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Family-friendly vacation rentals in Windham

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Windham

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Cabin in Londonderry

4.82 out of 5 average rating, 446 reviews

Stunning Rustic Apple Barn - hot tub & sauna

VT’s #1 dream cabin with an overall 5 star rating since 2014 on airbnb! Brand new 4 person private hot tub, sauna & outdoor shower included! Clawfoot tubs inside & out! Originally a horse barn & tack room… We salvaged an old cattle barn for the remodel of this dream home!!! The rustic charm is 100% intentional and every original barn board and nail is back in place! This is upscale cabin living (Wolf and GE appliances) with an original VT antique vibe. Minutes to Magic, Bromley, Stratton, Okemo

Cabin in Londonderry

4.94 out of 5 average rating, 343 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Cabin in Jamaica

4.87 out of 5 average rating, 291 reviews

Green Mountain Modern House: iconic modern getaway

Our unique, contemporary home is in the heart of the Green Mountain National Forest, all while offering all the perks of modern luxury in a secluded setting. Our amenities include open concept living and dining room, sauna, wood burning fireplace, front deck, backyard with fire pit and Adirondack chairs, and contemporary design and decor throughout. Now with EV charger, mini-split AC and heat, on-demand backup generator and high speed Starlink wifi (200+ mbs)! Pets welcome with a $100 pet fee.

Home in Putney

4.94 out of 5 average rating, 370 reviews

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.

Cabin in Jamaica

4.89 out of 5 average rating, 370 reviews

Forest Cabin-Swim-Views-Fire Pit-7 min to Stratton

Authentic post & beam cabin surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Swimming hole at babbling brook on property, fire pit, hammock on porch, propane BBQ, picnic table, forest views. VCR & videos, turntable & records, games, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Staircase to loft, gas heat, wood stove, pellet stove. Full kitchen. Easy to use, odorless composting toilet. Dog friendly (sorry, no cats due to allergies).

Cottage in Chester

4.9 out of 5 average rating, 156 reviews

Green Mountain Country Cottage

Four bedroom cottage centrally located within less than 35 min. of 4 ski resorts, and next to the former Tater Hill golf club. Access to snowmobile trail on site, X-country skiing, hiking, fishing, shopping, restaurants, state parks nearby. In summer and fall mushroom foraging is very productive. For history buffs there is a revolutionary war era cemetery next to the property. Sleeps 10 to 12. The cottage is only available to family groups or responsible adults over 25. NO PARTYING ALLOWED.

Guesthouse in Springfield

4.86 out of 5 average rating, 352 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

Home in Winhall

4.98 out of 5 average rating, 368 reviews

Stunning mid-century house on 2.5 private acres

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.

Home in Grafton

4.97 out of 5 average rating, 146 reviews

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER

This beautiful circa 1850 farmhouse is nestled between two rivers. While it feels secluded, it is located right in Grafton Village and only a two minute walk from the Grafton Inn. There is an attached barn that has been converted to a great room with large fireplace and bar. We have a collection of bikes, tubes and snow shoes in the garage that guests are welcome to.

Rental unit in Andover

4.98 out of 5 average rating, 409 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Rental unit in West Townshend

4.91 out of 5 average rating, 327 reviews

Private Apt on Farm, Hot Tub with views!

Taft Hill Farm stay in a private 2-bedroom apartment plus sleeping loft, open-plan kitchen, living space; separate entrance; best views in Vermont! A great retreat for a family, a couple or a group of friends. Apartment is attached to main farmhouse on a historic 38-acre hillside farm. Extensive gardens & orchard, heritage breed cows, chickens and sheep.

Rental unit in Town of Rockingham

4.82 out of 5 average rating, 172 reviews

Apartment on Main Street

One bedroom apartment with kitchenette (mini-fridge, coffee maker, microwave, dishes etc.), full bathroom with laundry, and open living space. I am an English teacher, so there are lots of books! Apartment is located in the Village of Saxtons River- within easy walking distance from the Market, Vermont Academy, our new Park, and Main Street Arts.

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Popular amenities for Windham family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Plymouth

4.95 out of 5 average rating, 237 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Home in Colrain

4.93 out of 5 average rating, 167 reviews

Secluded Farmhouse Retreat - stunning views

Chalet in Ludlow

4.95 out of 5 average rating, 118 reviews

Okemo Ski Chalet with Hot Tub

Chalet in Killington

4.87 out of 5 average rating, 242 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

Home in Newfane

4.98 out of 5 average rating, 130 reviews

Peaceful cabin close to skiing & Brattleboro

Home in Ludlow

4.97 out of 5 average rating, 151 reviews

Ski Chalet with Hot Tub on Okemo Mountain

Loft in Ludlow

4.95 out of 5 average rating, 774 reviews

Spacious Renovated Barn Apt on 100 acres!

Home in Dover

4.98 out of 5 average rating, 132 reviews

Outdoor Paradise - Private Jacuzzi & Sauna

Family- and pet-friendly home rentals

Cabin in West Windsor

4.97 out of 5 average rating, 132 reviews

Cowshed Cabin Farm

Loft in Wilmington

4.93 out of 5 average rating, 187 reviews

Walk to Village/Lake Whitingham

Cabin in Cavendish

4.96 out of 5 average rating, 145 reviews

The Cozy Little Red Cabin

Home in Dummerston

4.99 out of 5 average rating, 338 reviews

Pinecone Pond

Rental unit in Ludlow

4.92 out of 5 average rating, 262 reviews

Okemo Vermont Getaway

Home in Danby

4.96 out of 5 average rating, 215 reviews

Comfortable farmhouse with stunning views

Home in Readsboro

4.86 out of 5 average rating, 124 reviews

December in Peaceful Vermont (Pet Friendly)

Rental unit in Montague

4.93 out of 5 average rating, 428 reviews

Beautifully renovated three bedroom

Family-friendly home rentals with a pool

Home in Salem

4.98 out of 5 average rating, 185 reviews

Magical Farm Getaway - a must visit!

Townhouse in Dover

4.96 out of 5 average rating, 143 reviews

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

Condo in Dover

4.87 out of 5 average rating, 228 reviews

Mt Snow Ski In/Out at Seasons

Condo in Killington

4.82 out of 5 average rating, 251 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

Condo in Killington

4.78 out of 5 average rating, 287 reviews

Serene Top Floor Condo (resort style amenities)

Condo in Killington

4.96 out of 5 average rating, 128 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

Condo in Hancock

4.85 out of 5 average rating, 142 reviews

Cozy Condo @ Jiminy Peak

Condo in Killington

4.93 out of 5 average rating, 415 reviews

PICO open Turkey week 1 bedroom 1 nite Ok shuttle

Quick stats about vacation rentals that are family-friendly in Windham

Total rentals
40 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
1.4K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

Destinations to explore