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House vacation rentals in Windham County

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Top-rated house rentals in Windham County

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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 West Brattleboro

4.93 out of 5 average rating, 108 reviews

Modern Spacious Home with Mountain Views

Modern Home in Brattleboro with mountain view & many extras: Italian-Marble master-suite, Jacuzzi/Shower for 2, walk-in closet, king bed, grill, heated garage, cable, WiFi. Open-concept living room w/ cathedral ceiling, office, & movie screen. Large open kitchen w/ wine fridge. Second bedroom w/ loft. Explore hiking trails from backyard. Pets ok! 3 mins from Vermont Country Deli & I91 Exit 2. Walking distance to dog park, swimming holes. Downtown: 4 mins Mount Snow: 40 mins Stratton: 54 mins

Home in Putney

4.88 out of 5 average rating, 171 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, 369 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 Wilmington

4.99 out of 5 average rating, 188 reviews

Vermont Sugar House Retreat

Stay at this unique rustic Vermont getaway. Nestled on a quiet hill in Wilmington, this private retreat will serve as the perfect home base for your Vermont adventures. You'll have the house to yourself without a neighbor in sight. While very private and surrounded by beautiful forest, this house is still only a short 5 minute drive from downtown Wilmington. The house is built around an enormous one-of-a-kind natural stone fireplace that was formed atop the old foundations of a sugar house.

Home in Winhall

4.95 out of 5 average rating, 195 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, 103 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 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 Wardsboro

4.95 out of 5 average rating, 100 reviews

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

Welcome to Three Bears Mountain House - your Southern Vermont getaway! We're located 10 minutes from Mount Snow and 15 minutes from Stratton. We designed our cabin to be inviting and cozy, a place you'll never want to leave. Come for a fun-filled weekend on the mountains skiing or a relaxing getaway in nature. End your day with a relaxing soak in our 7-person hot tub. Visit the local breweries and farms for an authentic Vermont experience!

Home in Townshend

4.94 out of 5 average rating, 206 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

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

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, 45 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

4.88 out of 5 average rating, 163 reviews

Adams Farm-"The Little Farmhouse"

Home in Newfane

4.92 out of 5 average rating, 48 reviews

6 BR Perfect Private Retreat in Vermont!

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, 12 reviews

Stylish Chimney Hill Home - Close to Mt. Snow!

Home in Dover

4.98 out of 5 average rating, 40 reviews

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

Home in Wilmington

4.83 out of 5 average rating, 42 reviews

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

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

4.9 out of 5 average rating, 69 reviews

Timber Frame Contemporary w/ Hot Tub at Mount Snow

Home in Jamaica

5 out of 5 average rating, 32 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 East Dover

5 out of 5 average rating, 38 reviews

Magical Retreat Cottage - Vermont cabin getaway

Home in Townshend

4.95 out of 5 average rating, 77 reviews

Cozy, Comfy Country Home in Southern VT Village

Home in Newfane

4.98 out of 5 average rating, 66 reviews

Riverside Farmhouse

Home in Wardsboro

4.86 out of 5 average rating, 22 reviews

The Perch

Private house rentals

Home in Putney

4.97 out of 5 average rating, 32 reviews

Historic Putney Home

Home in Dover

4.96 out of 5 average rating, 49 reviews

Good Vibes & Comforts of Home @Ellis Brook Retreat

Home in Dover

4.93 out of 5 average rating, 82 reviews

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

Home in Dover

5 out of 5 average rating, 90 reviews

Large, beautiful home just 2 minutes to Mount Snow

Home in Whitingham

4.97 out of 5 average rating, 91 reviews

Ski Season! Play Area, Crib, 11 Acre Farmhouse

Home in Dover

4.95 out of 5 average rating, 73 reviews

Contemporary 4-BR Alpine Chalet 10-min to Mt. Snow

Home in Dover

5 out of 5 average rating, 12 reviews

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

Home in Brattleboro

5 out of 5 average rating, 14 reviews

Sauna with Mountain Views: Perfect Vermont Getaway

Destinations to explore