Pet-friendly vacation rentals in Windham

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

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!

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

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)

Riverbed Treehouse @hot tub & a new sauna & views!

The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

10 min from Stratton! Log Cabin w/ Beautiful Views

Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!

The Woodland A-Frame

Welcome to The Woodland A-Frame! Built in 1965, our cozy cabin is located 20 mins from Stratton Mountain & Mt. Snow, and 30 mins from Bromley, & Magic Mountain! Vermont is a four-season state, allowing guests to enjoy the cabin anytime of year. Whether it's for fall foliage, winter activities, spring festivals, or a summer at the lake, we are happy to host you anytime during the year to experience your ideal Vermont getaway! Dogs welcome with a $100 pet fee per pet (two dog max). No cats

Designer Chalet w/ Mountain Views close to it all

A perfect little getaway. This stylish 3 bedroom/2 bath chalet is surrounded by endless outdoor activities. Swimming, hiking, biking, visiting the local waterfalls, golf courses, or rent an ATV from local outfit. This beautiful home is perfect for 6-8 people. Situated on 2.5 acres, this private setting with mountain views, has everything you need to feel at home. Multiple restaurants, cafes, markets for food, beer & wine less than a 5 min drive as well to sporting stores for supplies.

Luxury “Tiny” House With Sauna (Timbery)

The Timbery: This is a new, fully handmade, timber frame "tiny" house featuring a custom Norwegian Sauna. The house is nestled in the forest, accessible by foot. With 17 vertical ft. of floor to ceiling windows, this property represents a unique experience to fully immerse yourself into nature. It is like lying down in a tent on the forest floor, except instead of wet sleeping bags and dirty hair, you enjoy a queen sized bed, in home theater, full kitchen, sauna and 71in soaking tub.

Classic Vermont A-Frame | Fire Pit | Near Stratton

Escape to a classic Vermont A-Frame in Jamaica, Vermont on a private wooded 3-acre property along scenic Route 100. Near Stratton Mountain, Mount Snow, Jamaica State Park, and Pike Falls, this peaceful mountain retreat is perfect for hiking, swimming holes, fall foliage, scenic drives, and outdoor adventures. Enjoy mornings on the screened porch and evenings around the fire pit listening to the river across the street under the Vermont stars.

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).

Quaint stone house!

⭐️ 2022 Rockingham Old House Award ⭐️ Take it easy at this unique and tranquil getaway. The Cairn of Vermont is an 1840s stone house located in the sleepy remnants of Bartonsville Village, now part of Chester, VT. 20 minutes to skiing and hiking, biking and the great outdoors are all around you! Less than 5 minutes to Vermont Country Store and make your way home through the Bartonsville Covered Bridge!