Holiday houses in Weston

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!

Value · Location · Layout

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.

Value · Location · Nearby

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

Location · Value · Cleanliness

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

Family · Location · Long stay

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

Family · Location · Decor

West River Farmhouse in Weston, VT

Our c. 1835 Farmhouse is a comfortable and warm home to base your Vermont adventure. Antique yet updated charm with wide pine floors, beamed ceilings, and cozy stoves. Lovely outdoor space to relax after a day of exploring beautiful Southern Vermont. We are centrally located between four major ski mountains, easy access to hiking the Long Trail, and just down the road from the village center of Weston- home to the famous Vermont Country Store and world class theatre at the Weston Playhouse.

Family · Location · Backyard

Cottage with a view in Weston

Enjoy mountain views and an on-site spring, walking distance from Weston village and within 20 minutes of 3 ski resorts. Located just off scenic Route 100, the home is perfect for leaf peeping. Our spacious cottage has everything your family or group needs for a comfortable stay. Flexible sleeping options with two pull-out sofas. After a day of enjoying all Vermont has to offer, walk to the original VT Country Store then unwind under the vaulted ceilings of the loft room with a game or puzzle.

Location · Family · Comfort

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.

Family · Value · Access

3 bdrm Stillwater Farmhouse near 4 ski resorts

Have you ever wanted to live back in the 1800s in an old farmhouse on 30 acres? We did! Here’s your chance! This is our family home but sometimes we go out of town and are happy to share it with others. It's really like walking back into history except for the comfortable couches in the living room And graciously updated bathrooms and kitchen. You’ll find antique bed warmers, spinning wheels, beautiful lamps, and furniture which will take you back to a more peaceful time.

Family · Location · Pets

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

Location · Family · Breakfast

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.

Location · Value · TV

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.

Location · Family · Access