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

Glamping Cabin with Hot Tub on Flower Farm
<b>Vermont's Most Wish Listed</b> ﹏﹏﹏ Nestled in a wooded grove on Tanglebloom Flower Farm, this unforgettable glamping-inspired farm stay invites you to escape the everyday & immerse yourself in nature - comfortably. Designed with a clear roof looking up to the trees and screened sides to let in the breeze, the handmade tiny cabin invites you to slow down. Explore southern Vermont's hikes, farmer's markets & swimming holes or stay put. Perfect for a romantic couples retreat or solo getaway.

River View apartment
Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .

Cozy Vermont Antique Sugar House with Fireplace
Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

Custom cabin by the river in Newfane, VT
OPEN mid-MAY-OCTOBER. Our beautiful one-room custom cabin is on the edge of the woods surrounded by the Rock River. It's freshly appointed, with a king-size bed, is spotlessly clean and very romantic. The cabin has simple cooking facilities (details below) and an outdoor grill, twinkle lights on the deck, hammock, and 2 fire-pits, one by the cabin, and one on the beach. One COMPLIMENTARY BREAKFAST is included, with homemade popovers, fresh out of the oven. A smoke-free property.

~Serene Barn Retreat~
Peaceful, romantic retreat in this stunningly large, 1850's remodeled barn apartment. The historic barn is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

Peaceful cabin close to skiing & Brattleboro
Country privacy close to the best of Southern VT! This spacious home is close to skiing (20 min to Mt. Snow; 35 min to Stratton), river swimming holes, hiking, biking, art galleries and great restaurants. Open concept with fireplace, cook's kitchen, jet bathtub, gardens, winter hot tub off deck, and large patio and fire pit give the perfect vibes for your VT gathering. Secluded from neighbors but close to amenities, this home is a comfortable and peaceful retreat.

Contemporary forest eco-retreat, mountain views
This is an open, light-filled one-Bdm apartment on the lower level of our hillside home, surrounded by forests, with stunning views. Your space is 719 sf + access to laundry. We are fully vaccinated, and ask the same of guests. If you think you may have Covid please tell us. We welcome all kinds of people, regardless of race, ethnicity, gender, etc. We may ask questions before accepting people who don’t have many prior reviews. We don't take pets, sorry.

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.

Cozy Cabin in Southern VT
Take it easy at this tranquil getaway. Fall asleep to chirping bugs and wake up to birdcalls. This is a quiet, lovely cabin in Newfane VT. Read a book, walk the meditation circle, swing in the hammock, and explore all that Southern VT has to offer. Close to swimming holes, hikes, country stores, flea and farmers' markets, and ski mountains (Mt Snow and Stratton) Pets and children are welcome, but there is only one queen bed.

Modern Cabin with Outdoor Spa on Vermont Farm
Romantic modern cabin with private hot tub on a 100-acre Vermont farm. This Scandinavian-style retreat features soaring windows, a king bed with luxury linens, a cozy fireplace, and a sleek kitchen. Perfect for couples seeking a peaceful getaway, farm stay, or eco-friendly escape. Soak under the stars, meet our friendly goats, and enjoy the beauty of southern Vermont from your light-filled solar-powered cabin.

Cottage
The "Rustic" cottage is furnished with a queen bed, sofa and dining table. There is a small deck with patio furniture, fire ring with wood supplied, and a gas barbecue. It can accommodate 2 people comfortably. Private with parking. Host in separate house. Wi Fi from Xfinity, but please note that it can be patchy. Roku TV WI FI connected to router.

Cozy Train Depot in Putney Vermont
Charming and cozy 1 bedroom house in Putney, Vermont. A former train depot, this home is just a few minutes walk to the Connecticut River with boat launch for enjoying fishing, swimming, canoeing and kayaking. Or curl up in the window seat and enjoy the fire!
Popular amenities for Dummerston family-friendly rentals
Family-friendly home rentals with a hot tub

Mountain View 4x4 Rustic Cabin Retreat w/Fireplace

Private Brook Chalet: Hot Tub, Fire pit, Mt. Snow

Hot Tub & Game Room - Ski Mt. Snow/Stratton

Boulder House - Extraordinary Luxury in the Woods!

Schoolhouse Spa Retreat on a Vermont Farm

Modern Downtown 12ppl Hot Tub Fire Pit Games

Stunning Rustic Apple Barn - hot tub & sauna

A frame cabin with Hot tub near Stratton, VT
Family- and pet-friendly home rentals

Clark Farm-2 Master-Suites, Great kitchen, views!

Spacious Brattleboro home on river, walk to town

The Post Haus: one-of-a-kind modern VT experience

The Vermont Farmhouse|Hiking|Dog Trails|Village

Private Hilltop farm apartment

Snug Chalet - Wi-Fi + Close to Mount Snow

Log Cabin King Beds AC Near Hike Bike Swim Golf!

Home with a spring fed Koi pond and mountain view
Family-friendly home rentals with a pool

Winter Dream! The Handle Lodge at Snowtree Condos

Adams Farm-"The Little Farmhouse"

The Brick House on Washington Street

One Bedroom Suite Near Okemo

Walk to Mt. Snow-Spa-Summer Pool

Silver Brook Cabin

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Hollywood Bungalow in the Berkshires #C0191633410
Quick stats about holiday rentals that are family-friendly in Dummerston

Total holiday rentals
Explore 20 holiday rentals in Dummerston

Nightly prices starting at
Dummerston holiday rentals start at $141 AUD per night before taxes and fees

Verified guest reviews
Over 1,670 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Dummerston holiday rentals include Wi-Fi access

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

4.9 Average rating
Dummerston stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Pet-friendly rentals Dummerston
- Rentals with a patio Dummerston
- Rentals with a washing machine and dryer Dummerston
- Rentals with outdoor seating Dummerston
- Rentals with a fireplace Dummerston
- Rentals with a fire pit Dummerston
- Family-friendly rentals Windham County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Killington Resort
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Stratton Mountain Resort
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Emerald Lake State Park
- Mount Sunapee Resort
- Mount Holyoke College
- Mount Greylock
- Smith College
- Berkshire Museum
- Southern Vermont Arts Center
- Mount Monadnock
- Look Memorial Park




