Guesthouse vacation rentals in Windham County

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Top-rated guesthouse rentals in Windham County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A stone patio area with a dining table and chairs invites relaxation outdoors. The guesthouse features large windows that provide views of the surrounding woodland. Lush greenery and natural light create a serene setting, complemented by a nearby path leading to the garden.

Guesthouse in Marlboro Township

4.97 out of 5 average rating, 160 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 favorite

Guesthouse in Jamaica

4.86 out of 5 average rating, 69 reviews

5 min to Stratton, pet friendly, fire pit

-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 feel free to check out our brand new tiny home! Located on the same property. The title is "Tiny home w/fireplace, 5 min drive from Stratton!

Superhost

A light yellow cottage is positioned on a grassy expanse, featuring black shutters and a grey roof. The structure has a porch with chairs, surrounded by lush greenery and large trees. A historic estate can be seen adjacent to the cottage.

Guesthouse in Town of Rockingham

4.87 out of 5 average rating, 39 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.

Guest favorite

Guesthouse in Brattleboro

4.98 out of 5 average rating, 228 reviews

Light Filled Loft in the Vermont Countryside

Our spacious, tranquil, light-filled Barn Loft is thoughtfully and creatively designed. Complete with a living area, sleeping alcove, flat-screen TV, full kitchen, dining area, and large bathroom with a deluxe shower. A private deck with seating that looks out into our lovely Vermont woods and verdant gardens is attached to the loft. Stay a night or a week, there is plenty to do in every season. We are a friendly, welcoming, worldly, family. We look forward to hosting you at our country home.

Top guest favorite

Guesthouse in Dummerston

5 out of 5 average rating, 10 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 favorite

An open-air shower area is surrounded by wooden fencing, featuring a bench made of natural wood. The stepping stone floor is interspersed with smooth pebbles, and a green grassy area can be seen just beyond the enclosure.

Guesthouse in Jamaica

4.95 out of 5 average rating, 155 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 favorite

An inviting log cabin structure showcases traditional architecture with a stone foundation and a balcony adorned with wooden railings. A flag is displayed, and a gravel driveway leads to a detached garage, surrounded by lush greenery and mature trees.

Guesthouse in Dover

4.95 out of 5 average rating, 64 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.

Superhost

A beautiful retreat is set amidst lush greenery, featuring a wooden structure with a welcoming entrance. A stone pathway leads through the garden, and the building is surrounded by various plants, enhancing the natural ambiance of the setting.

Guesthouse in Brattleboro

4.91 out of 5 average rating, 515 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 favorite

A charming red cottage is surrounded by lush green grass and trees. A wooden deck extends from one side, while a calm seating area with white chairs is positioned on the lawn. The clear blue sky complements the serene outdoor environment.

Guesthouse in Wilmington

5 out of 5 average rating, 35 reviews

Cozy, charming cottage 7 mins from Mount Snow

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 favorite

A view from the interior through large sliding doors reveals a spacious deck overlooking a serene garden. Vibrant foliage, including a red maple tree, frames the scene. The exterior space includes a seating area and a pathway leading to neighboring structures.

Guesthouse in Brattleboro

4.93 out of 5 average rating, 70 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

An open-concept living area is visible, featuring wooden beams and a rustic stone wall. A kitchen counter with a granite surface is positioned in the foreground, while a cozy seating area with multiple chairs and a sofa is arranged in the background, illuminated by natural light.

Guesthouse in Wilmington

4.89 out of 5 average rating, 73 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 favorite

A wooden deck extends from the cottage, offering a view of a vibrant sunset illuminating the sky in warm hues. Snow blankets the ground, while trees line the meadow, enhancing the serene landscape. A pathway leads into the white expanse, inviting exploration.

Guesthouse in Guilford

5 out of 5 average rating, 34 reviews

Peaceful forest cottage weekend getaway

Cozy one bedroom cottage with full 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.