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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Guest favorite

Guesthouse in Marlboro

4.99 out of 5 average rating, 141 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!

Oct 13 – 20

$220 per night

Guest favorite

Guesthouse in Wilmington

5.0 out of 5 average rating, 23 reviews

Cozy, charming cottage 7 mins from Mount Snow

Take a deep breath and relax at this cozy mountain cottage. Less than 10 minute drive from both Mt. Snow & Harriman Reservoir/Lake Whitingham, it's an idyllic getaway all year round. You'll stay in the cottage shown in the pictures, which is the guest house next to the main cottage. -Nespresso w/ lots of coffee options -Aesop shower products -65in 4K TV w/ Sonos surround sound system -Fiber WiFi -Peloton -Weber grill with side burner -Sustainably sourced furniture -Local art & handmade goods

Sep 23 – 30

$188 per night

Guest favorite

Guesthouse in Brattleboro

4.99 out of 5 average rating, 199 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.

Jul 8 – 15

$114 per night

Superhost

Guesthouse in Town of Rockingham

5.0 out of 5 average rating, 11 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.

Aug 19 – 26

$147 per night

Guest favorite

Guesthouse in Jamaica

4.95 out of 5 average rating, 133 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.

Jun 6 – 13

$84 per night

Guest favorite

Guesthouse in Dover

4.94 out of 5 average rating, 48 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.

Sep 20 – 27

$198 per night

Guest favorite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 432 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.

Jul 6 – 13

$88 per night

Guest favorite

Guesthouse in Grafton

4.89 out of 5 average rating, 91 reviews

VT Sugar House-Guesthouse

Looking to ski/snowboard at Okemo, Stratton or Magic Mountain and need a place to stay? The Vermont Sugar House offers a perfect combo of hotel and camp life but with AC/ heat and wifi, but note there is no running water. Enjoy private accomodations with a comfortable night's sleep in a fluffy white bed, watching Netflix from the mounted smart TV. Lounge in comfortable fresh robes, play a board game or WFH. Located 5 min from the cute main street of Grafton.

Nov 3 – 10

$63 per night

Guest favorite

Guesthouse in Jamaica

4.86 out of 5 average rating, 56 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. 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!"

May 4 – 11

$102 per night

Guest favorite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 59 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!

Jun 26 – Jul 3

$139 per night

Guest favorite

Guesthouse in Wilmington

4.91 out of 5 average rating, 57 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

Jul 12 – 19

$165 per night

Guest favorite

Guesthouse in Putney

4.97 out of 5 average rating, 198 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.

Mar 21 – 28

$90 per night