Family-friendly holiday 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

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

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.

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Vermont Treehouse - Romantic Private Elegant

2 night minimum, self checkin. This romantic, elegant, private getaway for two (or one) in our "Treehouse" with sleeping loft, fully stocked kitchen & bathroom, screened porch, deck, sauna, WiFi, BBQ grill, pond, etc. Overlooking pasture & mountains. Enjoy the property with 3 miles hiking/snowshoe trails. Guest house on 160 acre private horse farm. Lots to do in nearby towns: ski areas, shopping, hiking, biking, theater & music in summer. Or just relax. Discount for longer stays.

Cozy Cabin at Frog Pond Farm

Cozy 500sq ft passive solar cabin on our small farm, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/gardens or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

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.

The Architect's Cabin, on 10 Secluded Acres

Nestled on a rise in a woodland clearing is this intriguing cubist design reminiscent of Post and Beam ambiance. Stone and wood materials from the property have been assimilated into intriguing modern design features throughout. Walls of windows share the tranquil and private outdoor setting with the indoor livings areas. We require all guests have a verified account and positive host reviews. There is no Air Conditioning.

Modern Cabin with Outdoor Spa on Vermont Farm

Romantic modern cabin with private hot tub on a 100-acre Vermont farm. This Scandinavian-style retreat features soaring windows, a king bed with luxury linens, a cozy fireplace, and a sleek kitchen. Perfect for couples seeking a peaceful getaway, farm stay, or eco-friendly escape. Soak under the stars, meet our friendly goats, and enjoy the beauty of southern Vermont from your light-filled solar-powered cabin.

Vermont Getaway Apartment

A 2 bedroom apartment attached to our home, close to Stratton, Bromley, Magic, Okemo & Mt Snow Skiing, hiking, fishing, golfing, tennis, outlet shopping and fine dining all close by. Manchester a short drive. Hot tub available from 8am-8pm. Level 2 EV charger available for a $10 cash fee (and give us advance notice if possible so we can open the garage for you).

The Post Haus - One-of-A-Kind Modern VT Experience

Welcome to The Post Haus! A one-of-a kind, modern Vermont mini cabin in the Green Mountain National Forest. This high-end, mid-century mod getaway offers an indoor wood-burning fireplace, sauna, high-end kitchen, and two acres alongside the beautiful Ball Mountain Brook. Come enjoy our truly special piece of Vermont!

Green Mt Magic - Close to Golfing Tennis Parks

Family-friendly mountain getaway with easy access to the best of what VT has to offer: golf, tennis, parks, dining. Walk to Magic, 15-25m to Bromley, Stratton, Okemo mountain parks. Floor-to-ceiling windows, unmatched 90+ board game library, & home theater for epic family nights in.