House holiday rentals in Weston

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Popular amenities for house rentals in Weston

House rentals with a pool

Guest favourite
Home in Killington
4.91 out of 5 average rating, 213 reviews

Luxury Condo Tucked in the Heart of Killington

JessicaRating, 5 stars1 day ago
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!
Guest favourite
Home in Salem
4.98 out of 5 average rating, 192 reviews

Magical Farm Getaway - a must visit!

BriannaRating, 5 stars3 weeks ago
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!
Top guest favourite
Home in Mendon
4.89 out of 5 average rating, 247 reviews

Ranch at Mendon Mt Orchards

RobinRating, 5 stars1 month ago
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!
Superhost
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars4 months ago
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.
Top guest favourite
Home in Killington
4.99 out of 5 average rating, 135 reviews

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

JennRating, 5 stars1 month ago
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.
Guest favourite
Home in Keene
4.93 out of 5 average rating, 212 reviews

The Brick House on Washington Street

CarolRating, 5 stars1 day ago
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 .
Guest favourite
Home in Plainfield
4.89 out of 5 average rating, 139 reviews

Historic Home on 17 acres of land. Go escape!

BrandieRating, 5 stars3 months ago
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!! 🤩
Guest favourite
Home in Williamstown
4.89 out of 5 average rating, 220 reviews

Hollywood Bungalow in the Berkshires #C0191633410

EveRating, 5 stars1 day ago
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

Guest favourite
Home in Weston
4.85 out of 5 average rating, 33 reviews

Historic Rideout 16m to Okemo Walk to Town

WarrenRating, 5 stars8 months ago
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.
Guest favourite
Home in Weston
4.95 out of 5 average rating, 19 reviews

Mid-century Modern Mountain House! Renovated!

CatherineRating, 5 stars4 months ago
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.
Guest favourite
Home in Ludlow
4.9 out of 5 average rating, 93 reviews

The Bluebird Day Chalet 2 bed dtwn Ludlow Village

NikkiRating, 5 stars1 week ago
Great place! Right downtown near everything and super walkable. Nice rooms, clean and tidy! Would recommend, perfect for a weekend get away.
Top guest favourite
Home in East Dover
5 out of 5 average rating, 50 reviews

Magical Retreat Cottage - Waterfalls Everywhere

DavidRating, 5 stars1 week ago
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.
Guest favourite
Home in Dorset
4.91 out of 5 average rating, 53 reviews

Mountain View Getaway

AnthonyRating, 5 stars2 days ago
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!
Guest favourite
Home in Londonderry
4.92 out of 5 average rating, 73 reviews

VT Cabin sitting above the West River and Village

JoshuaRating, 5 stars3 months ago
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
Top guest favourite
Home in Weston
5 out of 5 average rating, 37 reviews

Green Mountain Dreams

BlairRating, 5 stars4 months ago
The places exactly what how it was described. Spacious and clean! Would come back if we go back to Okemo!
Guest favourite
Home in Grafton
4.93 out of 5 average rating, 75 reviews

Artist Forest Retreat

MiraRating, 5 stars3 months ago
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

Top guest favourite
Home in Ludlow
5 out of 5 average rating, 33 reviews

Ludlow Lake & Ski Cottage - Adventure Awaits!

MdRating, 5 stars1 week ago
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.
Top guest favourite
Home in Londonderry
5 out of 5 average rating, 21 reviews

Magical Retreat in Londonderry, 3 bd, EV charger

TsvetelinaRating, 5 stars4 months ago
Beautiful, spacious house, just as described. Clear instructions and responsive hosts.
Top guest favourite
Home in Londonderry
5 out of 5 average rating, 12 reviews

Modern Chalet: Magic Mountain

RileyRating, 5 stars3 months ago
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!
Top guest favourite
Home in Andover
4.94 out of 5 average rating, 16 reviews

Country House in the Woods

StaceyRating, 5 stars4 months ago
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.
Guest favourite
Home in Guilford
4.92 out of 5 average rating, 50 reviews

Vermont Mirror House

GeorgeRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Mount Holly
5 out of 5 average rating, 10 reviews

Vermont Mountain Escape

CanerRating, 5 stars4 months ago
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.
Top guest favourite
Home in Ludlow
5 out of 5 average rating, 42 reviews

Okemo Mountain House & Private Hot Tub

DustinRating, 5 stars3 months ago
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!
Top guest favourite
Home in Chester
5 out of 5 average rating, 25 reviews

Vermont Charm in the 1840 Gideon Lee House

CarloRating, 5 stars1 month ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Weston
  6. House rentals