House holiday rentals in Weston

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Popular amenities for Weston house rentals

House rentals with a pool

Top Guest favourite
Home in Cambridge
4.97 out of 5 average rating, 39 reviews

Country hideaway

GwenRating, 5 stars7 months ago
Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!
Guest favourite
Home in Killington
4.9 out of 5 average rating, 199 reviews

Luxury Condo Tucked in the Heart of Killington

NateRating, 5 stars2 weeks ago
Perfect location close to Killington but with more space and privacy than the hotels and condos in town. The condo was very cozy and we felt right at home. Can’t wait to come back again!
Guest favourite
Home in Salem
4.98 out of 5 average rating, 190 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars1 month 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!
Top Guest favourite
Home in Mendon
4.88 out of 5 average rating, 243 reviews

Ranch at Mendon Mt Orchards

IreneRating, 5 stars2 weeks ago
I had a great time with some friends here on a ski trip. The house had everything we needed to cook breakfasts and dinners, with a surprisingly spacious living room area. Great location and lovely welcome when we arrived. I’m looking forward to coming back again!
Superhost
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars1 month 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
4.98 out of 5 average rating, 133 reviews

SugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace

JeffreyRating, 5 stars4 weeks ago
Dan and Holly are wonderful hosts. Excellent condo unit in a quiet, private location yet very close to great skiing, excellent restaurants, and live music. Condo was spacious, clean, and well kept. Dan and Holly obviously really care about their guests. Highly recommended.
Guest favourite
Home in Hartland
5 out of 5 average rating, 10 reviews

Private Farmhouse with in ground pool!

ChrisRating, 5 stars7 months ago
My family and I truly enjoyed our time spent at the farmhouse. Everything was as expected from the listing. The pictures do not do justice for the property. It's beautiful and well maintained. The pool was nice, warm, and clean. There are yard games readily available and a nice fire pit area. Brin and Maria are super responsive and left very detailed instructions on the property for you. Everything you need is there minus food, which is a 12-minute drive towards a few different grocery stores. The hill is so fun to roll down, too! Thank you so much!
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 stars1 month 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

Superhost
Home in Killington
4.89 out of 5 average rating, 286 reviews

25 Rocky Ridge Road: Ski Home for Groups. Hot Tub.

StenioRating, 5 stars2 months ago
House is located only 5 minutes from Killington Resort, and less than 5 minutes to restaurants, markets, bakery. Lots of rooms, very spacious house. Hot tub is a huge plus, great to relax after a full day on the slopes. We would definitely stay there again.
Superhost
Home in Londonderry
4.94 out of 5 average rating, 174 reviews

Clean, Captivating VT Farmhouse near Stratton!

JamesRating, 5 stars1 month ago
Great house, amazing location near Stratton, and Matthew was just great. He was super communicative, and went above and beyond to make sure we were happy with our stay. We'd love to return again.
Top Guest favourite
Home in Sunapee
4.97 out of 5 average rating, 113 reviews

Sunapee Four Season Getaway with a Mountain View

SamanthaRating, 5 stars2 weeks ago
We had an amazing family ski weekend at this house! With four young children, finding a place that accommodates everyone can be challenging, but this house was perfect. It had two cribs, which was a huge bonus for us. The open floor plan made it easy to keep an eye on the kids while still enjoying time together as a family. The hot tub was a great way to relax after a day on the slopes, and there was plenty of space for our entire group to spread out and feel comfortable. The location was also fantastic—just a short drive to Mount Sunapee, making it so easy to hit the slopes. We couldn't have asked for a better place for our weekend getaway!
Guest favourite
Home in Mt Tabor
4.92 out of 5 average rating, 183 reviews

Spring/Summer Fun Treasures Waiting

JustinRating, 5 stars1 month ago
Great place. Was a bit further from Stratton but close to Manchester and Rutland for food options. It is check in with the hosts - clearly in the instructions - which I overlooked upon booking. The place was just as described and the event brought over blueberry muffins which was a nice touch.
Superhost
Home in Cavendish
4.8 out of 5 average rating, 71 reviews

OKEMO MT HOUSE - OKEMO-LUDLOW-JACKSON GORE

RobertRating, 5 stars1 month ago
House fit our need was a good location for skiing at Okemo
Top Guest favourite
Home in Keene
5 out of 5 average rating, 144 reviews

Downtown Hot Tub Escape

CelenaRating, 5 stars1 day ago
Wanted a night away from home with friends and this was perfect. The hot tub was great, plenty of room to spread out in the living room and kitchen, and the table was perfect for playing board games and eating dinner. The place was very neat and clean and I would definitely recommend it. And a highlight for me and my friends…the see-through refrigerator door. We loved it! :)
Guest favourite
Home in Wilmington
4.9 out of 5 average rating, 219 reviews

Wilmington A-Frame- Cozy and Convenient

TommyRating, 5 stars2 weeks ago
Cute little A-frame cabin! This is our third trip here and it's always a fantastic, memorable experience. Jennifer is super friendly and accommodating. We definitely want to come back soon! :)
Superhost
Home in Fitzwilliam
5 out of 5 average rating, 7 reviews

Large summer home on Laurel Lake NH

BetsyRating, 5 stars68 months ago
This is a place that gives families the time, simplicity, and space to relax together and reconnect. All of the happiness and love of many generations fills the air. This is a wonderful setting for extended families and friends to gather. There is a lot for everyone to do at the house, the lake, and in the Monadnock region. This is a one of a kind property that is very special today more than ever.

Private house rentals

Superhost
Home in Manchester
4.87 out of 5 average rating, 23 reviews

Charming Vacation Home in Manchester Center

JakeRating, 5 stars13 months ago
Steal of a deal for this place. Perfect for any couple or family looking to do a vermont ski vacation. Has all the amenities you need, it’s super spacious, it’s right by town, and it’s a short drive to stratton or bromley. Easy 5 stars.
Guest favourite
Home in Keene
4.92 out of 5 average rating, 48 reviews

Little House with Lots to Offer

ColleenRating, 5 stars1 month ago
I stayed at the Tiny House with my significant other and our dog for a small, private getaway during our anniversary. It was a nice, cozy little home for us which we all enjoyed. It was also great to be right next to a grocery store and near downtown Keene for food and activities.
Superhost
Home in Ludlow
5 out of 5 average rating, 18 reviews

2 Units, 1 Home | Perfect for Multiple Families

QiningRating, 5 stars2 weeks ago
The overall experience is good. Just a reminder: the 1st and 2nd floors use separate doors and are not internally connected. However, the location is very close to Okemo and Killington, and the interior decoration is quite good for the price.
Top Guest favourite
Home in Brattleboro
4.94 out of 5 average rating, 121 reviews

Spacious Brattleboro home on river, walk to town

DeborahRating, 5 stars1 month ago
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.
Guest favourite
Home in Killington
4.94 out of 5 average rating, 117 reviews

Cozy Private House on Killington Mtn - Hottub

MeganRating, 5 stars3 weeks ago
This airbnb was even better than we expected! It is just minutes away from all the Killington lodges and the restaurants/bars in town. The house was extremely clean, easy to find, and perfect for a group of skiers. I highly recommend it for anyone looking for a beautiful, easy place to stay at Killington. Would love to stay here again next time we visit! Highly recommend.
Guest favourite
Home in Newfane
4.92 out of 5 average rating, 49 reviews

6 BR Perfect Private Retreat in Vermont!

AlexRating, 5 stars8 months ago
Large house in a very remote area. Approximately 70 acres. It was very relaxing and was nice to enjoy the pool which was professionally cleaned before arrival. The master bath has an incredible view of the mountains and an enormous shower. Pool table was fun and well taken care of. We stayed on probably one of the hotter weekends and the house cooled down at night pretty well just by opening the windows. Most rooms had ceiling fans if no other fans were provided. I can imagine this house would be amazing in the winter or fall too. With the screened in fireplace room and additional fire place inside the main house. You’re also close to 2 ski mountains each about 18 miles away. I could see myself renting again in the future. Thanks again
Superhost
Home in Jamaica
4.94 out of 5 average rating, 173 reviews

Cozy Riverfront Home in beautiful Jamaica

CaseyRating, 5 stars1 month ago
Great place. Very isolated and a beautiful location but still has all the creature comforts. The deck, view, and space are amazing. Fast WiFi, 2 bathrooms, and a dishwasher with garbage disposal are really cool in a rustic location like this. The wood fires hot tub was obviously the star of the show. Clear instructions and good communication for everything. The gas grill and gas fire pit were nice. Every thing was comfortable and great. Stress free. Hope to stay here again, thanks for everything.
Guest favourite
Home in Chittenden
4.91 out of 5 average rating, 89 reviews

Comfortable, relaxing large country home

EdwardRating, 5 stars1 month ago
Great spot for a week of skiing! Danielle was very helpful and communicative throughout

Quick stats about house rentals in Weston

  • Total rentals

    40 properties

  • Nightly prices starting at

    $182 AUD before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    30 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