Family-friendly vacation rentals in Windham County

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Top-rated family-friendly rentals in Windham County

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

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Guest favorite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. 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!

Nov 5 – 12

G$21,384 GYD per night

Guest favorite

Apartment in Wilmington

4.88 out of 5 average rating, 279 reviews

Globetrotter Retreat - Minutes to the Mountain

Newly renovated, fully furnished apt in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt sleeps 4 people in comfort. Private balcony overlooks rolling river. Steps from many restaurants, bars & shopping. Supermarket is a short walk. FreeMoover bus stop across the street - leave your car parked & ride for free to local destinations! No guest under 18 years old.

Oct 11 – 18

G$23,670 GYD per night

Guest favorite

Home in Putney

4.94 out of 5 average rating, 338 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.

Apr 12 – 19

G$23,091 GYD per night

Guest favorite

Guesthouse in Brattleboro

4.99 out of 5 average rating, 199 reviews

Light Filled Loft in the Vermont Countryside

Our spacious, tranquil, light-filled Barn Loft is thoughtfully and creatively designed. Complete with a living area, sleeping alcove, flat-screen TV, full kitchen, dining area, and large bathroom with a deluxe shower. A private deck with seating that looks out into our lovely Vermont woods and verdant gardens is attached to the loft. Stay a night or a week, there is plenty to do in every season. We are a friendly, welcoming, worldly, family. We look forward to hosting you at our country home.

Jul 17 – 24

G$27,429 GYD per night

Guest favorite

Chalet in Dover

4.93 out of 5 average rating, 265 reviews

A charming VT chalet

Charming chalet nestled in the Mt Snow valley. Relax to the sound of a babbling brook in the back yard while you hang around a stone fire pit! Unwind in the quiet serenity of this country home complete with fully equipped kitchen with a newly installed gas fireplace , a comfy open living room with flat screen cable tv & DVD player Roko & High speed Internet . We have a lock box located on the post near the front entrance. combo provided upon arrival . Washer & dryer located on first level.

Sep 18 – 25

G$32,141 GYD per night

Guest favorite

Guesthouse in Jamaica

4.95 out of 5 average rating, 133 reviews

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.

Jun 1 – 8

G$20,280 GYD per night

Guest favorite

Cottage in Dover

4.95 out of 5 average rating, 216 reviews

Cozy summer cottage in the woods of southern VT

-The Ice Pond Camp, East Dover, VT. Small well equipped country cottage, surrounded by nature & quaint beauty. Enjoy the lovely Southern Vermont seasons as you relax, disconnect, recharge & spend your days living a slower pace - surrounded by authentic rural beauty. Close to Wilmington and West Dover, (home of Mount Snow) and towns such as Putney and Brattleboro. Just minutes away are scenic villages, green farms, brooks,ponds and lakes, walking trails & country roads.

Jul 19 – 26

G$25,927 GYD per night

Superhost

Apartment in West Townshend

4.91 out of 5 average rating, 313 reviews

Private Apt on Farm, Magnificent views, Hot tub

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. Pls note pricing is based on up to four guests; add'l $25/person/night up to max 5 guests added automatically.

May 5 – 12

G$27,061 GYD per night

Guest favorite

Guest suite in Wilmington

4.92 out of 5 average rating, 713 reviews

Architectural GuestSuite

The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

Sep 20 – 27

G$24,533 GYD per night

Guest favorite

Condo in West Dover

4.94 out of 5 average rating, 181 reviews

Comfy Condo - 2 Min Walk to Carinthia Grommet Lift

One BR condo. Corner unit, 1st floor. 2 min walk to Carinthia Magic Carpet. Minutes drive to golf and mountain biking. 1 BR with Queen bed and full bath with jetted tub. Sofa bed and wood burning fireplace in LR. TV with DVD and Roku in LR. WiFi. Kitchen is small but has everything. Washer/dryer. Storage closet for skis & clubs. Plenty of dining nearby. Perfect for couples, solo adventurers, and small families. Plenty of parking on site.

Nov 7 – 14

G$19,863 GYD per night

Guest favorite

Apartment in Newfane

4.97 out of 5 average rating, 406 reviews

Rock River Retreat: Pets Welcome

You are welcome here with fresh air & room to run - your pet, too, when registered as an extra person! Your private guest suite awaits in a 1790's colonial on the Rock River in the quiet village of South Newfane, VT. Note: Recent floods in Vermont have thankfully not affected our home or guest experience. ❤️ PLEASE READ THE ENTIRE DESCRIPTION BELOW re: kitchenette & pet details.

Jan 28 – Feb 4

G$32,251 GYD per night

Superhost

Cabin in Brattleboro

4.89 out of 5 average rating, 442 reviews

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.

Jun 11 – 18

G$27,467 GYD per night