We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

House vacation rentals in Windham County

Find and book unique houses on Airbnb

Top-rated house rentals in Windham County

Guests agree: these houses are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Home in Readsboro

4.86 out of 5 average rating, 124 reviews

Relax in Peaceful Vermont! (Pet Friendly)

Beautiful Country Home, nestled in Vermont's Green mountains, panoramic views, with good access by the road. A babbling brook to lull you asleep from the master bedroom, and a clawfoot soaking tub, fully stocked house. Hiking, antiques, shops, lakes, picnics, covered bridges, cozy local inns, mountain views! Enjoy Vermont! Scenic roads, Mt. Snow, VAST trails, Mt.Greylock, Mass MOCA museum, nearby N.Adams, MA, Berkshires. Bennington Wilmington & Mt. Snow. PEACEFUL & PERFECT Vermont getaway! ☺

Home in Putney

4.88 out of 5 average rating, 168 reviews

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)

Home in Putney

4.94 out of 5 average rating, 367 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.

Home in Winhall

4.95 out of 5 average rating, 190 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Just minutes to skiing at Stratton Mountain, Bromley and Magic. Explore 27+ acres of forest with trails, river, sculpture gardens and private pond. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. A short drive to Manchester with shops and restaurants. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Home in Chesterfield

4.9 out of 5 average rating, 102 reviews

Governer's Brook Camp - 2 Bedroom

Renovated camp, 800 sq ft, betweeen Brattleboro VT & Lake Spofford NH. Hiking trails start at the backyard. It’s 15 minutes to Brattleboro, 5 minutes to the boat ramp on the Connecticut River, 15 minutes to Lake Spofford, and 50 minutes to Mt. Snow. Across the road is a (seasonal) tumbling waterfall and gorge called “the Devils Den”. The backyard leads to woodlands with miles of trails. Enjoy a relaxing evening by the firepit overlooking the brook. Or outdoor cooking on a propane grill.

Home in South Londonderry

4.84 out of 5 average rating, 128 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

This VERY NEW and VERY romantic treehouse is finished!!! The Honey Pond Treehouse is made especially for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…You will enjoy private hot tubbing, sauna time, relaxing, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes…biking & disc golf at Magic Mnt!

Home in West Brattleboro

4.87 out of 5 average rating, 141 reviews

Cozy Home for 2-5 People in Vermont

Comfortable house for 2 to 4 people (two queen-sized beds) and a pull-out couch for a 5th person and a self-inflatable bed. Located in a quiet neighborhood. There are two main bedrooms with queen beds in each. There is also a pull-out couch in the room with the fireplace though it is not as comfortable as the self-inflatable bed (and deflatable) in the house. Fast Wi-Fi from Xfinity. Easy to get into Brattleboro Center and an excellent location for exploring Southern Vermont.

Home in Newfane

4.98 out of 5 average rating, 130 reviews

Peaceful cabin close to skiing & Brattleboro

Our 4BR/2BA (+ outdoor summer shower) home embraces the best of Southern VT. Skiing (20 min to Mt. Snow; 35 min to Stratton), river swimming holes, hiking, biking, art galleries and great restaurants nearby. Open concept space, cook's kitchen, jet bathtub, beautiful gardens, winter hot tub off deck, and large patio and fireplace give a homey feel. Secluded from neighbors but close to amenities, this home is a comfortable and peaceful retreat for your next gathering.

Home in Wilmington

4.94 out of 5 average rating, 258 reviews

Wilmington. Easy walk to center of town.

Beautifully renovated bright, 120year old home in town. House thoroughly cleaned and sanitized after each stay. Touchless flushing toilets. Mini-Split air conditioning in each bedroom and on the main level. Minutes to MT Snow. Easy walk to town for food and shopping. Deerfield river directly across the street. 2 min from the lake. Valley hiking trails within sight. There is a 2 car limit. A request for additional vehicles needs to be made prior to check-in.

Home in Townshend

4.94 out of 5 average rating, 205 reviews

Comfy and Cozy House on 67 acres

67 acre of wilderness to explore, a calm and relaxed getaway. Bright, spacious main room and open kitchen with wood stove is enclosed by the large porch which looks over the Vermont woodlands. Right off of the large entryway, you'll find the sweeping main bedroom equipped with an open soaking tub, and a second wood stove, along with a separate entrance. Finally, there is a separate bedroom downstairs with its own bathroom (off of garage).

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Windham County house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Wardsboro

5 out of 5 average rating, 43 reviews

Minutes to Mt. Snow/Stratton! Hot Tub + Game Room

Home in Wilmington

5 out of 5 average rating, 12 reviews

Silver Moose Lodge (Mt Snow)

Home in Wilmington

5 out of 5 average rating, 8 reviews

Outdoor Enthusiasts Paradise!

Home in Wilmington

4.88 out of 5 average rating, 163 reviews

Adams Farm-"The Little Farmhouse"

Home in Dover

5 out of 5 average rating, 54 reviews

The Villa - Industrial Farmhouse with Hot Tub

Home in Wilmington

5 out of 5 average rating, 11 reviews

Stylish Chimney Hill Home - Close to Mt. Snow!

Home in Wilmington

4.82 out of 5 average rating, 38 reviews

Mountain Paradise 4 Bed w/ Hot Tub Mins to Mt Snow

Home in Dover

4.97 out of 5 average rating, 39 reviews

3bd Mt.Snow condo: Fireplace and ski off trail.

Weekly house rentals

Home in Newfane

4.94 out of 5 average rating, 89 reviews

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

Home in Dover

4.96 out of 5 average rating, 46 reviews

Good Vibes & Comforts of Home @Ellis Brook Retreat

Home in Jamaica

5 out of 5 average rating, 31 reviews

2-Bedroom Home, 7 Minutes From Stratton Mountain

Home in Jamaica

4.9 out of 5 average rating, 81 reviews

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

Home in Windham

4.87 out of 5 average rating, 101 reviews

Magic Creek

Home in East Dover

5 out of 5 average rating, 37 reviews

Magical Retreat Cottage - Vermont cabin getaway

Home in Londonderry

4.97 out of 5 average rating, 130 reviews

Wild Blossom Farmhouse - a lovely family getaway

Home in Brattleboro

4.87 out of 5 average rating, 194 reviews

Cozy Cabin Retreat on the River

Private house rentals

Home in Putney

4.97 out of 5 average rating, 31 reviews

Historic Putney Home

Home in Wardsboro

4.93 out of 5 average rating, 30 reviews

Riverside Chalet near Mt. Snow & Stratton resorts

Home in Dover

4.94 out of 5 average rating, 79 reviews

Cozy Riverfront Home, 1mi to Mt Snow, On Moover

Home in Wardsboro

4.95 out of 5 average rating, 97 reviews

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

Home in Marlboro

4.99 out of 5 average rating, 97 reviews

Large home in scenic Marlboro

Home in Dover

5 out of 5 average rating, 12 reviews

11 min. to Mt. Snow Family HotTub/GameRm/FirePit

Home in Dover

4.92 out of 5 average rating, 75 reviews

New Hot Tub! Gas Fireplace! 2 min to Mt Snow

Home in Whitingham

4.99 out of 5 average rating, 80 reviews

Lakefront with Spectacular Sunset/Mountain Views

Destinations to explore