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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, 123 reviews

Fall Foliage in Beautiful 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

4.92 out of 5 average rating, 104 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, 161 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, 365 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, 182 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

4.96 out of 5 average rating, 185 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 Wilmington

4.94 out of 5 average rating, 254 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, 203 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).

Home in Dover

4.87 out of 5 average rating, 235 reviews

Mt Snow retreat, ski & summer

Warm and welcoming space for relaxation and play, your home base for VT recreation. 7 min. drive to Mount Snow, convenient location. Easy access to hiking, mountain biking, x-c skiing, golf course, and more! Sleeps 5 easily. ~10 min. walk to Moover, 7-11, restaurants. INTERNET - There is a fiber optic connection and the plan speed is 50Mbps down / 30Mbps up.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Cabins

Kick off your hiking boots at these rustic lodgings

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, 40 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, 162 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

4.83 out of 5 average rating, 36 reviews

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

Home in Dover

5 out of 5 average rating, 34 reviews

3bd Mt.Snow condo: with ski off trail Booking Fast

Home in Wilmington

4.83 out of 5 average rating, 162 reviews

The Vermont Barn (Mount Snow)

Home in Peru

4.91 out of 5 average rating, 152 reviews

Beautiful Bromley/Manchester VT Retreat w/hot tub

Weekly house rentals

Home in Newfane

4.94 out of 5 average rating, 88 reviews

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

Home in Jamaica

5 out of 5 average rating, 29 reviews

2-Bedroom Home, 7 Minutes From Stratton Mountain

Home in Jamaica

4.9 out of 5 average rating, 78 reviews

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

Home in Wardsboro

4.95 out of 5 average rating, 95 reviews

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

Home in Stratton

4.84 out of 5 average rating, 88 reviews

Stay mins from Mt. Snow & Stratton w/ EV charger

Home in Dover

5 out of 5 average rating, 11 reviews

HotTub/Pool/Ping/Bball/11 min. to Mt. Snow/ Family

Home in East Dover

5 out of 5 average rating, 35 reviews

Magical Retreat Cottage - Vermont cabin getaway

Home in Putney

4.89 out of 5 average rating, 100 reviews

Peaceful Beautiful Mountain Home Spectacular Views

Private house rentals

Home in Dover

4.95 out of 5 average rating, 42 reviews

Leaf Peeping MidWeek Special @ Ellis Brook Retreat

Home in Wardsboro

4.93 out of 5 average rating, 28 reviews

Riverside Chalet near Mt. Snow & Stratton resorts

Home in Dover

5 out of 5 average rating, 10 reviews

Mount Snow Getaway

Home in Putney

4.94 out of 5 average rating, 16 reviews

19th Century Farmhouse Retreat

Home in Chesterfield

4.96 out of 5 average rating, 52 reviews

The River House

Home in Brattleboro

5 out of 5 average rating, 12 reviews

Sauna with Mountain Views: Perfect Vermont Getaway

Home in Wardsboro

4.94 out of 5 average rating, 32 reviews

Cozy Vermont getaway near Mount Snow & Stratton

Home in Wilmington

5 out of 5 average rating, 17 reviews

Newly renovated chalet, 9 min to Mt. Snow

Destinations to explore