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Pet-friendly holiday rentals in Bennington County

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Bennington County

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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Superhost
The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.
Cabin in Wardsboro

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Outdoor spacesPetsAir conditioning

4.87 out of 5 average rating, 193 reviews
Top Guest favourite
Cabin in Stratton

Log Cabin King Beds AC Near Hike Bike Swim Golf!

Kick back and relax in this calm, stylish, newly built log cabin which was finished in early 2022. Fully equipped with stainless steel appliances, soapstone counters, central a/c, all new furniture, mattresses and bedding. First floor master bedroom leads into a large, covered, screened in porch, which is perfect for your early morning coffee or evening cocktails. Starlink high speed Wi-Fi and a smart tv in the living room and bedroom. 7 Minutes from Stratton Mtn, 15 from Mt Snow. Nearby lakes!

PetsOutdoor spacesAccess

5.0 out of 5 average rating, 204 reviews
Top Guest favourite
The exterior of a charming yellow farmhouse is surrounded by lush gardens filled with vibrant flowers. An outdoor kitchen area is equipped with stainless steel grills, while a cozy fire pit area features wooden seating, inviting guests to enjoy warm evenings amidst the rich greenery.
Home in Arlington

Warm Brook Farm | Autumn Foliage | 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.

PetsOutdoor spacesLocation

5.0 out of 5 average rating, 141 reviews
Top Guest favourite
Farm stay in Bennington

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.

WalkabilityPetsBackyard

4.98 out of 5 average rating, 265 reviews
Guest favourite
A charming exterior view of the house is displayed, featuring a welcoming entrance with a front porch and wooden steps. The property is flanked by a two-car garage, with a gravel driveway leading up to the house. Lush greenery surrounds the building, providing a sense of seclusion.
Home in Manchester

Ski and Play in Manchester Center!

Fully renovated 2000 sf 5 bedroom/2 bathroom house in the heart of Manchester Center, VT! 6 miles to Bromley, 15 miles to Stratton, 6 miles to the Vermont Summer Festival horse show, and less than a mile to all of the shops and restaurants Manchester Center has to offer! You cannot beat this location no matter the season! The house is set back off the road and surrounded by woodlands so even with all of these amenities at your fingertips, you feel like you're far off the beaten path!

WalkabilityOutdoor spacesBathroom

4.95 out of 5 average rating, 136 reviews
Top Guest favourite
A charming two-story cabin features natural wood siding and a welcoming front porch. Lush green landscaping surrounds the home, and tall trees provide shade. A stone pathway leads from the driveway to the entrance, enhancing the connection to the serene outdoor environment.
Home in Sunderland

MOUNTAIN NEST, views, Manchester, hot tub,

Convenient to downtown Manchester's outlet stores and restaurants,golf (equinox golf course 3 miles away) hiking, kayaking and fishing (battenkill river)skiing-Stratton or Bromley, hot tub on full deck with close-up views of Mount Equinox, these mountain views will either make you weep or sing for joy, dines 8 easy, master on main (king bed). This home was intended to bring INSIDE the natural beauty you see OUTSIDE. Complete with vaulted living area and exposed timber beams throughout!

PetsOutdoor spacesIndoor spaces

4.97 out of 5 average rating, 284 reviews
Top Guest favourite
A cozy living room features a brick fireplace as a central focal point, complemented by colorful seating arrangements on a warm-toned floor. A small table with a decorative tablecloth displays a notepad and pine cones. Natural light streams through large windows, creating a welcoming ambiance.
Home in Shaftsbury

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.

WalkabilityPetsIndoor spaces

4.88 out of 5 average rating, 155 reviews
Top Guest favourite
A charming log cabin is surrounded by vibrant autumn foliage, showcasing a dark wooden exterior and a sloped green roof. The mountains in the background provide a scenic view, enhancing the peacefulness of the property, which is set on a gravel driveway.
Cabin in Sunderland

The Birchwood Cabin - Stunning Mountain Views

Welcome to the Birchwood Cabin - a beautiful log cabin with stunning mountain views! Relax in the hot tub overlooking the mountains or enjoy hot chocolate by the fire. Play a game of pool or shuffleboard downstairs. The Birchwood Cabin is in a peaceful, quiet location but is only a 10-minute drive to Manchester, if you'd like to go shopping or grab a bite to eat! Hit the slopes at Bromley Mountain or Stratton Mountain or in the warmer weather head to The Equinox for a round of golf!

PetsOutdoor spacesAccess

4.99 out of 5 average rating, 163 reviews
Top Guest favourite
An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.
Home in Londonderry

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

WalkabilityOutdoor spacesWi-Fi

4.99 out of 5 average rating, 155 reviews
Top Guest favourite
The chalet is set against a backdrop of trees, showcasing a combination of natural stone and wood siding. Multiple outdoor seating areas are visible, featuring colorful chairs with a fire pit nearby. Dim evening light gently illuminates the home, highlighting the windows and inviting ambiance.
Chalet in Jamaica

Designer Chalet w/ Mountain Views close to it all

Private 3-bedroom, 2-bath chalet on 2.5 peaceful acres with beautiful mountain views. Comfortably sleeping 6 guests, it’s the perfect Vermont escape for ski weekends, foliage trips, outdoor adventure, or simply relaxing with family and friends. Enjoy nearby hiking, biking, swimming, waterfalls, golf, and scenic drives. Close to Jamaica State Park, Bondville, Stratton, and Mount Snow, with Manchester’s shopping and dining an easy day trip away.

WalkabilityPetsWi-Fi

4.98 out of 5 average rating, 113 reviews
Top Guest favourite
Apartment in Bennington

Suite Sunset 311 Rice Lane Bennington VT

Pet friendly ( additional charge ) Close to picturesque downtown Bennington and many restaurants and attractions. Located in southwest Vermont with easy access to nearby New York and Massachusetts. The famous Bennington Battle Monument provides a free landmark to visit. Enjoy nearby hiking trails and natural areas. Situated on fifty very private acres. Very quiet and peaceful setting. Less than one mile from Bennington College.

PetsWalkabilityTV

4.97 out of 5 average rating, 122 reviews
Top Guest favourite
A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.
Home in Bennington

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.

PetsWalkabilityBackyard

5.0 out of 5 average rating, 138 reviews

Popular amenities for Bennington County pet-friendly home rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Guest favourite
A sunroom is featured with large windows allowing natural light to fill the space. Wooden furniture adds a warm touch, while a woven rug covers the floor. A small side table is positioned next to a seating area, overlooking a green landscape outside.
Home in Manchester

The Equinox Cottage

Outdoor spacesWalkabilityAir conditioning

4.78 out of 5 average rating, 252 reviews
Guest favourite
The spacious interior features rustic wooden beams and an open layout that connects the kitchen and living area. A large window offers natural light and views of the outdoors, while a cozy sofa and a striped blanket add warmth. A staircase leads to the upper loft.
Home in Shaftsbury

Cozy VT Renovated Barn + Fall+All Season Get Away

PetsWalkabilityAmenities

4.91 out of 5 average rating, 128 reviews
Guest favourite
Home in Manchester

Picture Postcard Mansion in Manchester Village

WalkabilityOutdoor spacesHeating

4.88 out of 5 average rating, 138 reviews
Superhost
A welcoming living area features a stone fireplace with a warm fire glowing inside. Wooden beams cross the ceiling, and a red couch is complemented by leather ottomans. A large window reveals a snowy outdoor setting, while a coffee table holds various items.
Home in Winhall

The Mushroom House of Manchester Vermont

PetsWalkabilitySkiing

4.85 out of 5 average rating, 205 reviews
Top Guest favourite
A rustic red barn-style home is surrounded by lush greenery, with colorful flowers framing a slate path leading to the entrance. Outdoor seating areas are visible, including a picnic table and lounge chairs, under a vibrant sky painted by sunset hues.
Home in Shaftsbury

Converted Vermont Barn on 6.5 acres with hot tub

WalkabilityOutdoor spacesBackyard

4.94 out of 5 average rating, 159 reviews
Guest favourite
The cabin is set back from the winding gravel driveway, surrounded by lush green grass and trees. Brightly colored autumn foliage adds a touch of warmth against the rustic brick exterior and red roof. The peaceful atmosphere is enhanced by natural surroundings.
Home in Wilmington

Secluded cabin on brook near skiing and lakes

Outdoor spacesPetsBeach

4.86 out of 5 average rating, 104 reviews
Top Guest favourite
A spacious bedroom is illuminated by natural light from multiple windows. A large bed with patterned linens is centered on a wooden floor. A simple chair and framed artwork add to the room's welcoming ambiance, complemented by warm wall tones and soft area rugs.
Home in Manchester

Modern meets Country Cottage in Manchester Village

Outdoor spacesPetsSleep quality

4.96 out of 5 average rating, 141 reviews
Guest favourite
A serene path meanders through lush green grass, leading to a charming farmhouse surrounded by trees. The clear blue sky and gentle clouds create a peaceful backdrop, enhancing the natural setting of the property.
Home in Whitingham

Vermont lake house near Mt. Snow-fab 360 views!

WalkabilityOutdoor spacesFamily

4.91 out of 5 average rating, 122 reviews

Pet-friendly home rentals with a pool

Top Guest favourite
Chalet in Wilmington

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Outdoor spacesPetsKitchen

5.0 out of 5 average rating, 131 reviews
Guest favourite
A rustic log cabin features a porch with seating arrangements, including Adirondack chairs. The front yard is partially landscaped with small plants. Stacked firewood is visible next to the cabin, and the structure is surrounded by trees and greenery, providing a natural, secluded setting.
Cabin in Wardsboro

Log Cabin Near Stratton/Mt Snow

Outdoor spacesWalkabilityKitchen

4.79 out of 5 average rating, 279 reviews
Guest favourite
A large outdoor pool is surrounded by a wooden deck with lounge chairs and umbrellas. The background features a multi-story building with expansive windows. Vibrant autumn trees with colorful foliage frame the scene, providing a serene and inviting atmosphere.
Home in Wilmington

Family-friendly 4BR | Pools Hot Tub | Near Mt Snow

WalkabilityOutdoor spacesHospitality

4.89 out of 5 average rating, 183 reviews
Guest favourite
A spacious ski home is surrounded by snow-covered trees, featuring a modern design with a sloped metal roof. Large windows allow natural light to enter, while a gravel driveway leads to the entrance. This bustling wooded area provides a serene backdrop during winter.
Home in Peru

Beautiful Bromley/Manchester VT Retreat w/hot tub

PetsOutdoor spacesHiking

4.9 out of 5 average rating, 184 reviews
Guest favourite
A rustic log cabin is set amidst lush greenery, framed by tall trees. A covered porch extends along the front, providing space for seating. Natural stone steps lead up to the entrance, and a small fire pit is visible in the foreground, surrounded by stones.
Cabin in Wardsboro

Leonard’s Log - Private Hot Tub, Fire Pit, A/C

PetsOutdoor spacesHospitality

4.92 out of 5 average rating, 223 reviews
Guest favourite
A spacious log cabin home is showcased amidst a lush green landscape. The A-frame structure features large windows allowing natural light to enhance the interior. The wrap-around deck provides outdoor space for relaxation, while steps lead down to an area with garage access.
Cabin in Wardsboro

Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow

Outdoor spacesWalkabilityHeating

4.9 out of 5 average rating, 250 reviews
Guest favourite
Chalet in Winhall

4BR Ski Chalet | Hot Tub | Mins to Stratton, VT

Outdoor spacesPetsParking

4.89 out of 5 average rating, 135 reviews
Guest favourite
A red barn-style house is nestled among autumn trees with vibrant yellow and orange leaves. It features white-framed windows and a covered storage area nearby. The setting conveys a serene environment, inviting guests to enjoy the natural beauty surrounding the property.
Home in Wilmington

The Vermont Barn (Mount Snow)

Outdoor spacesWalkabilityLocation

4.84 out of 5 average rating, 183 reviews

Private, pet-friendly home rentals

Top Guest favourite
A cottage elevated on a hillside is surrounded by autumn foliage. It features a large wooden deck with multiple seating options, providing views of the lush landscape. Beneath the deck, stone walls create a terraced garden, and a blue tarp is visible on the ground.
Cottage in Dorset

Pond Cottage

PetsOutdoor spacesCleanliness

4.97 out of 5 average rating, 190 reviews
Guest favourite
The unique dome-shaped structure is composed of iron and cement, surrounded by lush greenery. Large windows create a bright and airy atmosphere, while the greenhouse-style addition at the front enhances the connection to nature.
Dome in Bennington

5BR Rustic Mountain Sanctuary Dome Home

Outdoor spacesPetsIndoor spaces

4.94 out of 5 average rating, 139 reviews
Superhost
The A-Frame chalet is set amidst vibrant autumn foliage, showcasing a wrap-around deck with wooden railings. A balcony extends above, offering a view of the surrounding trees and an inviting outdoor space with seating.
Chalet in Dover

The Mountain A-Frame at Mount Snow

WalkabilityPetsSleep quality

4.86 out of 5 average rating, 319 reviews
Guest favourite
Cabin in Winhall

A frame cabin with Hot tub near Stratton, VT

PetsWalkabilityTV

4.92 out of 5 average rating, 130 reviews
Guest favourite
A charming cottage entrance is depicted with natural wood siding and a small porch area. Soft lighting enhances the ambiance. A friendly dog sits on the gravel path, surrounded by lush greenery, indicating a tranquil forest setting.
Cottage in Jamaica

Cottage-Swim-View-Firepit-7min to Stratton-Dog OK

WalkabilityPetsTV

4.85 out of 5 average rating, 641 reviews
Top Guest favourite
A well-lit kitchen and dining area features a wooden dining table surrounded by six chairs. Light hardwood flooring complements the gray cabinetry. A potted plant sits on the table, and modern appliances are visible in the background, including a refrigerator and stove.
Apartment in Wilmington

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

WalkabilityOutdoor spacesGetting around

4.98 out of 5 average rating, 542 reviews
Top Guest favourite
A deck area features four comfortable chairs surrounding a glass-topped table. Lush greenery and trees with autumn foliage create a colorful backdrop, while a clear blue sky adds to the inviting outdoor setting.
Barn in Manchester

Cozy Barn home w/ Mountain Views

WalkabilityOutdoor spacesDecor

4.98 out of 5 average rating, 132 reviews
Guest favourite
A cozy bedroom features a metal bed frame adorned with a colorful quilt. Soft pillows are arranged at the head of the bed, and a bedside lamp provides gentle illumination. An angled ceiling creates an intimate atmosphere, complemented by a framed landscape picture on the wall.
Guesthouse in Manchester

Romantic Barn Guesthouse in Village Center

PetsOutdoor spacesHeating

4.77 out of 5 average rating, 348 reviews

Destinations to explore