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

Boulder House - Extraordinary Luxury in the Woods!
From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

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

Spacious Loft with View
Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

Fat Cat Barn - Close Okemo & Magic, Vermont
Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

Mountain View Suite
Mountain View Suite offers tranquility and adventure with stunning views of Ragged Mountain. Just two miles from Ragged Mountain Ski Area, it features a master bedroom with a king-size bed, an open bunk room, a spacious living room with a 65-inch TV, gas fireplace, and a full kitchen. All standard amenities included. The suite’s large windows frame picturesque mountain scenery, bringing nature’s beauty indoors. Outdoors, sit and relax by the fire pit. Gym, Sauna & Cold Plunge Add-On available.

Vermont Botanical Studio Apartment
This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Village Flat with Antique Billiards
Charming and spacious first floor, 3 Bedroom, 1 Full Bath apartment. Sleeps 5 (1 King, 1 Queen and 1 twin). It is nestled in the center of the Bellows Falls village, a short 5-minute walk to downtown, where you will find great little shops and eateries. We are centrally located in Southern Vermont ~ 40 min from several ski areas (Okemo, Magic, Bromley, Stratton, etc.) about one hour from Killington Resort, Mount Snow, and Mount Sunapee (NH), and ~ 20 mins from Brattleboro, VT, or Keene, NH.

Monadnock Sunrise Forest Hideaway
Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for two adults (queen bed) and one kid (63" long fold down couch).

Treehouse Haven in Putney-All Seasons
Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting outhouse ☽ Tea & local coffee ☽ Hot outdoor shower-Closed Nov-April ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Retreat from the business of life; romance, with the family, or even a remote work sanctuary.

Private & Cozy Farmhouse in New Hampshire
Escape to our relaxing farmhouse in a quiet corner of Charlestown, NH. Overlooking farm fields, old barns and the Connecticut River, this property is the perfect quiet getaway! The house is within walking distance of the river as well as downtown Charlestown. It is located between Claremont, NH and Keene, NH making it a great midway point to access both for shopping, area attractions and a number of ski resorts. Minutes from I-91. Come and make yourself at home in this private getaway!

Minimal organic hideaway inspired by nature
Akasha, the first floor of this historic 1800’s carriage house in the center of Putney Village, was gutted and meticulously renovated by the hosts into a unique wellness apothecary and cafe and now serene and beautifully conceptualized open concept studio apartment. Aged wood tones, textured plaster walls, poured concrete counter tops and elegant dining bar imbue an old world tea house aesthetic with modern sensibilities. A unique space for quiet contemplation and relaxation.

Swiss Chalet Family Retreat!
Welcome to our family's Swiss style chalet! Inspired by trips to Davos, Switzerland, my grandparents built the chalet in the 1950s to be a family playhouse and gathering spot for their 6 children. It's kind of magical. Today, our large extended family still enjoys holiday celebrations here every year. Our kids love exploring the woodland trails and swimming in Center Pond. We hope you love it as much as we do! Note: the building also has two apartments on the first floor.
Popular amenities for Walpole family-friendly rentals
Family-friendly home rentals with a hot tub

~The ClubHaus~

Vermont Retreat Cabin | Romantic Nature Immersion

Private Apt. on Farm, Hot Tub with views!

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

The Owl’s Nest in Landgrove

Winter Dream! The Handle Lodge at Snowtree Condos

Beautiful Timber Frame Retreat

Vermont Farm Schoolhouse w/ Hot Tub, Sauna & Views
Family- and pet-friendly home rentals

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

Shakespeare’s Folly Side Farm and AirBnB.

The Oaks - secluded rural estate w/ amazing views

Triggers Cabin

Peaceful Beautiful Mountain Home Spectacular Views

Yurt In The Woods - Come to the Yurt.

Cozy Vermont Antique Sugar House with Fireplace

Large Private Lake House
Family-friendly home rentals with a pool

The 1770 House

The Brick House on Washington Street

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Beautiful rustic woods and fields retreat.

“Sugar Maple” Rustic 4x4 Cabin Getaway, Fireplace

Walk to Mt. Snow-Spa-Summer Pool

In-law Apartment, Full Kitchen, Near Mt Wachusetts

Hollywood Bungalow in the Berkshires #C0191633410
When is the best time to visit Walpole?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ808 | ﺩ.ﺇ826 | ﺩ.ﺇ808 | ﺩ.ﺇ881 | ﺩ.ﺇ727 | ﺩ.ﺇ892 | ﺩ.ﺇ881 | ﺩ.ﺇ881 | ﺩ.ﺇ889 | ﺩ.ﺇ925 | ﺩ.ﺇ889 | ﺩ.ﺇ944 |
| 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 vacation rentals that are family-friendly in Walpole

Total vacation rentals
Explore 20 vacation rentals in Walpole

Nightly prices starting at
Walpole vacation rentals start at ﺩ.ﺇ477 per night before taxes and fees

Verified guest reviews
Over 1,010 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Walpole vacation rentals include wi-fi access

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

4.9 Average rating
Walpole stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Okemo Mountain Resort
- Stratton Mountain
- Killington Resort
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Monadnock State Park
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Snhu Arena
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Montshire Museum of Science
- Dartmouth College
- Emerald Lake State Park
- Mount Sunapee Resort
- Mount Greylock
- University of Massachusetts Amherst
- Southern Vermont Arts Center
- Massachusetts Museum of Contemporary Art




