
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

Just an Incredible Vermont Mountain Retreat
My family and I enjoyed four days at the cabin, and it was exactly what we needed! Couldn't have been happier with our stay. We enjoyed the property's seclusion but also that it wasn't too far from several towns and ski resorts--truly a win-win. Would definitely come back.

Luxury VT Retreat. Breathtaking Views & Sunsets
First and foremost, Julia is one of the most accommodating and most responsive hosts I’ve ever had. She was very friendly and proactively looked for ways to help me and my group feel welcome. Beautiful space scenically located on a Vermont mountainside - would absolutely recommend!

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.

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!

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.
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.

Cozy private cabin near Okemo! Large Hot tub!
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

Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
Nice and quiet out of the way place. Perfect for a quick getaway for a few days. We will definitely be going back.

Modern VT Farmhouse w/Hot Tub & Fire Pit
This place was truly me & my husband’s ultimate favorite place to have a peaceful vacation thus far. We loved how spacious and together everything felt, from having so many windows and the theming through the whole house was truly unique and thoughtful. Sure there is a camera looking dead at you while in the hot tub, but most likely it’s because there’s an entrance right there. Outdoors is nature central: river close by, all types of birds chirping and surrounded by trees. Kitchen was equipped with seasonings & stocked with pots and utensils. Host was super helpful & responsive for sure. Overall: 10/10! Don’t hesitate to book! Really wonderful stay!!

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!

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

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
$155 AUD 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
- Bretwood Golf Course
- Brattleboro Ski Hill