Guesthouse holiday rentals in Windham County

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!

Location · Value · Backyard

Cottage amongst the trees

Relax in this calm & stylish space. Fully renovated in December 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.

Value · Location · Sleep quality

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.

Value · Location · Amenities

Vermont Alpine Hideaway

Nestled just minutes from the slopes and directly next to town, our mountain retreat is the perfect home base for your next adventure. Whether you're hitting the trails in winter or exploring the Green Mountains in summer, our home has everything you need for a comfortable stay. - 1 Bedroom | Sleeps 4 - 1 Bathroom - 13 min drive to Mount Snow - Walking distance from downtown Wilmington with restaurants and shops Whether you’re here to ski, hike or relax, our home is ready to welcome you!

Value · Family · Walkability

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.

Family · Value · Checkout

Cozy Cottage Loft and Retreat

Our peaceful Vermont cottage is a perfect place to enjoy life, relax and rejuvenate! 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, large copper tub and shower, views of surrounding hills, trees, pond, gardens, your own private entrance and a sweet little trail from right the cottage along Putney Brook. The cozy cottage is a fully separate and private house on our beautiful property.

Location · Condition · Hospitality

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.

Value · Family · Condition

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

Family · Value · Skiing

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 -40 min to Harriman reservoir 2 dog max. Contact us directly to discuss any flexibility here. Parking for 2 cars. NOTE: located on same property as a working farm. You WILL hear roosters & our livestock dog from time to time. 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 house

Family · Value · View

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!

Family · Location · Heating

3 Room Suite, Historic Inn, Jamaicahaus

A 3 Room Suite with lots of light, in Historical Inn with re-imagined amenities. 1 Queen and 1 Pull out trundle bed. Just 12 Minutes from Stratton; the Jamaica house is the turn key solution to your winter Vermont Get-a-way. Imagine all your needs met before you walk in the door. Bring your favorite food to cook and enjoy a social environment with a unique level of privacy.

Location · Value · Cleanliness

House on a hill

Keep it simple at this peaceful and centrally-located large studio home. Enjoy your coffee while sitting on the screened in porch with beautiful local views. Just 3 miles to Brattleboro, VT and 12 miles to Keene, NH you can spend the day hiking in VT and the night in downtown Keene.

Location · Value · Hospitality