
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.

Peaceful Mill with Waterfall - Home Away From Home
Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated remote workspace

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

~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

Canyons Unit: Skyeship Gondola 2 miles w/HOT TUB
The Canyons Unit is a recently updated, fully separate, ground level, 2 bedroom/ 1 bathroom apartment in our four-family French Chalet. Located 1 mile to lakes and summer camps and 2 miles from Killington’s Skyeship Gondola. 15 minutes to Killington’s main base area and 20 minutes to Okemo. If you would like to book multiple units, check out our other listings by clicking my Host Profile Picture below. The units at this location are called "the Moguls Unit", "The Ledges", and "The Glades".

Waterfront Vermont Lake House w/ Panoramic Sauna
We invite you to come stay and experience all of the beauty that Vermont has to offer at Lake St. Catherine. Located on the west side of the lake off a quiet private drive with almost 100ft of lake frontage, there are few spots with a better view. Watch the sun rise each morning from either our private decks. Explore the lake by canoe or kayak; both available for our guests. If the dates you're looking for are booked, message us for availability at our second location! Follow us @vtlakehouse

Weasley's Enchanted Treehouse @ Vermont ReTREEt
Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

Treehouse compound, no cleaning fee
The rental includes both treehouses (toilet in each), cooking/eating pavilion (only cold water at sink) (outhouse nearby), outside shower (cold), firepit. Additional guests above the 2 included in per night stay are $30 per person per night up to a maximum of 11 guests during the warmer months and 5 guests total during the cooler ends of the season (June and mid Sept to mid Oct). Beds: 3 doubles, 5 singles. No pets allowed. Not ideal for very young children or people with mobility issues.

THE LOFT, stunning views from a timber framed barn
Welcome to "The Loft". A lofted space 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. For more go to @theloft.vt

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.

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub
Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

Kingsley Grist Mill Waterfall & Private Beach OMG
One of the "World's Most Amazing Vacation Rentals " as seen on the exciting NetFlix series, s.2, ep.7 and on HGTV's "You Live in What?, s.2, ep.1. Join us this season for the romance, the history, the breakfast, the natural mineral spring tap water, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. No cleaning fees added. Come make history with us ! Near Killington & Okemo Mtns.

Log Cabin: Amazing Views, River Frontage, Hot Tub
A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.
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

The Owl’s Nest in Landgrove

Romantic Treehouse- PVT Hot tub, 20 Min to KLT

Relaxing Countryside Oasis!

Kolelemook Cottage!

Newly Renovated, Hot tub, 2min to Killington lift

Glamping Cabin with Hot Tub on Flower Farm

Secluded tiny house resort - DOG FRIENDLY
Family- and pet-friendly home rentals

Hideaway Cabin by the Stream on 27 Acres

Log Cabin, King Beds & 7 Min from Stratton Mtn

Beautiful Woodstock Home-Perfect for entertaining

Apple Blossom Cottage: A Tiny House

Yurt In The Woods - Come to the Yurt.

Garden Retreat, Lake Fairlee, Dartmouth & Ski-way

The Guest House at Sky Hollow

Private Modern Cabin w/View of Fields, Hills
Family-friendly home rentals with a pool

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

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

Trail Creek - ski home!

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

Moon Valley Country Retreat no clean fee pets yes

Lower Yurt Stay on VT Homestead

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

Newly renovated ski retreat at Killington
When is the best time to visit Plymouth?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £300 | £337 | £275 | £206 | £228 | £220 | £238 | £220 | £212 | £246 | £224 | £334 |
| Avg. temp | -7°C | -6°C | 0°C | 7°C | 14°C | 18°C | 21°C | 20°C | 15°C | 9°C | 3°C | -3°C |
Quick stats about holiday rentals that are family-friendly in Plymouth

Total holiday rentals
Explore 140 holiday rentals in Plymouth

Nightly prices starting at
Plymouth holiday rentals start at £114 per night before taxes and fees

Verified guest reviews
Over 5,470 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
140 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
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Killington Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Dartmouth College
- Montshire Museum of Science
- Emerald Lake State Park
- Mount Sunapee Resort
- Middlebury College
- Southern Vermont Arts Center
- Warren Falls
- Trout Lake
- Camp Plymouth State Park
- Lowell Lake State Park




