Pet-friendly holiday rentals in Bennington

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

Outdoor spaces · Walkability · Nearby

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

Pets · Outdoor spaces · Checkout

The Farm Cottage- Quiet 1BR on Hobby Farm

Welcome to our peaceful 1-bedroom cottage on a small hobby farm, perfect for couples or solo travelers visiting the Bennington area. This cozy space is designed for rest and simplicity. Whether you're in town visiting family, exploring local trails, or just passing through for a few days, you’ll have a comfortable place to unwind and recharge. Thoughtful touches like fresh eggs from our chickens and homemade jams await you, while the cozy setup makes it easy to settle in and feel at home.

Walkability · Outdoor spaces · Checkout

Warm Brook Farm | Farmhouse & Gardens | Hot Tub

Step into the timeless charm of Warm Brook Farm, a beautifully restored 18th-century farmhouse in Southern Vermont. Once a lively inn and stagecoach stop in the early 1800s, this elegant retreat combines historic character with modern luxury. Enjoy a genuine chef's kitchen, award-winning gardens, and upscale amenities throughout. We cover your Airbnb service fees — the price you see is what you pay. An inviting getaway to relax, explore, and create lasting memories with family and friends.

Outdoor spaces · Pets · Kitchen

Cozy VT Barn • Fireplace + Fall Foliage+All Season

Unwind in a one-of-a-kind renovated Vermont barn set on large property, where vintage charm meets cozy comfort. A Guest Favorite, this unique retreat is perfect for families, friends, couples, holiday stays, and year-round Vermont getaways. The Barn features 2 private bedrooms plus an additional upstairs sleeping area, with plenty of room to relax and reconnect. Cozy up by the fireplace, gather around an outdoor campfire, or simply enjoy the mountain surroundings and sounds of the brook.

Walkability · Pets · River

Guest Cottage - Mountain Views, History & Hiking

Stay in a newly renovated cottage in the heart of Old Bennington, at the oldest frame house in Vermont! Overlooking a 3-acre yard with mountain views, enjoy New England foliage/skiing/hiking and history steps away. The Bennington Monument, First Church, Robert Frost's grave, and the Bennington Museum are 2 mins away, as are Bennington restaurants and shopping. Williamstown, North Adams museums, Manchester shopping and nordic and downhill skiing are all within a scenic 20-25 min drive.

Pets · Outdoor spaces · Kitchen

Quaint One-Story Vermont House with Mountain View

From our quaint one-story house, you can see a variety of scenery, from the bright changing colors of the leaves in the autumn to the soft piles of snow in the winter. Experience the quiet of the nearby woods, and see roaming animals such as deer or turkey. Make sure to stop at one of the nearby lakes, each of which offers a variety of amenities, and lush scenery. In the winter, keep warm in the cozy living room next to the fireplace, while having a chat with your friends and family.

Pets · Outdoor spaces · Family

5BR Rustic Mountain Sanctuary Dome Home

Find connection in this secluded mountainous retreat. Enmeshed in the natural landscape, this space is only accessible via unpaved roads. Even the journey here is part of the adventure. *4WD & Snowtires are needed during winter & early spring due to the possibility of snow or mud* This property requires a lot of upkeep and the steward will likely be onsite during your stay, however the whole house will be exclusively reserved for your booking. This space will rejuvenate & inspire

Outdoor spaces · Pets · Backyard

**Happy Hour! Gorgeous & Modern Downtown Retreat**

Come enjoy our beautiful apartment above our liquor store in downtown Wilmington! Lots of local shops and dining right in town! We are along a river and next to a hiking trail system! Walking distance to the serene 10+ mile lake; kayaks, stand-up paddle boards or motor boat/jet ski rentals nearby. In the winter, enjoy local trails on snowshoes or cross-country skies; only 15 minutes to Mount Snow! We look forward to meeting you!!!

Outdoor spaces · Walkability · Family

The Vermont Farmhouse|Hiking|Dog Trails|Village

The Luxury of Slowing Down — Vermont Style. Leave the rush behind and feel rested, reconnected and renewed at our dog-friendly, beautifully restored 1860s farmhouse. Wide-plank floors, sun-filled rooms and modern comforts create a warm, impeccably clean retreat. Walk across the road into 280 acres of peaceful Mile Around Woods trails, or stroll into historic North Bennington for cafés and shops. It's all right at your doorstep.

Pets · Walkability · Kitchen

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Escape to the serene beauty of Vermont's Green Mountains at the Mount Snow Chalet, a charming retreat nestled on a private wooded lot in the desirable Chimney Hill community of Wilmington. 🏠🌳 Just minutes from the slopes of Mount Snow, our chalet offers the perfect blend of rustic charm and modern amenities for an unforgettable getaway. Designed with love and care, we invite you to relax and stay awhile! 🥰

Pets · Walkability · Location

White Rock Farm

White Rock Farm is a working sheep farm in Bennington VT, part of the scenic and historic Valley of Vermont and surrounded by the Green and Taconic Mountains. The farm is a place where successive generations have been stewards of its 295 acres. First established in 1828, today it remains a working farm that includes livestock, maple syrup, and timber production.

Pets · Outdoor spaces · Decor