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

~The ClubHaus~
Appreciate life at our peaceful home away from home in the Vermont Woods... Located a short drive from Killington and Okemo ski mountains, The ClubHaus is the perfect spot to unwind after enjoying four season New England activities. Breweries and great food are nearby in Woodstock, Manchester, and Dorset. Huge fireplace, hot tub, comfortable beds, and lots of thoughtful touches provided to welcome you to the ClubHaus family. Wifi, Netflix, and Disney+ included, no cable. @clubhausvt on IG

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.

Apartment in Vermont Historic Home
This lovely renovated 3-room apartment is attached to our 1885 Vermont italianate home, located is historic Middletown Springs, Vermont. We have been working on restoring this house, listed on Vermont's registry of historic homes, for a dozen years now. The apartment has its own entrance, full kitchen, and one spacious bedroom. The third room is a large sitting room with a shower and closet bath. Enjoy your morning coffee on the front porch, meet our chickens, and explore our garden.

Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Ogden's Mill Farm
Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

THE LOFT, stunning views from a timber framed barn
Welcome to "The Loft". The loft is a newly built apartment on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony.

Peaceful Ludlow Base 5 minutes to Okemo
Newly renovated, clean 1 BR apt. in historic house 2 blocks to town, 5 minute drive to Okemo, Buttermilk Falls, and 2 minute walk to the Ludlow Farmers Market. Enjoy complimentary coffee and local maple syrup while overlooking the town of Ludlow. Make yourself at home with a full kitchen/bath, wall-mounted flat screen TV, king bed, and comfortable futon. Free EV charging available. Kayaking, hiking, and golfing close by. We are dedicated to ensuring a top-notch experience!

River House Apartment - Dog friendly
Entire downstairs of a house with one double bed. There is nice bathroom with shower. There is a microwave, coffee, massage chair, outdoor grill and picnic table. Internet and cable provided with fire stick for the TV. Fire pit and hot tub are shared by other guests. Up to three and all size dogs or pets are allowed and welcome. The three acres has a lovely place for them to run and has been sprayed for ticks and mosquitos. Please note: key replacement $30 if lost or taken

Your home away from home
Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, skiing, golf, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

Beautiful 1 bedroom apartment with balcony
Bienvenue chez nous! Experience comfort and modern beauty in this completely renovated apartment attached to a historic Victorian home. The one bedroom apartment has a private bathroom and your own balcony to enjoy. Close to popular skiing areas of Mt Sunapee (20 minutes) and Okemo (35 minutes), in addition to enjoying local hiking and cycling at Mt Ascutney, Moody Park, and Arrowhead.

Serene Bus Getaway Among Rolling Farm Land
Tucked off a quiet dirt road, this stationary bus promises to provide you and yours an unforgettable accommodation for your next Upstate NY retreat. Come stay in the Sleepy Tire, and wake up to beautiful views of Vermont’s Green Mountains, an indoor bathroom with flushing toilet and hot shower, and WiFi so you can stay connected to those that matter.

Elegant Alpine Condo
Newly renovated 1-bedroom Whiffletree condo with upscale alpine style, minutes from l bike park, adventure center, and golf course. Fully stocked with essentials and includes a locker for your gear. Sleeps up to 4 with a king bed and queen pullout sofa. Cozy gas fireplace to complete your perfect fall getaway! Killington Reg #007718
Popular amenities for Plymouth family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy Bow House Perched in Trees w/ Hot Tub & View

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Log Cabin: Amazing Views, River Frontage, Hot Tub

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

Lower Yurt Stay on VT Homestead

SnowCub Pets Indoor Pool Hot Tub Sauna, FirePlace

Special Retreat in Nature, Woodfired Tub

Vermont Getaway Apartment
Family- and pet-friendly home rentals

Picturesque Cabin on the Mettowee

Cowshed Cabin Farm

Apartment on Main Street

Runamuk Farm

Yurt In The Woods - Private Refuge

Cozy Home in Poultney, Vermont.

My house is your house!

Camping on a Private Pond
Family-friendly home rentals with a pool

Luxury Condo Tucked in the Heart of Killington

"Mountain View" Rustic Cabin Retreat w/Fireplace

Epic Views of the Green Mountains

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

Winterplace - Steps away from Slopes

Beautiful rustic woods and fields retreat.

SKI ON/OFF Spruce Glen B | AC | Sauna| Fireplace

Cozy Vermont Antique Sugar House with Fireplace
Quick stats about holiday rentals that are family-friendly in Plymouth

Total holiday rentals
Explore 130 holiday rentals in Plymouth

Nightly prices starting at
Plymouth holiday rentals start at £68 per night before taxes and fees

Verified guest reviews
Over 5,280 verified reviews to help you choose

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
130 of Plymouth holiday rentals include wifi access

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

4.8 Average rating
Plymouth stays are highly rated by guests – averaging 4.8 out of 5!
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- Family-friendly rentals Windsor County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Hooper Golf Course
- Bromley Mountain Ski Resort
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Brattleboro Ski Hill
- Ekwanok Country Club
- Fox Run Golf Club
- Whaleback Mountain
- Montshire Museum of Science
- Baker Hill Golf Club
- Mount Sunapee Resort