Holiday rentals in Windham County

4.94 out of 5 average rating, 395 reviews

Home in Putney

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.

5 out of 5 average rating, 245 reviews

Cabin in Jamaica

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

4.95 out of 5 average rating, 156 reviews

Guest house in Jamaica

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.

4.99 out of 5 average rating, 183 reviews

Tiny home in Dover

Rustic Cabin in foothills of Green Mountains

Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials+ hosts provide water, coffee, tea, milk, fresh eggs + homemade soap. There is an indoor compostable toilet + outhouse + outdoor shower. Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

4.82 out of 5 average rating, 271 reviews

Cottage in Putney

The Cottage, a house built for guests.

In the village there is a wonderful farm to table restaurant, the Gleanery. A local pub, friendly, great food with indoor and outdoor dining & pub. The General Store, is the oldest continually run general store in Vt. The Next Stage, Yellow Barn, Sandglass Theater, these places provide an amazing collection of visual, musical, spoken word and world renowned art and artist to experience. These cultural event locations are but a mile away for the Cottage I hope you choose for your stay.

4.84 out of 5 average rating, 305 reviews

Cottage in Dover

Cozy Camp in Vermont

This cozy camp located in beautiful East Dover, is on a secluded road off the beaten path. Close to Mount Snow, Lake Whitingham, Lake Raponda, and only 25 minutes to Brattleboro the adventures are endless! Get out of the city and visit the serenity and beauty of Southern Vermont- especially in Fall during “leaf peeping”. This is a camp-style cottage with rustic charm. Newly replaced flooring and a fresh coat of paint in both bedrooms upstairs. Snow tires are a MUST- Nov.-April

Campervan/Motorhome in Guilford

4.93 out of 5 average rating, 141 reviews

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for up to two adults and one kid (63" long fold down couch).

4.94 out of 5 average rating, 1,269 reviews

Tiny home in Jamaica

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

4.93 out of 5 average rating, 353 reviews

Apartment in Brattleboro

Private & Quiet Studio Apt. in Vermont

Clean, comfortable , quiet and snug, this studio apartment is a great place to come and relax in. It has a comfy QUEEN size bed with a 40” LCD at its foot, a kitchen set up for cooking and a desk with a view of a green field. This apartment is situated on the ground floor of our detached garage. Our garage sits behind our home, well away from the street. We live in a residential neighborhood that is conveniently located near I91, Route 30, Route 9 and Downtown .

4.87 out of 5 average rating, 146 reviews

Flat in Newfane

Apartment at Five Ferns

A cozy spot perfect for quick romantic getaways and an equally comfortable base for longer adventures. Views out your windows show perennial flower gardens and trees. Queen mattress in a spacious bedroom, en-suite bathroom (shower), and a living/dining area with an equipped kitchen are all at your service. Enjoy our yard and trails along the river. We are an easy 5 minute drive to a fantastic restaurant and many more within 15 minutes of driving.

4.97 out of 5 average rating, 151 reviews

Barn in Newfane

Beautiful rustic woods and fields retreat.

Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment. Part of a renovated 19th century barn it is the perfect getaway. It sits on over 33 acres of fields, woods, apple orchard and Mountain View’s. 2 miles from historic Newfane Vermont, you are able to enjoy privacy, while close to the many attractions of the area. We are also dog friendly. There is an extra fee of $80 per trip per dog

4.93 out of 5 average rating, 210 reviews

Guest suite in Newfane

Cute studio apt on historic VT farm

Spend some time on a historic farm in Southern Vermont. Visit with pigs and chickens, walk around on country roads, take a dip in swimming holes, wildlife abounds! Super-relaxing setting in beautiful Mother Nature and well-equipped accommodations with everything you need. The self-contained little studio has a separate entrance. Full kitchen and bath, queen bed plus a roll-out twin. Excellent heater. Starlink wifi.

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Windham County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Windham County

4.9 out of 5 average rating, 20 reviews

Guest suite in Dover

The Eagles Nest - Private Apartment

CorentinRating, 5 stars1 week ago

This place was absolutely stunning; beautifully decorated, warm, and thoughtfully designed. The hosts were incredibly kind and accommodating. They welcomed us with cookies and even surprised us with more before we left; placed thoughtfully on our car. They also allowed us a late checkout, which made the experience feel even more cared for. We felt truly held here and would absolutely come back.

4.96 out of 5 average rating, 71 reviews

Cabin in Guilford

Guilford Grove Cottage

ElizabethRating, 5 stars6 days ago

We truly loved staying in this beautiful, cozy cabin. It was just the right size for the two of us, and very comfortable. The view of trees and wildflowers was lovely and refreshing. It was also fun to have a couple of cats walk across the porch each day! Joel was very proactive and friendly, which we greatly appreciated.

Guest house in Marlboro Township

4.97 out of 5 average rating, 160 reviews

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

Matthew EvanRating, 5 stars5 months ago

Jill and T. were amazing hosts, quite possibly the nicest and all around best that I've experienced. They were attentive and incredibly kind, and together have a presence to them that makes you feel comfortable and right at home. They also were a wealth of knowledge about the surrounding area, the property, and the trails that are accessible right down the road from the guest house. The guest house itself is across the large driveway from the main house, and while close, it feels properly secluded and private. Inside, it is impeccably furnished with the styling and taste that only someone well traveled could do so well: books about sculptors, poetry, classics, Vermont history. Beautiful furniture and an inviting layout of the space. The furnishings, books, kitchen setup, and many places to sit and relax, were as much part of the greatness as the nature surrounding it. I will absolutely come back here for the relaxation, the amenities, and also the lovely hosts.

5 out of 5 average rating, 50 reviews

Home in East Dover

Magical Retreat Cottage - Waterfalls Everywhere

DavidRating, 5 stars1 day ago

Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.

4.94 out of 5 average rating, 17 reviews

Cabin in Brookline

Off-the-Grid Cabin in the Forest

AndrewRating, 5 stars2 weeks ago

Ideal cabin in the woods for a secluded forest getaway - well stocked kitchen, and the outhouse is 10/10. Very responsive and helpful!

Guest house in Brattleboro

4.92 out of 5 average rating, 528 reviews

Mahalo Temple Retreat

LilaRating, 5 stars2 weeks ago

We had such a lovely stay here. The kitchen is fully stocked with everything you might need and more, the sleeping arrangements were very comfortable, and the stars at night were breathtaking! We will definitely be back.

4.91 out of 5 average rating, 82 reviews

Home in Dover

FULLY renovated 1 bed/1 bath ski in-out condo!

AnastasiaRating, 5 stars2 months ago

My husband and I spent a long last winter weekend here. The condo was perfect for ski on/off and we enjoyed a day on the mountain. Though the weather wasn’t great the whole time, Brittany & Jen were quick to send recommendations for things to do, trails to hike and their favorite restaurants. So close to lots of great spots in this little mountain town. We would absolutely stay here again