Vacation rentals in Stratton

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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$14,619 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!

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
4.87 out of 5 average rating, 180 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.

Guest favorite
Yurt in Dover
4.91 out of 5 average rating, 112 reviews

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Mount Snow Yurt is a one-of-a-kind luxury getaway nestled in the tranquil serenity of Vermont’s mountains, just 7 minutes from the Mount Snow Ski Resort, an Epic Pass destination. This magnificent pet-friendly yurt is surrounded by the captivating scenery of Mount Snow and is located near a beautiful creek, providing an even more peaceful and serene atmosphere. Furnished with modern amenities, including a luxurious private sauna, this yurt offers everything you need for a relaxing stay in nature

Top guest favorite
Cabin in Stratton
5 out of 5 average rating, 195 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, 382 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 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, 1,360 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

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, 307 reviews

Cozy Cabin at Frog Pond Farm

Cozy 500sq ft passive solar cabin on our small farm, 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/gardens or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Top guest favorite
A cozy living area features wooden paneling and a warm brown sofa, complemented by a natural wood coffee table on a cowhide rug. A vibrant wall displays green foliage and the phrase 'Green Mountain State.' Four bar stools are positioned nearby, offering additional seating.
Chalet in Wardsboro
5 out of 5 average rating, 100 reviews

Brook Haven Retreat - Minutes to Mt Snow&Stratton

Welcome to Brook Haven Retreat! We are situated directly on Wardsboro Brook, just minutes away from the best skiing and riding, hiking, biking, fishing and relaxation in Southern Vermont.The property features a private fenced yard and deck to take in all the beauty alongside the brook. The home is fully updated with modern conveniences including three sleeping areas, living room, and a fully stocked kitchen. We love and allow well-behaved furry friends in our home!

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
4.85 out of 5 average rating, 624 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.

Top guest favorite
Chalet in Jamaica
4.98 out of 5 average rating, 287 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 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
4.96 out of 5 average rating, 174 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, 426 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.

Top guest favorite
A modern cabin is set amidst lush greenery, elevated on stilts for an unobstructed view. The exterior features a mix of wood and dark finishes, with large windows allowing natural light to fill the interior. A gravel path leads to the entrance.
Home in Jamaica
4.94 out of 5 average rating, 129 reviews

The Post Haus: one-of-a-kind modern VT experience

Welcome to The Post Haus! A one-of-a kind, modern Vermont mini cabin in the Green Mountain National Forest. This high-end, mid-century mod getaway offers an indoor wood-burning fireplace, sauna, high-end kitchen, and two acres alongside the beautiful Ball Mountain Brook. Come enjoy our truly special piece of Vermont!

Popular amenities for Stratton vacation rentals

When is the best time to visit Stratton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$135,747 GYDG$139,924 GYDG$103,794 GYDG$62,653 GYDG$56,387 GYDG$57,849 GYDG$58,476 GYDG$60,355 GYDG$56,178 GYDG$61,608 GYDG$73,095 GYDG$126,976 GYD
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

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.

Destinations to explore

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