
Family-friendly vacation rentals in Bennington
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Bennington
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Peaceful Get Away at Birds of a Feather Farm
Our cozy upstairs studio can accommodates up to 4 and is separate from the main house. Plush towels, linen, pillows and blankets. Kitchenette is fully stocked with everything you need for cooking. The private entrance is equipped with punch key lock to facilitate easy self check-in. A queen size sleep number bed, queen size pullout couch, table with four chairs, a dresser, one bathroom with shower, smart TV and WIFI. Heat and cooling. Spa services are available. For Booking & Fees contact host.

Birch House - lake, green trees + modern comforts
We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned space w/ cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. IG birchhousevt Please note that due to a severe allergy, it is difficult to accommodate animals

Escape the City- Vermont Studio
Our studio apartment is located minutes from Bennington College, and sits on 7 acres of land in the Grn. Mtn. National Forest. It's on the second floor of our home (above the garage) through a private entrance with a personal deck and outdoor seating. Take an afternoon stroll to the Mile Around Woods, or day hike to the white rocks! Walk the Ninja trail from the college to see the historic covered bridges, or drive 20-30 miles N to enjoy Vermont's best skiing, and shopping at designer outlets!

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.

Just Be Cabin
Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Monadnock Sunrise Forest Hideaway
Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for two adults (queen bed) and one kid (63" long fold down couch).

The Beer Diviner Brewery Apartment
The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

1 bedroom guest house on dead-end rd
Enjoy a peaceful and private space with 1 bedroom, 1 bath, full kitchen and on site parking. Last house on a dead end rd. 5 min from Southwestern VT Medical Center. 40 min from Mount Snow. 25 min from MassMoca. 15 min walk to Main St where you can enjoy great food and shops. No smoking on premises. Please note there is stairs separating the bedroom (downstairs) and living area, bathroom, and kitchen (upstairs). The stairs are steep and may be difficult for some people.

Cooper's Place
Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

Architectural GuestSuite
The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub
This historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

Airbnb @ Sweet & Savory Farmette
Welcome to the AirBnB situated on a small working farm. You are welcome to tour the grounds to say hello to all the animals. This place is for the birds! No really you will enjoy watching chickens, ducks, emus, geese, guinea fowl, and peafowl. The farm is also home to a herd of beautiful alpaca and resident llama, curious goats, and barn cats. There are working livestock guardian dogs who watch over the herd who will greet you from behind the fence.
Popular amenities for Bennington family-friendly rentals
Family-friendly home rentals with a hot tub

Log Cabin: Amazing Views, River Frontage, Hot Tub

Beautiful Timber Frame Retreat

Winter Dream! The Handle Lodge at Snowtree Condos

Cottage with a View

Vermont Retreat Luxe Yurt, Romantic & in Nature

HOT TUB & New Stylish Saratoga County Efficiency

Mountain side acres

Glamping Cabin with Hot Tub on Flower Farm
Family- and pet-friendly home rentals

Walk to Village/Lake Whitingham

Guest House at Hummingbird Hill

Quaint One-Story Vermont House with Mountain View

Glamping Cabin with Private Pond and Mountain View

Apple Blossom Cottage: A Tiny House

Yellow Door Inn

Love Shack Yurt on Star Lake (100% off grid)

5BR Rustic Mountain Sanctuary Dome Home
Family-friendly home rentals with a pool

Bear's Den - Mt Snow Townhome w/ Ski Home Trail!

Mt Snow Ski In/Out at Seasons

Moon Valley Country Retreat no clean fee pets yes

Newfane, studio on 33 acres of Vermont beauty

Cozy Cottage near lake

Near Saratoga – King Bed, Tub, Fire Pit & Movies

Cozy Vermont Antique Sugar House with Fireplace

Silver Brook Cabin
When is the best time to visit Bennington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$29,064 GYD | G$34,291 GYD | G$34,082 GYD | G$29,064 GYD | G$29,064 GYD | G$29,064 GYD | G$34,500 GYD | G$34,500 GYD | G$34,500 GYD | G$36,173 GYD | G$29,482 GYD | G$29,064 GYD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about vacation rentals that are family-friendly in Bennington

Total vacation rentals
Explore 20 vacation rentals in Bennington

Nightly prices starting at
Bennington vacation rentals start at G$23,000 GYD per night before taxes and fees

Verified guest reviews
Over 880 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Bennington vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Bennington rentals

4.9 Average rating
Bennington stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- West Mountain Ski Resort
- Saratoga Spa State Park
- Norman Rockwell Museum
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Beartown State Forest
- Hildene, The Lincoln Family Home
- Berkshire Botanical Garden
- Butternut Ski Area and Tubing Center
- Hooper Golf Course
- Lake George Expedition Park
- Albany Center Gallery
- Peebles Island State Park




