Family-friendly vacation rentals in Dorset

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Dorset

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

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Guest favorite

Cabin in Londonderry

4.94 out of 5 average rating, 343 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Guest favorite

Farm stay in Moreau

4.96 out of 5 average rating, 689 reviews

Cottage On The Farm

Our Hobby Farm Cottage is perfect for the low-maintenance solo adventurer, couples, or small family looking to get away. We offer a small farm feel and are centrally located between Saratoga Springs and Lake George. Be sure to check out our other listing, ‘Cabin On The Farm’ if traveling with friends and family but wish to stay in separate accommodations. Please refer to our Policies & Rules for information about the required waivers you'll receive after booking. *Please Read Entire Listing*

Guest favorite

Rental unit in Dorset

4.99 out of 5 average rating, 185 reviews

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 5 friendly horses, entertaining chickens, mountain views and a host who cares about you. The farm is a quiet, private, peaceful place with 30 acres to roam, but still close to Dorset and Manchester. Fields, mountains and a pond are all here. Good for couples and solo travelers who want an amazingly beautiful setting. This listing is more than a rental... it's an entire farm. Powered by solar to help the planet!

Guest favorite

Guesthouse in Granville

4.9 out of 5 average rating, 852 reviews

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Guest favorite

Home in Manchester

4.87 out of 5 average rating, 261 reviews

Manchester Center with Mt. Equinox View / In Town

The house is walkable to most of Manchester with an amazing view of Mt.Equinox from the front porch. The house is very spacious (1866 sqft) and is perfect for families or groups looking to avoid a cramped hotel room. The House is Dog friendly. Additionally, the house is a short 10 minute walk to the center of town which includes restaurants, coffee shops, and shopping. 7 MIN TO HORSESHOW. 10 min Bromley. 22 min Stratton. 25 min magic. 10 min emerald lake. There is no uber in town.

Guest favorite

Home in Mount Tabor

4.98 out of 5 average rating, 242 reviews

Cow Barn Lodge

Our home is located in MT. Tabor, Vermont, just off of Route 7, in a country setting with beautiful Mountain views of the Green Mountain National Forest, Dorset and Danby Mountains. The house is an old barn converted into a beautiful spacious home, on 4 acres. Snowmobiling from our place, plus 4 major ski areas less than 30 miles away. Hiking, fishing, swimming, golfing, and the Equestrian horse show are all nearby. as well as shopping in nearby Manchester and Rutland Vermont.

Guest favorite

Cottage in Shaftsbury

4.98 out of 5 average rating, 641 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated 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 350 acre property.

Guest favorite

Home in Dorset

4.98 out of 5 average rating, 120 reviews

The Nest at Birch Quarry

Our home is located mid-way between Dorset and Manchester VT. This mid 70's style home has been remodeled and updated. The rooms are tastefully decorated. New baths, a well appointed kitchen, large dining area, vaulted ceilings, large deck & marble patio w/ fire pit. Private setting surrounded by woods and quarry pond. The access is flat and off a paved road. 3 min to Dorset. 5 min to Manchester. 10 min to VT Horse Show. 15 min to Bromley. 25 min to Stratton.

Guest favorite

Home in Winhall

4.98 out of 5 average rating, 368 reviews

Stunning mid-century house on 2.5 private acres

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.

Guest favorite

Rental unit in Bennington

4.93 out of 5 average rating, 620 reviews

The Octopus's Garden

Welcome to the Octopus' Garden, a warm and cozy oasis located in the heart of Bennington, VT. This relaxing one bedroom suite, infused with amenities and much love, comfortably accommodates 2 people. This peaceful space is only a 10 minute walk to art, shops and dining and is the perfect hub for a variety of activities in Southern Vermont and Western Massachusetts.

Guest favorite

Rental unit in Andover

4.98 out of 5 average rating, 409 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!