Holiday rentals in Weston

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.

4.95 out of 5 average rating, 324 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!

4.98 out of 5 average rating, 256 reviews

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

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.

4.99 out of 5 average rating, 156 reviews

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

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

4.96 out of 5 average rating, 116 reviews

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

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

4.99 out of 5 average rating, 105 reviews

The exterior of a two-story house is depicted, featuring a welcoming entrance with wooden steps and a green door. Window boxes with plants are positioned below each window on the light gray facade, surrounded by a landscaped yard with a gravel pathway leading to the front door.

Flat in Londonderry

Bread and Butter Apartment

Our house is located just a few minutes from Magic Mountain and less than thirty minutes from Bromley, Stratton and Okemo. Chester and Londonderry are a short drive away, and there are many wonderful hikes nearby. The apartment occupies the entire second floor of our house and has a private entrance. It includes two cozy bedrooms, a 3/4 bath, a small kitchen and a comfy living room. The apartment still has that old Vermont charm and is perfect for a relaxed weekend in the Green Mountains.

4.96 out of 5 average rating, 119 reviews

Tiny home in Ludlow

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

5.0 out of 5 average rating, 82 reviews

The living room showcases vaulted wooden ceilings and large windows offering expansive views of the outdoors. A cozy seating arrangement is positioned around a central coffee table, with warm lighting provided by a chandelier. Natural light fills the space, enhancing the welcoming ambiance.

Home in Andover

Luxury VT Retreat. Breathtaking Views & Sunsets

Mountain views, unforgettable sunsets and seamless indoor - outdoor living, this fully renovated Vermont retreat is all about the view. Cozy up by the wood-burning fireplace, cook in a custom kitchen, and relax on the spacious deck under the stars. Set on 4 private wooded acres just 15 minutes from Okemo, this 3-story home offers peace, privacy, and pure Vermont charm — perfect for family getaways, romantic escapes, or outdoor adventures. fully remodeled top to bottom.

4.99 out of 5 average rating, 155 reviews

An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.

Home in Londonderry

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). STR License 26-23-185

4.87 out of 5 average rating, 120 reviews

Cozy Vermont Mountain Escape near Okemo & Stratton

Welcome to Windsor Springs - an iconic 4-bedroom Vermont mountain retreat nestled on 4+ private wooded acres just minutes from Okemo, Stratton, Magic Mountain, and historic downtown Weston. Whether you're hitting the slopes, exploring 4,700+ miles of VAST snowmobile trails right from the backyard, or taking in peak autumn foliage, Windsor Springs offers the perfect blend of nostalgic 1980s charm and high-end modern comfort.

The chalet's exterior is showcased with a sloped metal roof and large glass windows. A spacious wooden deck extends from the living area, featuring outdoor seating options. Surrounding greenery and a stone pathway enhance the natural setting, creating a tranquil atmosphere.

5.0 out of 5 average rating, 25 reviews

Modern cabin close to all mountains

Nestled in the heart of Southern Vermont, this cozy, modern chalet offers the perfect winter getaway. The house is near Magic Mountain (5 miles), Bromley (10mi), Stratton (15mi), and Okemo (15mi). With sprawling windows that bring the outdoors in, it enjoy a luxury kitchen, stylish design, and plenty of privacy. When you’re not on the mountains—groceries and dining are minutes away.

4.97 out of 5 average rating, 481 reviews

A bright interior is featured, showcasing a mix of seating options including a blue sofa and an upholstered armchair. A small dining table is complemented by wooden chairs. The kitchen area is visible, equipped with diverse utensils, while large windows on two sides allow natural light to fill the space.

Flat in Andover

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

4.91 out of 5 average rating, 423 reviews

An open layout studio space showcases a modern kitchenette against a neutral backdrop. The area features a cozy seating arrangement, an electric fireplace, and ceiling fans, while wood accents and flooring add warmth to the ambiance.

Flat in Londonderry

Cozy Suite in a Historic Building Near Ski Resorts

Located on the second floor of a historical building in the Village of South Londonderry, Vermont, this renovated studio suite features unique touches of modern amenities but with a Vermont feel. Your room will include a 65 inch Smart TV, WiFi, electric fireplace, lush queen bed, full renovated bathroom, small kitchenette, as well as on site parking.

Popular amenities for Weston holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Weston

Superhost

The living area features a large brown leather sectional sofa facing a brick fireplace. A glass coffee table sits on a decorative area rug, surrounded by two red stools. The open kitchen can be seen in the background, with wooden cabinetry and bar seating under bright overhead lights.

4.78 out of 5 average rating, 46 reviews

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

4.95 out of 5 average rating, 42 reviews

An updated church building features a blend of shingle siding and architectural details. Large arched windows are visible, along with a distinctive spire above the entrance. Snow covers the surrounding area, which is framed by trees and a clear blue sky.

Home in Londonderry

The Green Mountain Chapel

5.0 out of 5 average rating, 8 reviews

Farm stay in Weston

3 bdrm Stillwater Farmhouse near 4 ski resorts

Superhost

4.88 out of 5 average rating, 8 reviews

Cottage with a view in Weston

5.0 out of 5 average rating, 55 reviews

West River Farmhouse in Weston, VT

4.98 out of 5 average rating, 63 reviews

A warm, wooden exterior of a cabin-style home is highlighted, featuring a front porch with seating and a sloped roof. Surrounding trees reflect the changing colors of autumn, contributing to a serene outdoor setting.

Home in Mount Holly

Cozy 2 bedroom house, close to Okemo & Killington