House holiday rentals in Windham County

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Top-rated house rentals in Windham County

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Guest favourite

Home in Grafton

4.94 out of 5 average rating, 122 reviews

The Grafton Chateau

Welcome to the Grafton Chateau, a gorgeous secluded and private country retreat for all of your family and friends. With six bedrooms and a den, four baths, two fireplaces, a sauna and a large private pond beautifully situated on 67 acres of woodlands, the Grafton Chateau is the perfect comfortable home base for ski trips, hiking, antiquing, or just enjoying the scenery while you sit around the fire pit. The garage has outdoor recreation gear, like snowshoes and sleds. The den has a variety of toys, and games for kids and adults. The whole house, sauna house, barn and all 67 acres are all yours! We are always available by phone, text, or email if you have any questions. Grafton is just about the most charming Vermont town you can find and is convenient to four ski mountains and every other outdoor activity you can imagine.

Top guest favourite

Home in West Brattleboro

4.93 out of 5 average rating, 119 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

Guest favourite

Home in Townshend

4.97 out of 5 average rating, 120 reviews

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.

Top guest favourite

Home in Putney

4.94 out of 5 average rating, 399 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.

Top guest favourite

Home in Wilmington

4.99 out of 5 average rating, 208 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.

Guest favourite

Home in Winhall

4.96 out of 5 average rating, 257 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

Top guest favourite

Home in Newfane

4.98 out of 5 average rating, 137 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.

Guest favourite

Home in Wilmington

4.94 out of 5 average rating, 279 reviews

Wilmington. In Town Village Home

Beautifully renovated bright, 125 year 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.

Guest favourite

Home in Brattleboro

4.94 out of 5 average rating, 221 reviews

Frosted Willows

Your family will be close to everything at this sunny, centrally located home on the Whetstone Brook. Just 0.6 miles from downtown Brattleboro, you can walk to shops, cafés, galleries, and more. Nestled in a quiet neighborhood, the house offers a peaceful place to relax after a day of exploring. Listen to the brook from the backyard, enjoy local adventures, and settle into a space that feels like home—perfect for a weekend getaway or a longer Vermont stay.

Guest favourite

Home in Putney

4.9 out of 5 average rating, 105 reviews

Peaceful Beautiful Mountain Home Spectacular Views

15 Spectacular Acres! Plenty of room for the entire family or great for a couples getaway. This home has everything you need. There are brand new mattresses, quilts, linens, towels, cookware, plates and utensils for your comfort. The beautiful mountain views are seen from just about every room. There is a wood burning fireplace, 4 bedrooms and 2 full bathrooms. Both levels have 3 season porches to enjoy the views, coffee, reading or a meal.

Guest favourite

Home in Winhall

4.98 out of 5 average rating, 387 reviews

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.

Guest favourite

Home in Jamaica

4.92 out of 5 average rating, 100 reviews

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.