House vacation rentals in Weston

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Popular amenities for Weston house rentals

House rentals with a pool

Guest favorite
Home in Killington
4.91 out of 5 average rating, 212 reviews

Luxury Condo Tucked in the Heart of Killington

KennethRating, 5 stars6 days ago
Very nice place easy access to routes 4 and 100 with plenty of things to do
Guest favorite
Home in Salem
4.98 out of 5 average rating, 191 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars3 months ago
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!
Guest favorite
Home in Colrain
4.9 out of 5 average rating, 129 reviews

The 1770 House

CatherineRating, 5 stars3 weeks ago
Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!
Top guest favorite
Home in Mendon
4.89 out of 5 average rating, 247 reviews

Ranch at Mendon Mt Orchards

RobinRating, 5 stars3 weeks 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 favorite
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 favorite
Home in Keene
4.93 out of 5 average rating, 211 reviews

The Brick House on Washington Street

PaulRating, 5 stars6 days ago
Great stay and was exactly what we needed for our entire family for a weekend wedding!
Guest favorite
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!! 🤩

Weekly house rentals

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

Historic Rideout 16m to Okemo Walk to Town

WarrenRating, 5 stars7 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 favorite
Home in Weston
4.95 out of 5 average rating, 19 reviews

Mid-century Modern Mountain House! Renovated!

CatherineRating, 5 stars3 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 favorite
Home in Ludlow
4.9 out of 5 average rating, 92 reviews

The Bluebird Day Chalet 2 bed dtwn Ludlow Village

BrianRating, 5 stars2 months ago
It is a great place. Convenient to downtown and a short ride to Okemo.
Guest favorite
Home in Dorset
4.92 out of 5 average rating, 50 reviews

Mountain View Getaway

OliviaRating, 5 stars1 week ago
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!
Top guest favorite
Home in Chester
4.98 out of 5 average rating, 50 reviews

Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain

LuisRating, 5 stars2 weeks ago
Great stay! The Chalet is nice and secluded. A Great way to getaway with friends and/or family. The size of the stay is great for those looking to spend time intimately. Everything you see is what you get. There were no complaints with our stay and that is why it deserves a 5 ⭐️. The hosts are kind enough to have had firewood available for use of the fire pit. The hosts were both hospitable and responsive. I hope to stay there again maybe in the winter to go skiing or snowboarding. The towns of Ludlow and Springfield are roughly 15 minutes away in their respective directions with tons of dining options and activities. New England Cider donuts is right on Main St. in Ludlow which is a great spot for breakfast sandwiches and pastries. Okemo Mountain is a great hiking experience also found in Ludlow. If you find yourself looking for a quiet and peaceful getaway, don’t give it a second thought and just book this place you won’t regret it!
Guest favorite
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 favorite
Home in Chester
5 out of 5 average rating, 24 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!
Top guest favorite
Home in Weston
5 out of 5 average rating, 37 reviews

Green Mountain Dreams

BlairRating, 5 stars3 months ago
The places exactly what how it was described. Spacious and clean! Would come back if we go back to Okemo!

Private house rentals

Guest favorite
Home in Andover
5 out of 5 average rating, 6 reviews

River House w/ Hot Tub! Close to Mountain & More

JessicaRating, 5 stars4 months ago
This house was the best ski weekend away! Conveniently located yet secluded for a peaceful stay. The home itself is spacious, charmingly rustic, and thoughtfully stocked with everything we needed—especially the fully equipped kitchen, which made cooking a breeze. The atmosphere was cozy and inviting, making it the ideal spot to relax and unwind. Highly recommend.
Top guest favorite
Home in Argyle
5 out of 5 average rating, 18 reviews

Lakefront gem

RebeccaRating, 5 stars1 month ago
Our stay at the lake was truly amazing! The house was impeccably clean and well-maintained, and the location was perfect for enjoying the lake. Lisa was incredibly responsive and helpful throughout our stay. Highly recommended!
Superhost
Home in Andover
4.83 out of 5 average rating, 40 reviews

Cozy private cabin near Okemo! Large Hot tub!

SamanthaRating, 5 stars1 month ago
This cabin was a cute stay! Please was clean and cozy. No issues with check in, it’s code access and all the details was sent the day before. Was a perfect place for our weekend getaway with the dog
Top guest favorite
Home in East Dover
5 out of 5 average rating, 49 reviews

Magical Retreat Cottage - Waterfalls Everywhere

ManpreetRating, 5 stars3 months ago
Gene was the absolute best from before our trip started until the very end! His retreat was beautiful and very well kept with great amenities, looking forward to check it out in the summer!
Top guest favorite
Home in Andover
4.94 out of 5 average rating, 16 reviews

Country House in the Woods

StaceyRating, 5 stars3 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 favorite
Home in Guilford
4.92 out of 5 average rating, 49 reviews

Vermont Mirror House

GeorgeRating, 5 stars5 days 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 favorite
Home in Windham
5 out of 5 average rating, 11 reviews

The Aster Chalet: a modern family retreat

LisaRating, 5 stars2 months ago
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.
Top guest favorite
Home in Londonderry
5 out of 5 average rating, 33 reviews

Black Star Barn, Mountain Retreat w/ Hot Tub

FarynRating, 5 stars3 months ago
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!!

Quick stats about house rentals in Weston

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$20,915 GYD 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

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