Vacation rentals in Weston

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Top-rated vacation rentals in Weston

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
The cabin's exterior showcases a sturdy log design with a grey roof and inviting wrap-around porch. Flowering planters are placed on either side of the door, and two rockers are positioned for outdoor relaxation, surrounded by landscaped gravel.
Cabin in Andover
4.96 out of 5 average rating, 110 reviews

Little Cabin on the Ridge

Classic Vermont cabin.This cozy home is perfect for singles, couples and families.The well-designed space offers sleeping for 4 in two bedrooms and an open loft space. Wrap around porch has 4 rockers for taking in the mountain air, coffee or tea, or reading in a cozy quilt. Fiber optic wifi 1000 mbps.Very efficient forced hot air heating and Central Air cooling.Peaceful, quiet,relaxing, great place to unwind with all kinds of activities nearby. due to health and safety concerns no animals please

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, 245 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
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford
4.94 out of 5 average rating, 133 reviews

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!

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, 250 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, 313 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, 150 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, 371 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, 215 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

Guest favorite
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, 164 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.

Superhost
A wooden walkway extends towards a charming cabin surrounded by dense greenery. The path, lined with black railings, leads to a uniquely designed structure with a peaked roof, enhancing the connection with nature. A simple black chair rests on the adjacent porch.
Tiny home in Athens
4.86 out of 5 average rating, 177 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.

Top guest favorite
A spacious living area features large floor-to-ceiling windows offering a view of the green outdoor space. A plush sofa, accented with colorful cushions, sits in front of a wooden coffee table. A modern dining area is visible in the background, illuminated by soft lighting.
Home in Winhall
4.98 out of 5 average rating, 423 reviews

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 vacation rentals

When is the best time to visit Weston?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR6,215 ZARR6,329 ZARR5,969 ZARR4,105 ZARR3,794 ZARR3,582 ZARR4,955 ZARR3,729 ZARR4,726 ZARR4,841 ZARR5,479 ZARR6,018 ZAR
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

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 cabin rentals in Weston have a kitchen?

    Absolutely! We offer over 10 cabin 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 house rentals in Weston have free parking?

    Absolutely! We offer over 40 house 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 R1,635 ZAR 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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