Guesthouse holiday rentals in Windham County

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Top-rated Guesthouses in Windham County

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Marlboro Township

4.97 out of 5 average rating, 169 reviews

Refined, serene and like no other, Marlboro, VT.

Our elegant, supremely comfortable, and private guesthouse is surrounded by a wonderful garden and 350 acres of woodland in the quiet of rural Vermont. We are 30 minutes from Brattleboro to the east, with its many shops and restaurants, and 12 minutes from the small town of Wilmington to our west, with some restaurants, shops, and a supermarket However, we always recommend bringing groceries, etc., for your first night and next morning. We are pleased to offer a 20% discount for 7 days or more!

Guest favourite

Guesthouse in Town of Rockingham

4.89 out of 5 average rating, 46 reviews

Peaceful Historic Cottage

Picturesque private two bedroom cottage attached to historic estate, located within the village of Saxtons River. Walking distance to the quaint downtown, Vermont Academy and an extensive network of hiking trails. Short drive to several Southern Vermont attractions including Okemo and the Vermont Country Store. The grounds boast 6 acres of sprawling gardens, an orchard and fire pit perfect for star gazing. Experience this special property which has been owned by the same family for 200 years.

Top Guest favourite

Guesthouse in Dummerston

5 out of 5 average rating, 19 reviews

Cottage amongst the trees

Relax in this calm & stylish space. Fully renovated in late 2024, this tiny house sits on 14 acres of land overlooking a seasonal pond, gardens & patios. Hosts live in the main house built in 1803. Great for the travelling professional who is looking for a peaceful & comfortable place to unwind after a long shift at the hospital or day on the slopes. Minutes to downtown Brattleboro yet in a rural setting. Equidistant to exits 3 or 4 on I-91; close to Putney, Bellows Falls, Keene & Mt. Snow.

Top Guest favourite

Guesthouse in Jamaica

4.95 out of 5 average rating, 170 reviews

The Chick Inn

This is a two-story, renovated barn adjacent to the chicken coop in rural Vermont with views of the forests. It has brand new floors, a new kitchenette, and fresh look. (Some renovation is still taking place.) The chicken coop is just next door but the birds are free-range and range they will. Enjoy a private, hot shower in the garden, just outside. This listing is only suitable for people comfortable with dogs, cats, and chickens which will undoubtedly greet you outside during your stay.

Top Guest favourite

Guesthouse in Dover

4.96 out of 5 average rating, 69 reviews

Mount Snow-Cozy 2BR-The Streif

Enjoy your Green Mountain getaway at our cozy & private 2 bedroom guesthouse located less than one mile from Mount Snow’s North Access Road. All the amenities you need for a relaxing and comfortable Vermont escape including: a full kitchen with breakfast bar, gas fireplace, WiFi high speed internet, 2nd floor deck with beautiful mountain views, backyard patio & fire pit, private hiking/cross country skiing trails, direct VAST snowmobile trail access, all the privacy you need and much more.

Guest favourite

Guesthouse in Brattleboro

4.91 out of 5 average rating, 552 reviews

Mahalo Temple Retreat

Retreat in Mahalo's beautiful, private sound healing temple surrounded by nature, amongst streams, berry bushes, fruit & nut trees, medicinal plants and veggie gardens. We are set back just enough from a main road to find your serenity and yet close enough to civilization for human interaction and trails for hiking. Quiet and peaceful location just a few min off I-91 and just over 2 miles from the center of Brattleboro. A fun and quirky town with art cafes, restaurants, and great shops.

Top Guest favourite

Guesthouse in Wilmington

5 out of 5 average rating, 44 reviews

Cozy, charming cottage 7 mins from Mt Snow & Lake

Take a deep breath & relax at this cozy, design-forward mountain cottage. Less than 10-minute drive from both Mt. Snow and two lakes, it's an idyllic getaway all year round. You'll stay in the guest cottage next to the main house. -Bunk bed handmade locally -Three outdoor fire pits -Nespresso w/ lots of coffee options -Aesop products -65in 4K TV w/ Sonos surround sound system -Fiber WiFi -Peloton -Weber grill with side burner -Sustainably sourced furniture -Local art & handmade goods

Guest favourite

Guesthouse in Jamaica

4.86 out of 5 average rating, 76 reviews

Stratton; 5 min. Pikes Falls, 1 min. Pets welcome!

-5 min drive to Stratton Mnt -3 min WALK to Pikes Falls -18 min to Bromley -25 min to Manchester -30-40 min to Okemo, Mount Snow, Magic -40 min to Harriman reservoir Pets allowed. 2 dog max. Contact us directly to discuss any flexibility here. PLEASE NOTE: ALL DOGS MUST BE ON A LEASH IN THE YARD. Parking for 2 vehicles. If your dates are unavailable please reach out and/or check out our other properties. We have everything from an awesome Tiny Home to 5+ bedroom ski/on off houses.

Guest favourite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 75 reviews

Casita by the Green: Quiet, Country, close to town

The Casita is a fully-equipped guest house, by the Country Club green, on a park-like acre backed by a farm. The big bedroom gives view to a lovely back garden w/tall pines. The private bath has shower & clawfoot tub. Spacious Big Room has separate kitchen, dining table and a large sitting area. The slider goes to your own deck facing a sun-dappled back garden. Peace and quiet. But right by town -- so you're a quick hop from everything!

Superhost

Guesthouse in Wilmington

4.83 out of 5 average rating, 80 reviews

New! remodeled Barn. min from Lake, Ski, Hot tub

Just remodeled old barn with original wood beams and floors. All new Kitchen/bathroom/furniture and appliances. Attached to main house but private entrance and driveway. Minutes from the beautiful town of Wilmington. 15 Minutes from MT snow Skiing and 5 minutes to beautiful Wards beach at Lake Whitingham. New Hot tub and deck to enjoy the after a long hike or watching the amazing stars. Just added a firepit. wood provided

Top Guest favourite

Guesthouse in Guilford

5 out of 5 average rating, 50 reviews

Peaceful forest cottage getaway

Cozy one bedroom cottage with kitchen overlooking a forest meadow. Walking paths along a lovely brook. Owner lives in a separate residence 100 feet up the hill and may be seen outside in the meadow, garden or shared driveway. There is a pull out queen sofa bed in the living room in addition to the queen bed in the bedroom, although the cottage is most comfortable for 1 or 2 guests.

Top Guest favourite

Guesthouse in Putney

4.98 out of 5 average rating, 345 reviews

Cozy cottage loft and retreat

Relax and recharge in our peaceful Vermont cottage. Enjoy this sweet getaway with hardwood floors, fast wifi, a fully equipped kitchen, a quiet sleeping loft with a queen size bed, gorgeous natural light, views of surrounding hills and pond, gardens, and your own private entrance and back deck next to the Putney Brook.