
House vacation rentals in Weston
Find and book unique houses on Airbnb
Quick stats about house rentals in Weston

Total vacation rentals
Explore 40 vacation rentals in Weston

Nightly prices starting at
Weston vacation rentals start at G$31,393 GYD per night before taxes and fees

Verified guest reviews
Over 1,630 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Weston vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Weston rentals

4.8 Average rating
Weston stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated house rentals in Weston
Guests agree: these houses are highly rated for location, cleanliness, and more.

Lovers Honey Pond Treehouse with hot tub & sauna
Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…Enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!! High speed WiFi 🐣

Newly renovated. Minutes to Slopes & Trails
Healdville Hideaway has 3 acres of rural charm located on the backside of Okemo Mountain. Charm is a plenty in this 1500 SF single story, newly renovated home with views of the mountain & fields full of wildlife. This modern country decorated home provides the perfect comfortable setting for single or multi family enjoyment. The fully functional kitchen is available for making a quick snack or a full meal. The back acreage is perfect for building a snowman or doing a little cross country skiing.

Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Spacious Loft with View
Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

4 Bedroom Family Ski House w/ WiFi, cable!
This family heirloom sits tucked away in the trees just off of Chester Mountain Road. Short trips to Bromley, Okemo, Stratton and Magic Mountains. Sleeps 8 comfortably with room for up to 10 on pull out couches. You will fall in love with the retro feel of this house, it's straight out of the 1980's, and has kept that charm over the years. We have consistently updated it with all of the amenities needed to relax, including Air Conditioning, High Speed wifi, Cable, big screen TV and sound bar.

Country Colonial Home with rolling fields & stream
This wonderful colonial home offers wide open space on 21 acres of rolling fields with paths leading to the Green River. In the summer build your own dam or in the winter cross country ski along the edges of the stream and get a full view of the West Arlington valley. Swearing Hill is located within a mile of an old country store for all types of immediate supplies. The town of Arlington is 5 miles away, and Manchester, Vt. Is 14 miles, offering golfing, shopping, and wonderful restaurants.

Modern Cabin with Hot Tub & EV Charging Station
Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Charming Vermont Schoolhouse
Kick back and relax in this calm, stylish space. A beautifully restored schoolhouse circa 1860 welcomes you. Situated on a quiet country road this adorable home on one wooded acre has lovely mountain views and a peaceful setting. Nearby you will find skiing, hiking trails and quaint Vermont towns with shops and restaurants. Manchester and Rutland are 30 min. drives, Dorset is just 20 min. Granville NY has a large grocery store and other shops and is only a 15 min. drive.

Modern 3-bedroom A-frame in Londonderry w/ Pond
This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

Wild Blossom Farmhouse - a lovely family getaway
Welcome to Wild Blossom Farmhouse! Conveniently located near Magic, Bromley, Stratton, and Okemo! At our little piece of Vermont, you will find farmhouse-style decor and furnishings, beautiful bright daytime light, and a delightful garden complete with treehouse, tree swing, and fire pit! ***Longterm Stays Allowed*** Four-legged friends welcome with an additional $75 per pet fee.

Stunning mid-century house on 2.5 private acres
Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.
Popular amenities for Weston house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Magical Farm Getaway - a must visit!

The 1770 House

Steps to Golf and Mountain Biking

Ranch at Mendon Mt Orchards

Adams Farm-"The Little Farmhouse"

The Brick House on Washington Street

Classic VT Ski Chalet - Walkable to Okemo Ski Lift
Weekly house rentals

Cozy Modern Sugar House with spectacular views.

CozyDen - AC, Grill, Bike to Mountain, Porch!

The Post Haus: one-of-a-kind modern VT experience

Stunning Okemo Views - 3BD 3BA on 10 Private Acres

Comfortable farmhouse with stunning views

One Room School House. No Cleaning Fees!

Killington Retreat | Deck-Fire Pit-Mountain Views!

Stylish Vermont Cabin | Views · Trails · Luxe
Private house rentals

6 Bed 6 Bath | Hot Tub | Arcade | 16 min Okemo

Modern cabin close to all mountains

Luxury VT Retreat. Breathtaking Views & Sunsets

Green Mountain Carriage House

Stunning 3 br Timber Frame ski retreat on 6 Acres

The Looking Glass, a modernistic escape

Vermonts Best Cabin at Trail End Ranch

Cozy private cabin near Okemo! Large Hot tub!
When is the best time to visit Weston?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$80,156 GYD | G$84,969 GYD | G$78,063 GYD | G$61,529 GYD | G$60,064 GYD | G$65,296 GYD | G$69,901 GYD | G$60,692 GYD | G$60,483 GYD | G$64,669 GYD | G$72,621 GYD | G$77,016 GYD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Destinations to explore
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- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Berkshire East Mountain Resort
- Stratton Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Killington Resort
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- Dartmouth College
- Ragged Mountain Resort
- Fort Ticonderoga
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Montshire Museum of Science
- Mount Sunapee Resort
- Emerald Lake State Park
- Massachusetts Museum of Contemporary Art
- Mount Monadnock
- Trout Lake





