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

Mountain side acres
10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Lawrence Cottage
Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

New Cabin in Jamaica
Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

The Chick Inn
This is a two-story, renovated barn adjacent to the chicken coop in rural Vermont with views of the forests. It has brand new floors, a new kitchenette, and fresh look. (Some renovation is still taking place.) The chicken coop is just next door but the birds are free-range and range they will. Enjoy a private, hot shower in the garden, just outside. This listing is only suitable for people comfortable with dogs, cats, and chickens which will undoubtedly greet you outside during your stay.

Apple Blossom Cottage: A Tiny House
The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Cabin w/Hot tub, Sauna near Mt.Snow & Stratton.
Rustic cabin situated on a quiet cul-de-sac between Mt. Snow & Stratton Mtns. Features 2 beautiful wood burning fireplaces, sauna, outdoor hot tub & fire pit and Generac stand by generator. Modern kitchen on main floor w/4 bedrooms and 2 full bathrooms . Huge open concept layout perfect for entertaining. Natural light beams in onto the loft and master bedroom just upstairs from the main floor. Basement offers a pull out couch w/ easy access from driveway. Coffee /Firewood included.

Rustic Cabin in foothills of Green Mountains
Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials, water, coffee, tea, milk, fresh eggs + homemade soap. It has an indoor compost toilet, outhouse + outdoor shower (May-Oct) Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

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.

Okemo Ski-in/Ski-out, Steps to lift Condo
Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

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.

Cozy Camp in Vermont
This cozy camp located in beautiful East Dover, is on a secluded road off the beaten path where the babbling brook can be heard. Close to Mount Snow, Lake Whitingham, Lake Raponda, and only 25 minutes to Brattleboro the adventures are endless! Visit the serenity and beauty of Southern Vermont- especially in Fall during “leaf peeping”. This is a camp-style cottage with rustic charm. Snow tires are a MUST- Nov. - Apr.

Winter Dream! The Handle Lodge at Snowtree Condos
The Handle Lodge at Snowtree Condos is a modern 1BR condo at the base area of Mount Snow. Comfortably sleeps 6 adults and is fully equipped with everything you'll need for a fun getaway with friends and family. Make a meal in the beautiful kitchen or step out on the balcony for stunning mountain views. Our modern and cozy decor, the lovely views, and proximity to the mountain make it a great place to relax and recharge.
Popular amenities for Wardsboro family-friendly rentals
Family-friendly home rentals with a hot tub

Private Apt. on Farm, Hot Tub with views!

Vermont Retreat Cabin, Romantic Winter Wonderland

Mt Snow Ski In/Out at Seasons

Beautiful Timber Frame Retreat

Leonard’s Log - Private Hot Tub, Fire Pit, A/C

Luxe Hot Tub, Sauna 8-12 min Stratton & Mount Snow

MountSnow 8 Min, HotTub, GameRoom, FirePit, DogsOk

Mod Cabin in woods Hot Tub near Stratton & MtSnow
Family- and pet-friendly home rentals

#32 Top Floor-Newly Renovated! Room 32-Horizon Inn

Snug Chalet - Wi-Fi + Close to Mount Snow

Log Cabin, King Beds & AC Near Hike/Swim/Golf/Bike

Newfane, studio on 33 acres of Vermont beauty

Great 2 bedroom condo at Stratton Mountain

Cozy Vermont Antique Sugar House with Fireplace

Cozy summer cottage in the woods of S. Vermont

“Sugar Maple” Rustic 4x4 Cabin Getaway, Fireplace
Family-friendly home rentals with a pool

Stratton/Mt Snow minutes away! Hot tub + Game room

Stratton Long Trail House: Quick Walk to Lifts!

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

Mount Snow Ski Chalet

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)

Mt Snow 2 Bdrm Condo - Free Ski Shuttle

Cozy Bear- 1 mile to Mt Snow Ski Home

Ski in-out Seasons Condo on mtn-sports center-pool
When is the best time to visit Wardsboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £274 | £294 | £239 | £186 | £191 | £173 | £196 | £188 | £193 | £191 | £206 | £267 |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about holiday rentals that are family-friendly in Wardsboro

Total holiday rentals
Explore 90 holiday rentals in Wardsboro

Nightly prices starting at
Wardsboro holiday rentals start at £89 per night before taxes and fees

Verified guest reviews
Over 4,770 verified reviews to help you choose

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
90 of Wardsboro holiday rentals include wifi access

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

4.8 Average rating
Wardsboro stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
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- Pet-friendly rentals Wardsboro
- Rentals with a washing machine and dryer Wardsboro
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- Rentals with outdoor seating Wardsboro
- Rentals with a hot tub Wardsboro
- Rentals with pools Wardsboro
- Rentals with a firepit Wardsboro
- Rentals with a fireplace Wardsboro
- Cabin rentals Wardsboro
- Rentals with a patio Wardsboro
- Family-friendly rentals Windham County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Killington Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Fox Run Golf Club
- National Museum of Racing and Hall of Fame
- Mount Sunapee Resort
- University of Massachusetts Amherst
- Crooked Lake
- Mount Monadnock
- Rensselaer Polytechnic Institute
- Massachusetts Museum of Contemporary Art
- Southern Vermont Arts Center




