
House vacation rentals in Windham County
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Top-rated house rentals in Windham County
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Lovers Honey Pond Treehouse with hot tub & sauna
Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made 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…Enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!! High speed WiFi 🐣

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

Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Lawrence Cottage
Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

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)

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.

Cozy Riverfront Home, 1mi to Mt Snow, On Moover
The Riverhouse at Mount Snow is 1 mile from the mountain (2 min car ride) or take the FREE MOOver. NEW AC. This cozy cabin has open main floor plan and sleeps 6 comfortably with 3 bedrooms, 2 baths, den, living room with wood fireplace. Washer/dryer, gametable, yard games, gas grill, deck overlooking a river with a swimming hole, private firepit area, privacy fence. Easy in/out right off Rt 100 - Walk to restaurants/brewery. Mt. Views from the front porch/yard. 15 Mins from Lake Whittingham.

Modern Cabin with Hot Tub & EV Charging Station
Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Yellow Sweetie at the Base of Stratton
Our adorable home, The Yellow Sweetie, is located in a convenient setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

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.

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.

The Post Haus: one-of-a-kind modern VT experience
Welcome to The Post Haus! A one-of-a kind, modern Vermont mini cabin in the Green Mountain National Forest. This high-end, mid-century mod getaway offers an indoor wood-burning fireplace, sauna, high-end kitchen, and two acres alongside the beautiful Ball Mountain Brook. Come enjoy our truly special piece of Vermont! Pets welcome with a $100 pet fee.
Popular amenities for Windham County house rentals
House rentals with a pool

Stratton/Mt Snow minutes away! Hot tub + Game room

MtSnow/Stratton Ski Lodge-Hot Tub-Game Room-Pool

Silver Moose Lodge (Mt Snow)

Adams Farm-"The Little Farmhouse"

Woodsy Retreat Near Skiing, Private Pool in Summer

Hot Tub + Clubhouse Pool | 10 min Mt Snow

Winter Skiing @ Mt Snow! Ski off trail sleeps 8.

Chimney Hill Haven | Close to Mt.Snow
Weekly house rentals

Bright & Vibrant Mountain Home

Tranquil VT Ski House Retreat

Highland Haus: stunning ski getaway with hot tub

Your Own Hot Tub, Game Room, Traeger 15Min2 MtSnow

Ski & Play in Style-Luxury Mt. Snow Getaway-HotTub

Scandinavian Serenity Close to Okemo

Peaceful Beautiful Mountain Home Spectacular Views

FULLY renovated 1 bed/1 bath ski in-out condo!
Private house rentals

Yellow Door: Welcoming Couples & Solo Guests

Coverd Bridge Cabin

Briar Ridge - Beautiful 4 Bedroom Ski Home

Pristine Magical Retreat Cottage 15 min to Mt Snow

Boulder House

Gorgeous Vermont Lakefront with epic sunsets!

Pettengill Schoolhaus scenic 2 min to main village

Stratton walk on/ski off, Kings, hot tub, shuttle
Destinations to explore
- Rentals with a hot tub Windham County
- Rentals with lake access Windham County
- Rentals with breakfast Windham County
- Beachfront rentals Windham County
- Rentals with pools Windham County
- Rentals with a kayak Windham County
- Boutique hotels Windham County
- Hotel rooms Windham County
- Aparthotel rentals Windham County
- Family-friendly rentals Windham County
- Rentals with beach access Windham County
- Fitness-friendly rentals Windham County
- Rentals with a washer and dryer Windham County
- Bed and breakfasts Windham County
- Waterfront rentals Windham County
- Apartment rentals Windham County
- Private suite rentals Windham County
- Townhouse rentals Windham County
- Pet-friendly rentals Windham County
- Chalet rentals Windham County
- Guesthouse rentals Windham County
- Tiny house rentals Windham County
- Condo rentals Windham County
- Rentals with an accessible height toilet Windham County
- Rentals with a fire pit Windham County
- Rentals with a sauna Windham County
- Cabin rentals Windham County
- Rentals with a fireplace Windham County
- Rentals with a patio Windham County
- Farmstay rentals Windham County
- Ski-in/ski-out rentals Windham County
- Rentals with outdoor seating Windham County
- Rentals with an EV charger Windham County
- House rentals Vermont
- House rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Mount Sugarloaf State Reservation
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Hildene, The Lincoln Family Home
- Peebles Island State Park
- Dorset Field Club
- Hooper Golf Course
- Fox Run Golf Club
- National Museum of Racing and Hall of Fame
- Northern Cross Vineyard
- Willard Mountain
- The Shattuck Golf Club




