
Family-friendly holiday rentals in Plymouth
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Top-rated family-friendly rentals in Plymouth
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Secluded tiny house resort - DOG FRIENDLY
New tiny house, never lived in, but made to be comfortable. All amenities included: Air-condition, heat, WiFi, TV with cable, shower, tub, dry toilet, small full loft bed and full size couch futon, fire pit, river for swimming or fishing right out the door, small refrigerator, microwave, hot plate, toaster.ear three ski resorts (Killington, Okemo, Pico), Appalachian Long Trail two miles away, swinging bridge on trail beginning, White Rock hiking, lakes near for paddle boarding. Hot tub shared.

~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.

Howling Wolf Farm Yurt--A Magical Glamping Retreat
Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

Vermont Home Central to Ski Areas-No Cleaning Fees
Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

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.

Cabin on the Hill
Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

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 250 acre property.

Cozy Little Spot (Self Check-in)
Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

Quiet Couples Retreat near Killington and Okemo
Clean and comfortable rural guest house in quiet and serene setting on 68 acres of land in Plymouth on Vermont Route 100, a top 10 scenic road in the US. Only 15 minutes from Killington and Okemo and minutes from hiking, lakes, fishing, boating, swimming, and a state beach and boat landing. Historic Woodstock is 15 miles away. Guests must be 21+. Inquiries from guests with no prior reviews on Airbnb will be further screened.

Love Shack Yurt on Star Lake (100% off grid)
Glamping at its finest. Bring everything but the bed. Enjoy sunsets and star gazing lakeside. No running water or electricity. Clean & custom built outhouse for a toilet. You will need to bring bedding, size king. Please note: self cleaning policy. Leave it in great condition for your fellow travelers. Woodstove for heat, provide your own wood. One King Bed with mattresses and top sheet ONLY. IG@YURTlilyPAD
Popular amenities for Plymouth family-friendly rentals
Family-friendly home rentals with a hot tub

Log Cabin: Amazing Views, River Frontage, Hot Tub

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Scandinavian design Chalet w/ private hiking trail

Renovated 1BR, Walk to Lifts, Covered parking

Special Retreat in Nature, Woodfired Tub

Canyons Unit: 1 mile to F&W Summer Camp w/ HOT TUB

Newly renovated ski retreat at Killington

Private Barn On a Hilltop in Fairlee, Vermont
Family- and pet-friendly home rentals

Rustic Cabin in foothills of Green Mountains

The Cozy Little Red Cabin

Private Hilltop farm apartment

The Cluck House

Private Cabin/PetsOK/Minutes to Okemo/AC/Fast Wifi

Snowcub- AC, Pool, Hot tub, Tennis, Grill!

Glamping Cabin with Private Pond and Mountain View

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

Renovated unit, prime location! Shuttle on/Ski off

Comfy ski in/out studio at base of Pico-Killington

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

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

One Bedroom Suite Near Okemo

Serene Top Floor Condo (resort style amenities)

#45 Luxury Ski & Summer Condo with Private Sauna

Hotel Chic - Home Comfort -Ski Easy.
Quick stats about holiday rentals that are family-friendly in Plymouth
Total rentals
130 properties
Nightly prices starting at
$139 AUD before taxes and fees
Total number of reviews
5K reviews
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Wi-Fi availability
130 properties include access to Wi-Fi
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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
- Magic Mountain Ski Resort
- Fort Ticonderoga
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Hooper Golf Course
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Brattleboro Ski Hill
- Fox Run Golf Club
- Ekwanok Country Club
- Bromley Mountain Ski Resort
- Montshire Museum of Science
- Whaleback Mountain
- Northeast Slopes Ski Tow
- Mount Sunapee Resort
- Baker Hill Golf Club