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

Luxury Condo Tucked in the Heart of Killington
We really enjoyed our stay at this super cute Airbnb! The location was perfect — just a quick drive to everywhere we wanted to go, which made exploring the area super convenient. The space itself was clean, cozy, and had such a charming vibe. One thing to note is that there’s no AC, which I didn’t realize ahead of time. It wasn’t a dealbreaker by any means, but as a cold sleeper, it was a bit warm for me in June — just something to keep in mind depending on the season. Overall, it was a lovely place and a great spot for a getaway!

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
My daughter and her husband with adult sitters stayed here to attend a wedding. Some of us stayed at the Downtown Marriott. They have three small children and enjoyed the pool. House was nice and in a great location to downtown .

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
Diana and family were amazing super friendly, accommodating and checked in on use through out. We arrived later than expected but Diana waited for us and showed us around the property. We even got to see her dogs, meet her family, met the horse on the property behind and great conversations with Diana. She made us feel right at home. She prepped the pool for us, left us some good snacks and offered lots of recommendations. When you visit check out the theater set up, it’s pretty cool with insane sound system and clear video. Comfortable beds and all around beautiful property. If you visit in the summer it is a little warm on the second floor but we cooled off in the pool and just made sure to turn the fans on. It was the perfect birthday trip, relaxing, private and homey. My family and I are already looking forward to the next trip. Thank you to Diana for everything and hope we can meet again! 100% recommend.
Weekly house rentals

Historic Rideout 16m to Okemo Walk to Town
The place was great for our friend-reunion. We have a bunch of little kids and he space worked well for 5 families. Lots of bedrooms and far enough from common spaces that they were very quiet. The open kitchen/living room was our hub. The fireplace provided a great ambiance. The house is older, charming, and well taken care of. Weston is a classic southern VT town. Fun to walk into town for VT country store, ice cream, etc. There is also a playground that is open to the public at The Little School in town. Town Green is also a good place to hang out. It worked well for our little ones.

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.

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.

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.

Mountain View Getaway
My partner and I were craving a weekend getaway to unwind and escape our hectic schedules. Nicole’s place was the perfect fit! It was exactly as depicted in the listing - quiet, private, and with a breathtaking view of Mt Tabor. Manchester, VT, was just a short drive away, offering a delightful mix of shopping and dining options. This place exceeded our expectations and was exactly what we needed!

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

Green Mountain Dreams
The places exactly what how it was described. Spacious and clean! Would come back if we go back to Okemo!

Artist Forest Retreat
Really lovely cabin with beautiful open design and decor. Reasonable drive to Magic Mountain and the surrounding area for skiing and other winter sport activities, and a great bathtub for your sore muscles afterward. Heat was super effective, hot water didn't run out even with four of us showering back-to-back, kitchen was well-supplied and there's a nice big driveway with plenty of room to park and turn around. There was even a closet full of boardgames; we played a lot of Scrabble. Of note — like much of Vermont, this is on a gravel/dirt road and it would be a bit sketchy to get there without good tires and four wheel drive. It also snowed a couple times while we were there and the stairs up to the house get very icy. So generally, if you're going in winter, be prepared.
Private house rentals

Ludlow Lake & Ski Cottage - Adventure Awaits!
Exceptional experience! This is one of the relaxing place I have ever been! Large windows give you sense of experience living in nature. The stunning view gives you awesome feeling in any weather conditions.The house is nice, clean and equipped with pretty much everything. They have all the utensils for cooking and lots of toys for kids both indoor and outdoor. They also have paddles boat and kayak to use at anytime ! In addition, Brian is very respectful, responsible and quick to respond for any questions. All together Feel like you live in your own house. Great vacation spot without any doubt.

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

Modern Chalet: Magic Mountain
Tyler’s place exceeded expectations! The home was exactly as advertised—beautiful, spotless, and in a fantastic location. Check-in and check-out were seamless, making our stay even more enjoyable. Tyler was an outstanding host, incredibly responsive, and went above and beyond by providing detailed information and fantastic restaurant recommendations. I’d highly recommend staying here to anyone looking for a top-notch experience!

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.

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.

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!

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
$128 SGD 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
- Lake George Expedition Park
- Fort Ticonderoga
- 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
- Brattleboro Ski Hill
- Bretwood Golf Course