Vacation rentals in Weston

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Top-rated vacation rentals in Weston

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Top guest favorite
Icicles hang from a ledge, glistening in the sunlight. The backdrop features rolling mountains with patches of snow and a clear blue sky, creating a serene winter landscape visible through the ice formations.
Guest suite in Weston
4.98 out of 5 average rating, 244 reviews

Spacious King Spa Suite Weston Hills

Spacious 750 sqft guest suite king bed, table & chairs, kitchenette & sitting area & large, private spa bathroom featuring walk through mosaic shower area 4 shower heads, jets, wands & two person roman jacuzzi tub featuring aroma & chroma therapy & heated back rests. Ensuite bidet, elongated toilet & urinal. Pull-out sofa & comfy king bed with views from 5 glass doors to private deck. Xfinity high speed Internet and streaming TV. Private entrance from deck or shared entrance via front door.

Guest favorite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry
4.95 out of 5 average rating, 245 reviews

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Top guest favorite
The exterior of a two-story contemporary home is depicted, featuring green-framed windows and a pathway lined with gravel. Adjacent grassy areas and trees create a natural setting. A blue flag flutters near the entrance, enhancing the welcoming feel of the property.
Home in Weston
4.96 out of 5 average rating, 312 reviews

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!

Top guest favorite
A spacious living area features a central stone fireplace, surrounded by cozy seating. Large windows frame scenic views of the trees outside, filling the space with natural light. The rustic wooden beams and walls add warmth, while the open layout connects to the kitchen and loft above.
Barn in Andover
4.99 out of 5 average rating, 148 reviews

Fat Cat Barn - Close Okemo & Magic, Vermont

Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

Guest favorite
A spacious living room features a textured red carpet and a large beige sectional sofa, complemented by a wooden coffee table. A stone fireplace is situated against one wall, with large windows providing views of the surrounding greenery. Decorative plants and artwork enhance the inviting space.
Home in Weston
4.87 out of 5 average rating, 120 reviews

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.

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 362 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favorite
The rustic cabin sits amidst a lush green landscape, framed by towering trees. The stone chimney adds character, while the two separate structures showcase a combination of wood siding and modern roofing. Clear blue skies create a serene backdrop for the natural beauty.
Cabin in Landgrove
4.99 out of 5 average rating, 214 reviews

The Owl’s Nest in Landgrove

Our recently renovated cabin is the perfect escape during any season! Located within minutes of Bromley, Magic, and Stratton, Wild Wings, and Viking. Also nestled in an amazing network of hiking, biking and ski trails. Guests will never be more than a few minutes away from outdoor adventure. With two bedrooms and one bonus loft, guests can enjoy the comforts of our cozy cabin, including a full kitchen, bathroom, outdoor shower, HOT TUB, fire pit, WiFi and FREE EV CHARGING. @owlsnestvt

Superhost
An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.
Cabin in Mount Holly
4.87 out of 5 average rating, 160 reviews

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

Top guest favorite
An elevated deck is softly illuminated by hanging lights, featuring a hot tub and a panoramic barrel sauna. Snow covers the ground, and the landscape is filled with distant hills under a twilight sky, creating a serene outdoor retreat.
Cottage in Shaftsbury
4.98 out of 5 average rating, 759 reviews

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Superhost
A modern cabin features a contrasting black exterior and wooden accents, nestled among lush trees. A wide deck with railing leads to the entrance, offering a welcoming space to enjoy the surrounding nature. Large windows provide ample natural light and views of the forest.
Tiny home in Athens
4.86 out of 5 average rating, 172 reviews

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

Guest favorite
Chalet in Peru
4.83 out of 5 average rating, 109 reviews

A-Frame | Floor-to-Ceiling Windows, Bromley 1mi

Floor-to-ceiling windows, soaring wood-paneled ceiling, and a natural brook outside the door. Classic Vermont A-Frame on a quiet gravel road in Peru — 1 mile from Bromley Mountain and the Appalachian Trail. King master with its own fireplace and French doors to the backyard. Living room fireplace, renovated kitchen and baths, lofted twin bedroom. Fast WiFi. Superhost Michael, 5.0 communication rating.

Top guest favorite
A patio area is visible, featuring a stone fire pit with colorful glass accents. Comfortable seating is arranged around the fire pit, with a large umbrella providing shade. The expansive green landscape stretches in the background, offering a view of distant mountains under a cloudy sky.
Apartment in Weathersfield
4.97 out of 5 average rating, 151 reviews

Cute VT Bungalow With 180 Degree View of NH

Located on a quiet country dirt road you will find this cozy apartment perfect for a weekend getaway. A short walk and you will be amazed at the 360 degree views of Vermont and New Hampshire. Centrally located near Okemo, Sunapee and Killington mountains, ski all 3 mountains in a weekend. Explore covered bridges, walking trails, scenic bike rides, or tubing on the Connecticut River.

Popular amenities for Weston vacation rentals

When is the best time to visit Weston?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$62,658 GYDG$75,816 GYDG$60,151 GYDG$52,424 GYDG$48,455 GYDG$45,740 GYDG$63,284 GYDG$47,620 GYDG$60,360 GYDG$61,822 GYDG$69,968 GYDG$76,860 GYD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Weston?

    Weston has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Weston?

    Experience the best of Weston with our house rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Weston?

    Four-legged friends are welcome in Weston. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Weston?

    Yes! Work meets play with ease at over 40 vacation rentals in Weston featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Weston have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Weston. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Weston have a kitchen?

    Absolutely! We offer over 40 house rentals with a kitchen in Weston. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Weston have wifi?

    Absolutely! We offer over 40 house rentals with wifi in Weston. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Weston have free parking?

    Absolutely! We offer over 10 cabin rentals with free parking in Weston. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Weston

  • Total vacation rentals

    Explore 60 vacation rentals in Weston

  • Nightly prices starting at

    Weston vacation rentals start at G$20,886 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,250 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Weston vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Weston rentals

  • 4.9 Average rating

    Weston stays are highly rated by guests—averaging 4.9 out of 5!

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