterfalls Everywhere
Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.

Country House in the Woods
This was a perfect place for our group of 3 couples and 2 kids. Plenty of space, 15 min from Okemo for skiing and well-stocked for cooking in. We enjoyed the amazing stars from the hot tub at night! Brien and Victoria were super responsive and helpful.

Vermont Mirror House
I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.

The Aster Chalet: a modern family retreat
This place was beautiful! We enjoyed all of the little touches including the thoughtful snack platter, the night lights around the house, sound machine, games, fireplace, and the comfy blankets. The mud room cubbies were so great for all of our ski gear. It really does look just like the photos. So modern and clean. Very pleased with our stay.

Okemo Mountain House & Private Hot Tub
Julie’s place is fantastic. Great location close to the grocery store, downtown, and Okemo Mountain Resort. Awesome fireplace. Great kitchen. Gadgets for drying ski gloves/mittens and ski boots were very cool. Highly recommend!

Black Star Barn, Mountain Retreat w/ Hot Tub
We were 2 couples and had the perfect stay! Really cozy house with a great porch and hot tub! We loved playing ping pong as well! Would 100% stay there again!!

Vermont Charm in the 1840 Gideon Lee House
We have had a marvelous time at Gideon Lee in Chester, Vermont. An extremely spacious house, equipped with all the necessities. A well-functioning kitchen, a washer and dryer and especially a cozy "wood stove". Polly and Ian are friendly and interested people with whom you are happy to strike up a conversation. And who are happy to give all kind of suggestions for trails, restaurants, or just for visiting nice villages. In the five days we were there, this house became a home!
Quick stats about house rentals in Weston
Total rentals
40 properties
Nightly prices starting at
$166 NZD before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Berkshire East Mountain Resort
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Ragged Mountain Resort
- Fort Ticonderoga
- Lake George Expedition Park
- Dorset Field Club
- Autumn Mountain Winery
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Clarksburg State Park
- Ekwanok Country Club
- Hooper Golf Course
- Brattleboro Ski Hill