Holiday houses in Wardsboro

4.85 out of 5 average rating, 134 reviews

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

4.95 out of 5 average rating, 111 reviews

Hot Tub & Game Room - Ski Mt. Snow/Stratton

Nestled in the heart of Southern Vermont, our cozy and inviting home sits 10 min from Mt Snow and 15 min from Stratton, making it the ideal base for your adventure. Whether you're hitting the slopes, exploring hiking trails, or simply unwinding, you'll find everything you need for a memorable stay. Soak under the stars in our 7-person hot tub or cozy up inside for a night of relaxation. Discover the charm of Vermont and visit local breweries, farm-to-table restaurants, farms, and quaint towns.

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

Guesthouse 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.

Superhost

Cottage in Putney

4.82 out of 5 average rating, 271 reviews

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.

4.94 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

4.95 out of 5 average rating, 135 reviews

Cabin w/Hot tub, Sauna near Mt.Snow & Stratton.

Rustic cabin situated on a quiet cul-de-sac between Mt. Snow & Stratton Mtns. Features 2 beautiful wood burning fireplaces, sauna, outdoor hot tub & fire pit and Generac stand by generator. Modern kitchen on main floor w/4 bedrooms and 2 full bathrooms . Huge open concept layout perfect for entertaining. Natural light beams in onto the loft and master bedroom just upstairs from the main floor. Basement offers a pull out couch w/ easy access from driveway. Coffee /Firewood included.

4.83 out of 5 average rating, 526 reviews

Cottage in Jamaica

Cottage 7min to Ski Stratton-WoodStove,Views,DogOK

Authentic post & beam cottage surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Nearby swimming hole at brook on property. Fire pit, propane BBQ, picnic table, spectacular Stratton Mountain view. Front porch & back porch with hammock, table & chairs. VCR/DVD & videos, boardgames & puzzles, kids toys, turntable & records, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Gas heat, wood stove. Dog friendly.

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.

4.98 out of 5 average rating, 259 reviews

Chalet in Jamaica

Vermont Chalet

This is a place for those who are looking to enjoy a peaceful mountain escape with modern conveniences and who love the outdoors. This private wooded 3-acre Southern Vermont property is directly across the street from the Green Mountain National Forest and nearby a wide variety of outdoor destinations. Our pictures and guest reviews say it all :)

4.93 out of 5 average rating, 189 reviews

Cabin in Jamaica

Romantic Wooded Vermont Cabin

Enjoy this private getaway for two in our charming and rustic home nestled on a peaceful, wooded lot at the edge of a national forest. First floor only, open floor plan and it's all yours! Conveniently located 2 miles from Jamaica Village, 10 miles from Stratton Mountain, 16 miles from Manchester and 30 miles north of Brattleboro.

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Other great holiday rentals in Wardsboro

5 out of 5 average rating, 58 reviews

Hot Tub, Game Room, Minutes to Mt. Snow & Stratton

ChloeRating, 5 stars2 months ago

Whitley's place was just what we were looking for for our family weekend! Plenty of space with lots to do, the pool table was a big hit. Very close to Mount Snow and Stratton which was really convenient for the snowboarders/skiers in our group. Had a great time and would love to be back!

5 out of 5 average rating, 12 reviews

MtSnow/Stratton Ski Lodge-Hot Tub-Game Room-Pool

ChrisRating, 5 stars2 months ago

This home is Stunning!!! In every aspect! Every room is beautiful and Michelle has thought of every detail to make you feel at home. Incredibly comfortable beds and linens, a fully stocked kitchen for all your cooking/takeout desires, and hang out spot for the kids with air hockey and arcade basketball! I could go on and on. You will not want to leave!

5 out of 5 average rating, 15 reviews

Mountain house w/ large hot tub

PaulaRating, 5 stars2 months ago

We thoroughly enjoyed our stay at this beautiful home. It was equipped with everything we needed and more. The house was clean and spacious. Zach was very responsive via messages to our needs. We would definitely stay here again for our family ski trip to Stratton.

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!

Superhost

Home in Dover

4.91 out of 5 average rating, 82 reviews

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

4.95 out of 5 average rating, 85 reviews

Cozy Ski Cabin with Hot Tub, Fireplace, EV Frndly

JeffRating, 5 stars2 weeks ago

Great Cabin to have some friends or family with and to get away from surburbia. Enjoyable hot tub, outdoor and indoor fire pit and a deck to be with all guests. Adequate sleep set-up for familys. Would stay here again!

4.98 out of 5 average rating, 65 reviews

Log Cabin near Mt Snow & Stratton w/ Fire Pit

TanujRating, 5 stars2 weeks ago

We had such a great stay at the House of David over Memorial Day weekend. The house is tucked away among beautiful mountains and rivers, and honestly, it felt just like staying in a cozy cabin inside a national park—but with all the modern comforts you’d want. Everything was spotless and welcoming, so we felt right at home as soon as we arrived. The inside has a really nice vibe, with lots of natural touches that make you feel connected to the outdoors, but you still have all the amenities you need. The basement game room was a big hit with both the adults and the kids. The screened porch was another favorite spot; it was so nice to relax outside without worrying about mosquitos. Since the house is on a private road, it was really peaceful and we didn’t have to worry about cars, which was great for the kids. The beds were super comfortable, the kitchen had everything we needed, and the whole place was just immaculately clean. We made wonderful memories here and would love to be back!