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Vacation rentals in Stratton

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Top-rated vacation rentals in Stratton

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

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Top guest favorite
The rustic cabin features a red exterior with a metal roof, framed by lush greenery. Flower pots with colorful blooms adorn the porch, which includes a small table and chairs. Large windows allow natural light to illuminate the interior.
Cabin in Londonderry
4.94 out of 5 average rating, 366 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Superhost
The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.
Cabin in Wardsboro
4.85 out of 5 average rating, 155 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.

Top guest favorite
Chalet in Stratton
4.99 out of 5 average rating, 174 reviews

Family Chalet Mins from Stratton Mtn/Hikes/Biking

Cozy chalet awaits your stay. This home sits on just under 4 acres. Sit back and enjoy the heated sunroom and stare out at the woods that surround you. You may be lucky enough to spot one of the moose or bear that visit the property. Kitchen remodeled June 2023! Open floor plan w/wood burning fireplace. Main bedroom has Qn bed & twin bunks. Finished basement with new Qn size bed and twin bunk above. Kid friendly home! Mins to Stratton Mtn & Mt Snow for skiing & golf! Free Disc golf on property!

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 312 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favorite
The cabin's exterior showcases a warm wooden facade with large, strategically placed windows. A spacious screened porch extends from the building, inviting natural light and outdoor enjoyment. A stone pathway leads to the entrance, surrounded by landscaped gravel and native vegetation.
Cabin in Jamaica
4.99 out of 5 average rating, 265 reviews

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.

Top guest favorite
A spacious bedroom features a king-sized bed adorned with colorful pillows, framed by large windows that offer views of the surrounding greenery. A decorative bench at the foot of the bed displays neatly arranged towels, complemented by bedside lamps on either side.
Guesthouse in Jamaica
4.96 out of 5 average rating, 179 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.

Guest favorite
An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.
Cottage in Shaftsbury
4.98 out of 5 average rating, 718 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

Guest favorite
The exterior of Hygge House is highlighted by sleek wooden siding and a modern design. Large windows reflect the surrounding greenery, while a stone pathway leads to the entrance. Sunlight filters through the trees, illuminating the inviting facade set on a spacious grassy area.
Chalet in Stratton
4.96 out of 5 average rating, 148 reviews

Luxe HOT TUB, SAUNA 8–12 min Stratton & Mount Snow

Welcome to HYGGE HOUSE, a luxurious modern retreat on 4 wooded acres in Stratton. Inspired by the Danish concept of hygge, this home embodies warmth, coziness, and well-being. Unwind year-round in a private HOT TUB, SAUNA, and even a TREEHOUSE for the ultimate mountain getaway. Just minutes from Stratton and Mount Snow resorts, this architectural gem is a haven for relaxation and adventure, with an open floor plan, cozy fireplace, and large windows connecting you to nature.

Guest favorite
A charming cottage entrance is depicted with natural wood siding and a small porch area. Soft lighting enhances the ambiance. A friendly dog sits on the gravel path, surrounded by lush greenery, indicating a tranquil forest setting.
Cottage in Jamaica
4.84 out of 5 average rating, 565 reviews

Cottage-7 min to Ski Stratton-Woodstove-View-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.

Guest favorite
A cozy living area features a pair of brown sofas with decorative cushions. A wooden coffee table is centered in front of the seating. Artwork is displayed on the light green walls, and a lamp provides soft illumination, complementing the natural light from the window.
Condo in Stratton
4.95 out of 5 average rating, 152 reviews

Cozy condo within walking distance to the slopes.

Cozy condo within walking distance of the slopes and restaurants and shops at Stratton Mountain Village. After a day on the slopes relax in the hot tub or take a dip in the heated pool or maybe enjoy some time in the sauna. Then enjoy sitting in front of the gas fireplace and maybe watch a movie. TV is a smart TV, basic cable is included - personal password needed for Netflix, Hulu, etc.

Top guest favorite
A spacious living area features large floor-to-ceiling windows offering a view of the green outdoor space. A plush sofa, accented with colorful cushions, sits in front of a wooden coffee table. A modern dining area is visible in the background, illuminated by soft lighting.
Home in Winhall
4.98 out of 5 average rating, 403 reviews

Stunning mid-century house on 2.5 private acres

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.

Superhost
Cabin in Jamaica
4.92 out of 5 average rating, 197 reviews

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.

Popular amenities for Stratton vacation rentals

Frequently Asked Questions

  • Do condo rentals in Stratton have a gym?

    Absolutely! We offer over 10 condo rentals with a gym in Stratton. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Stratton have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Stratton. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Stratton have wifi?

    Absolutely! We offer over 20 apartment rentals with wifi in Stratton. Enjoy a tailored experience with all the comforts you desire.

  • Are there Stratton vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 50 vacation homes with pools in Stratton, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there vacation rentals with a dedicated workspace in Stratton?

    Yes! Work meets play with ease at over 80 vacation rentals in Stratton featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in condo rentals in Stratton?

    Experience the best of Stratton with our condo rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly vacation rentals in Stratton?

    Stratton has more than 150 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Cabin Rentals in Stratton?

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a bbq area, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do cabin rentals in Stratton have self check-in?

    Absolutely! We offer over 10 cabin rentals with self check-in in Stratton. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Stratton?

    Four-legged friends are welcome in Stratton. Choose from more than 40 vacation rentals for guests traveling with pets.

Quick stats about vacation rentals in Stratton

  • Total vacation rentals

    Explore 180 vacation rentals in Stratton

  • Nightly prices starting at

    Stratton vacation rentals start at $70 per night before taxes and fees

  • Verified guest reviews

    Over 5,120 verified reviews to help you choose

  • Family-friendly vacation rentals

    150 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    180 of Stratton vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Stratton rentals

  • 4.9 Average rating

    Stratton stays are highly rated by guests—averaging 4.9 out of 5!

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Stratton