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Pet-friendly holiday rentals in Bennington

Find and book unique pet-friendly homes on Airbnb

Quick stats about holiday rentals that are pet-friendly in Bennington

  • Total holiday rentals

    Explore 20 holiday rentals in Bennington

  • Nightly prices starting at

    Bennington holiday rentals start at $140 AUD per night before taxes and fees

  • Verified guest reviews

    Over 600 verified reviews to help you choose

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Bennington holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Bennington rentals

  • 4.8 Average rating

    Bennington stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated pet-friendly home rentals in Bennington

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

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Guest favourite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry

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 spacesPetsCheck-in

4.95 out of 5 average rating, 270 reviews
Top Guest favourite
Cabin in East Nassau

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!

Outdoor spacesPetsAmenities

4.97 out of 5 average rating, 109 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.

Outdoor spacesPetsHospitality

4.98 out of 5 average rating, 264 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 | 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.

PetsOutdoor spacesQuiet

5.0 out of 5 average rating, 140 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

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.

Outdoor spacesWalkabilityCondition

4.91 out of 5 average rating, 128 reviews
Top Guest favourite
A light-filled kitchen features modern appliances, including a vintage-style refrigerator. White cabinetry complements a wooden countertop. The open layout connects to a living area, where a cozy blue chair adds a pop of color. Large windows allow natural light to brighten the space.
Guesthouse in Bennington

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.

PetsOutdoor spacesNearby

4.99 out of 5 average rating, 103 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.

WalkabilityPetsWi-Fi

4.88 out of 5 average rating, 155 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

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

PetsOutdoor spacesValue

4.93 out of 5 average rating, 138 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!

Outdoor spacesPetsLocation

4.99 out of 5 average rating, 162 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.

WalkabilityPetsGetting around

4.97 out of 5 average rating, 121 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.

Outdoor spacesWalkabilityQuiet

5.0 out of 5 average rating, 138 reviews
Top Guest favourite
Yurt in Dover

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Seven minutes from the Mount Snow lifts, this creekside yurt turns mountain days into sauna nights. Ski, hike or explore Southern Vermont, then soak in the private hot tub, heat up the cedar sauna and settle in by the wood stove. The soaring dome, pool table, PS5, stocked kitchen and pet-friendly setup make it an easy year-round base for couples, families and friends.

Outdoor spacesPetsLong stay

4.93 out of 5 average rating, 137 reviews

Popular amenities for Bennington pet-friendly home rentals

Pet-friendly house rentals

Pet-friendly home rentals with a pool

Top Guest favourite
Chalet in Wilmington

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Outdoor spacesWalkabilityBackyard

5.0 out of 5 average rating, 131 reviews
Top Guest favourite
A clear view of a fenced swimming pool is surrounded by lush greenery and trees. A stone pathway leads to the pool area, with well-maintained flower beds in the foreground. Seating options are available near the pool for relaxation.
Cottage in Averill Park

Cozy cottage with pool, walking distance to lake

PetsWalkabilityCheck-in

4.95 out of 5 average rating, 171 reviews
Top Guest favourite
An aerial view of the property showcases a spacious backyard featuring an in-ground pool, accompanied by a hot tub and lounge seating. The home, surrounded by lush greenery, displays a charming exterior with multiple windows and patio space, ideal for outdoor relaxation.
Home in Saratoga Springs

Saratoga Fall Escape | Hot Tub, Fire Pit & Game Rm

Outdoor spacesPetsFamily

5.0 out of 5 average rating, 104 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

PetsWalkabilityParks

4.79 out of 5 average rating, 279 reviews
Top Guest favourite
The classic two-story farmhouse features white siding with black shutters. A green door welcomes visitors, while lush greenery and blooming lilac bushes create a natural frame. The surrounding lawn is expansive, emphasizing the peaceful rural setting.
Home in Salem

Historic Farm Stay | Heated Pool + Hot Tub

PetsWalkabilityCondition

4.98 out of 5 average rating, 214 reviews
Guest favourite
The exterior shows a modern home embraced by lush greenery. A wooden deck with a railing wraps around the entrance, complemented by well-maintained landscaping featuring shrubs and plants. Trees provide a natural backdrop, enhancing the tranquil rural setting.
Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

Outdoor spacesPetsAmenities

4.93 out of 5 average rating, 109 reviews
Top Guest favourite
The backyard features a large heated pool with clear blue water surrounded by a concrete patio. Colorful lounge chairs are positioned around the pool, with a shaded area provided by umbrellas. Lush greenery and potted flowers add color to the tranquil setting.
Home in Corinth

Pool/Hot tub, king bed, between Lk George/Saratoga

PetsWalkabilityNearby

4.97 out of 5 average rating, 299 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

Outdoor spacesPetsHeating

4.92 out of 5 average rating, 223 reviews

Private, pet-friendly home rentals

Guest favourite
A log-sided cabin is surrounded by lush greenery under a clear blue sky. The structure features a distinctive half-moon window and a green metal roof. A spacious deck with outdoor seating and an umbrella is visible, inviting relaxation in a natural setting.
Cabin in Woodford

Lakeview Cabin in the Mountains - beautiful

WalkabilityOutdoor spacesFamily

4.9 out of 5 average rating, 161 reviews
Top Guest favourite
A bright and airy living room features large windows adorned with soft, flowing curtains, allowing natural light to fill the space. A teal sofa and a mustard yellow couch are arranged around a decorative coffee table, enhancing the welcoming atmosphere. Vintage decor and plants add character.
Apartment in Salem

Yellow Door Inn

Outdoor spacesPetsParking

4.98 out of 5 average rating, 127 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**

PetsOutdoor spacesCheckout

4.98 out of 5 average rating, 542 reviews
Top Guest favourite
The exterior of Hygge House is highlighted by sleek wooden siding and a modern design. Large windows reflect the surrounding greenery, while a stone pathway leads to the entrance. Sunlight filters through the trees, illuminating the inviting facade set on a spacious grassy area.
Chalet in Stratton

Luxe HotTub, Sauna, Fall Leaves, Stratton /Mt Snow

WalkabilityOutdoor spacesBarbecue

4.96 out of 5 average rating, 174 reviews
Top Guest favourite
The entryway features a welcoming entrance with a wooden door, adorned with a green wreath. A glimpse into the bright interior reveals modern seating and natural light streaming through large windows, enhancing the inviting space that awaits inside.
Chalet in Wilmington

Snug Chalet - Wi-Fi + Close to Mount Snow

PetsOutdoor spacesLayout

4.97 out of 5 average rating, 148 reviews
Guest favourite
Cabin in Woodford

400+ Airbnb Visits: Incredible Mountain Cabin

Outdoor spacesWalkabilityCheckout

4.85 out of 5 average rating, 391 reviews
Guest favourite
A welcoming living area features a comfortable sectional sofa adorned with soft cushions. A modern entertainment center with a large screen is positioned on the wall, complemented by an electric fireplace. A tasteful coffee table holds decorative items, enhancing the cozy ambiance.
Guesthouse in Petersburgh

The Little Hoosic House

PetsOutdoor spacesBathroom

4.8 out of 5 average rating, 103 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

Outdoor spacesWalkabilityBackyard

4.98 out of 5 average rating, 112 reviews

When is the best time to visit Bennington?

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Avg. price$246 AUD$251 AUD$239 AUD$251 AUD$276 AUD$246 AUD$262 AUD$275 AUD$260 AUD$283 AUD$241 AUD$244 AUD
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