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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Guest favorite
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
4.86 out of 5 average rating, 177 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
Cabin in Stratton
5 out of 5 average rating, 193 reviews

Log Cabin King Beds AC Near Hike Bike Swim Golf!

Kick back and relax in this calm, stylish, newly built log cabin which was finished in early 2022. Fully equipped with stainless steel appliances, soapstone counters, central a/c, all new furniture, mattresses and bedding. First floor master bedroom leads into a large, covered, screened in porch, which is perfect for your early morning coffee or evening cocktails. Starlink high speed Wi-Fi and a smart tv in the living room and bedroom. 7 Minutes from Stratton Mtn, 15 from Mt Snow. Nearby lakes!

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 374 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
Chalet in Winhall
4.98 out of 5 average rating, 129 reviews

Mountain view chalet with hot tub & fire pit!

Welcome to the @vermontviewchalet! This spacious, family-friendly property is perfect for year-round enjoyment. With the mountain view as your backdrop, come unplug by the fire pit and unwind in the hot tub. Perfectly situated between Manchester (shopping & dining) and Bromley/Stratton (skiing and entertainment). You're also just 2 minutes away from the Appalachian trail for the best hiking and fall foliage Southern Vermont has to offer. Look no further, you've arrived at your destination.

Top guest favorite
Cabin in Jamaica
4.99 out of 5 average rating, 302 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
Guesthouse in Jamaica
4.96 out of 5 average rating, 186 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
Cabin in Jamaica
4.95 out of 5 average rating, 103 reviews

The Woodland A-Frame

Welcome to The Woodland A-Frame! Built in 1965, our cozy cabin is located 20 mins from Stratton Mountain & Mt. Snow, and 30 mins from Bromley, & Magic Mountain! Vermont is a four-season state, allowing guests to enjoy the cabin anytime of year. Whether it's for fall foliage, winter activities, spring festivals, or a summer at the lake, we are happy to host you anytime during the year to experience your ideal Vermont getaway! Dogs welcome with a $100 pet fee per pet (two dog max). No cats

Guest favorite
The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.
Tiny home in Jamaica
4.94 out of 5 average rating, 1,351 reviews

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

Guest favorite
A cozy cabin is nestled in a snow-covered landscape, featuring a blue hammock hanging from the porch. Snowflakes gently fall around a dog wearing a blue coat, playing in the deep snow in front of the entrance. Wooden stools are positioned near the entrance.
Cottage in Jamaica
4.85 out of 5 average rating, 618 reviews

Cottage-Swim-View-Firepit-7min to Stratton-Dog OK

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
Chalet in Jamaica
4.98 out of 5 average rating, 286 reviews

Classic Vermont A-Frame | Fire Pit | Near Stratton

Escape to a classic Vermont A-Frame in Jamaica, Vermont on a private wooded 3-acre property along scenic Route 100. Near Stratton Mountain, Mount Snow, Jamaica State Park, and Pike Falls, this peaceful mountain retreat is perfect for hiking, swimming holes, fall foliage, scenic drives, and outdoor adventures. Enjoy mornings on the screened porch and evenings around the fire pit listening to the river across the street under the Vermont stars.

Guest favorite
A spacious hot tub is surrounded by natural stone paving and meticulously landscaped gardens. The tub has a waterfall feature and is enclosed by a retractable cover, creating an inviting space for relaxation outdoors.
Condo in Stratton
4.96 out of 5 average rating, 172 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 modern mid-century retreat is surrounded by snow-covered trees, with soft lighting emanating from floor-to-ceiling windows. The structure's sleek lines and wooden accents contrast with the winter landscape, inviting a sense of tranquility to the scene.
Home in Winhall
4.98 out of 5 average rating, 424 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.

Popular amenities for Stratton vacation rentals

When is the best time to visit Stratton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$135,954 GYDG$140,137 GYDG$103,953 GYDG$62,748 GYDG$56,473 GYDG$57,937 GYDG$58,565 GYDG$60,447 GYDG$56,264 GYDG$61,702 GYDG$73,206 GYDG$127,170 GYD
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Frequently Asked Questions

  • What types of vacation rentals are available in Stratton?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Stratton. From over 50 house rentals, over 50 condo rentals to over 10 cabin rentals, we've got you covered.

  • 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 house rentals in Stratton?

    Experience the best of Stratton with our house rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

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

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

  • Do house rentals in Stratton have wifi?

    Absolutely! We offer over 50 house rentals with wifi 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 30 house rentals with a bbq area in Stratton. Enjoy a tailored experience with all the comforts you desire.

  • Are there Stratton condo rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 condo rentals with pools in Stratton, available on Airbnb. Make a splash and soak up the sun in style!

  • 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.

  • Are there family-friendly house rentals in Stratton?

    Stratton has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about vacation rentals in Stratton

  • Total vacation rentals

    Explore 190 vacation rentals in Stratton

  • Nightly prices starting at

    Stratton vacation rentals start at G$14,641 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,810 verified reviews to help you choose

  • Family-friendly vacation rentals

    160 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    50 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

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  3. Vermont
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