Pet-friendly vacation rentals in Bennington

Runamuk Farm

Picturesque location on farmland with views of the mountains. We are a micro farm. Wake up and watch the sunrise and go for a short hike on the property, and get to know the animals. We are located 35 minutes from Saratoga Springs and Lake George, NY and 45 minutes from Dorset and Manchester, VT. Hike the Adirondack or Green Mountains, paddle the streams or go to a nearby small city for a play, a festival, or a concert. There is a long list of things to do and see within an hour of our camp.

Outdoor spaces · Pets · Hiking

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 · Check-in

One of Kind renovated Cozy VT Barn +Guest Favorite

Unwind in a stylish “one of a kind" refurbished barn with a cozy and relaxing vintage vibe. Perfect for Family Travel, friends or a couple’s getaway all year long and Holidays. The barn has 2 bedrooms plus an extra sleep area upstairs. Gather in the living room area with the fireplace or enjoy the yard views with a campfire and sounds of the babbling brook. Nearby attractions: swimming, hiking, skiing, fishing, biking, shopping, golf, breweries, museums, restaurants, local or a drive away.

Walkability · Pets · Parks

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

Pets · Outdoor spaces · Family

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 · Walkability · Parking

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.

Outdoor spaces · Pets · Heating

The Vermont Farmhouse|Hiking|Dog Trails|Village

Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

Outdoor spaces · Pets · Comfort

Artistic Nature Cottage

Kalarama Cottage is a newly renovated space in the middle of nature! Make yourself right at home in this quiet, private and peaceful location. The cottage is overlooking a beautiful forested mountain range, with easy access to hiking, biking, and cross-country ski trails right out the door. Kalarama is bright and sunny with stunning views. Come to unwind, enjoy nature, read, meditate or just work remotely from our 23 acre property!

Walkability · Outdoor spaces · Indoor spaces

400+ Airbnb Visits: Incredible Mountain Cabin

Our cabin is off the grid, NO running water (read this twice) or indoor bathroom, but it’s comfortable and has been enjoyed by 100’s of Airbnb travelers. There is electricity, but this cabin takes an adventurer in the winter months. Winter Stays take work! Don’t be surprised of shoveling and bringing in your gear! Our reviews speak for how great rental is for people, thank you for considering a stay at our cabin.

Pets · Walkability · Parks

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! 🥰

Walkability · Pets · Air conditioning

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.

Outdoor spaces · Pets · Indoor spaces

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Please indicate the number of suites you will need (1, 2, or 3).

Walkability · Pets · Beach