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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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Home in Ludlow

4.87 out of 5 average rating, 137 reviews

1st floor, Okemo contemporary country 3 BR 2 BA

Family-friendly, pet-friendly, clean, comfortable, contemporary country ski cabin on Okema shuttle buss route in Ludlow, VT, a few minutes from mountain. Very easy access to outdoor activities: skiing, hiking, lakes, boating, hunting, snowmobiling, fly-fishing. Updated, comfortable, light filled ambiance. Great location, 10 minute walk to downtown (2 minute drive). Great for groups, couples, families. Recently renovated. New butcher block counter-tops and island, all new kitchen, new bathrooms.

Guest favourite

Cottage in Chester

4.91 out of 5 average rating, 160 reviews

Green Mountain Country Cottage

Four bedroom cottage centrally located within less than 35 min. of 4 ski resorts, and next to the former Tater Hill golf club. Access to snowmobile trail on site, X-country skiing, hiking, fishing, shopping, restaurants, state parks nearby. In summer and fall mushroom foraging is very productive. For history buffs there is a revolutionary war era cemetery next to the property. Sleeps 10 to 12. The cottage is only available to family groups or responsible adults over 25. NO PARTYING ALLOWED.

Guest favourite

Home in Weston

4.86 out of 5 average rating, 109 reviews

4 Bedroom Family Ski House w/ WiFi, cable!

This family heirloom sits tucked away in the trees just off of Chester Mountain Road. Short trips to Bromley, Okemo, Stratton and Magic Mountains. Sleeps 8 comfortably with room for up to 10 on pull out couches. You will fall in love with the retro feel of this house, it's straight out of the 1980's, and has kept that charm over the years. We have consistently updated it with all of the amenities needed to relax, including Air Conditioning, High Speed wifi, Cable, big screen TV and sound bar.

Guest favourite

Apartment in Wilmington

4.91 out of 5 average rating, 129 reviews

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

Home in Jamaica

4.86 out of 5 average rating, 285 reviews

Yellow Sweetie at the Base of Stratton

Our adorable home, The Yellow Sweetie, is located in a convenient setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

Guest favourite

Home in Salem

4.98 out of 5 average rating, 188 reviews

Magical Farm Getaway - a must visit!

Beautifully restored 18th century farmhouse situated on 4.6 private acres within a 180 acre working farm. Five bedrooms, wood stoves, ample living space, and a cheery sun room with gorgeous views make this house one of a kind. Our backyard features an in-ground, heated, salt water swimming pool (open May to mid-Oct), fire pit (open year-round), large outdoor dining table, gas grill, and a deck with lounge seating and jacuzzi (open year-round). Parties and events are not allowed.

Guest favourite

Home in Whitehall

4.93 out of 5 average rating, 138 reviews

Lakefront A-Frame Home Emerald Lake, NY

A Frame style home with 100 + feet of lake frontage. 2 bedroom plus a loft bedroom with 2 twin beds. 1 and 1/2 baths and large open basement A-frame style home on a small, quiet lake in upstate NY in the town of Hampton/Whitehall, NY (not on Lake George), 5 miles from the VT border, 33 miles from Lake George village, with a screened in porch, a large deck, and a grill provided. Water activities 2 kayaks 1 - 4 person paddle boat

Guest favourite

Apartment in Chester

4.89 out of 5 average rating, 495 reviews

Beautiful 2 Bedrooms in Mountains w/ full kitchen

Ready for a Vermont getaway? In heart of ski area w/ A+restaurants & charming villages are two cozy bedrooms on 2nd fl of larger apt complex. Each bedroom has separate toilet/sink room, shared shower room for your and your guests alone. Hallway living room at one end with 2 couches, desk and TV Other end is full compact kitchen with dishwasher, stove and over, full size refrigerator, coffee maker and microwave.

Guest favourite

Home in Ludlow

4.97 out of 5 average rating, 154 reviews

Ski Chalet with Hot Tub on Okemo Mountain

Much of the house newly renovated in the Fall, 2023. Relax in this 3-level (1700+ sq. ft) ski chalet that's a 4 min drive to the Okemo Mountain Resort and the center of town, and a 6 min drive to Jackson Gore. Take in the 180-degree views of your wooded backyard with floor-to-ceiling windows and unwind in front of the fireplace or relax in the Jacuzzi hot tub in your private oasis on the mountain.

Guest favourite

Apartment in Ludlow

4.92 out of 5 average rating, 147 reviews

Great Downtown, walk to everything

Get the best of both worlds with this completely renovated Village apartment. Surrounded by the best restaurants and shopping . . . On Okemo's free winter shuttle route for hassle-free skiing. Welcoming and comfortable space with gas fireplace, full kitchen, master bedroom, private entrance. One queen, one full futon in the living room provide additional sleeping for guests.

Guest favourite

Apartment in Londonderry

4.96 out of 5 average rating, 574 reviews

Vermont Getaway Apartment

A 2 bedroom apartment attached to our home, close to Stratton, Bromley, Magic, Okemo & Mt Snow Skiing, hiking, fishing, golfing, tennis, outlet shopping and fine dining all close by. Manchester a short drive. Hot tub available from 8am-8pm. Level 2 EV charger available for a $10 cash fee (and give us advance notice if possible so we can open the garage for you).

Guest favourite

Home in Dover

4.88 out of 5 average rating, 240 reviews

Mt Snow retreat, ski & summer

Warm and welcoming space for relaxation and play, your home base for VT recreation. 7 min. drive to Mount Snow, convenient location. Easy access to hiking, mountain biking, x-c skiing, golf course, and more! Sleeps 5 easily. ~10 min. walk to Moover, 7-11, restaurants. INTERNET - There is a fiber optic connection and the plan speed is 50Mbps down / 30Mbps up.

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Popular amenities for Dorset family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Home in Plymouth

4.95 out of 5 average rating, 243 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Guest favourite

Farm stay in Valley Falls

4.89 out of 5 average rating, 223 reviews

Country Getaway Lodge / Ranch

Guest favourite

Chalet in Ludlow

4.95 out of 5 average rating, 120 reviews

Okemo Ski Chalet with Hot Tub

Guest favourite

Home in Cavendish

4.84 out of 5 average rating, 144 reviews

Okemo-Ludlow, fireplace, hottub, sleeps 13

Farm stay in Londonderry

4.82 out of 5 average rating, 136 reviews

Cozy Award Winning Farmhouse - hot tub and sauna!

Guest favourite

Home in Newfane

4.98 out of 5 average rating, 133 reviews

Peaceful cabin close to skiing & Brattleboro

Home in Argyle

4.83 out of 5 average rating, 150 reviews

Expansive Lakehouse with Jacuzzi

Apartment in West Townshend

4.9 out of 5 average rating, 335 reviews

Private Apt on Farm, Hot Tub with views!

Family- and pet-friendly home rentals

Guest favourite

Cabin in Jamaica

4.88 out of 5 average rating, 108 reviews

Cozy Log Cabin near Stratton/Mt. Snow-pet friendly

Guest favourite

Loft in Wilmington

4.92 out of 5 average rating, 191 reviews

Walk to Village/Lake Whitingham

Guest favourite

Cabin in Brattleboro

4.88 out of 5 average rating, 485 reviews

Cottage

Guest favourite

Apartment in Wilmington

4.93 out of 5 average rating, 181 reviews

Quaint cozy vermont apartment

Apartment in Town of Rockingham

4.82 out of 5 average rating, 174 reviews

Apartment on Main Street

Guest favourite

Chalet in Dover

4.92 out of 5 average rating, 294 reviews

A charming VT chalet

Guest favourite

Tiny homes in Jamaica

4.94 out of 5 average rating, 1,233 reviews

Apple Blossom Cottage: A Tiny House

Guest favourite

Apartment in Newfane

4.97 out of 5 average rating, 442 reviews

Rock River Retreat: VT Oasis Pet Friendly

Family-friendly home rentals with a pool

Guest favourite

Townhouse in Dover

4.96 out of 5 average rating, 145 reviews

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

Guest favourite

Chalet in Wilmington

4.95 out of 5 average rating, 93 reviews

Rustic Sunny Vermont Home near Mount Snow

Guest favourite

Condo in Dover

4.87 out of 5 average rating, 234 reviews

Mt Snow Ski In/Out at Seasons

Guest favourite

Guesthouse in Granville

4.9 out of 5 average rating, 869 reviews

Moon Valley Country Retreat no clean fee pets yes

Guest favourite

Home in Dover

5 out of 5 average rating, 57 reviews

The Villa - Industrial Farmhouse with Hot Tub

Home in Manchester

4.85 out of 5 average rating, 34 reviews

Your VT Ski House: Fireplace, Indoor Pool, Dogs

Home in Killington

4.87 out of 5 average rating, 31 reviews

Scenic 5 Bedroom Killington Mountain Vacation Home

Guest favourite

Home in Ludlow

4.78 out of 5 average rating, 46 reviews

Beautiful Okemo Farmhouse 0.7 mile from base lodge

Quick stats about vacation rentals that are family-friendly in Dorset

Total rentals
70 properties
Nightly prices starting at
$130 CAD before taxes and fees
Total number of reviews
2K reviews
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wifi availability
70 properties include access to wifi

Destinations to explore