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 R 1,175 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 5,900 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
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford
4.95 out of 5 average rating, 146 reviews

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

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, 185 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
5.0 out of 5 average rating, 198 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, 391 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 chalet is set against a backdrop of trees, showcasing a combination of natural stone and wood siding. Multiple outdoor seating areas are visible, featuring colorful chairs with a fire pit nearby. Dim evening light gently illuminates the home, highlighting the windows and inviting ambiance.
Chalet in Jamaica
4.99 out of 5 average rating, 106 reviews

Designer Chalet w/ Mountain Views close to it all

A perfect little getaway. This stylish 3 bedroom/2 bath chalet is surrounded by endless outdoor activities. Swimming, hiking, biking, visiting the local waterfalls, golf courses, or rent an ATV from local outfit. This beautiful home is perfect for 6-8 people. Situated on 2.5 acres, this private setting with mountain views, has everything you need to feel at home. Multiple restaurants, cafes, markets for food, beer & wine less than a 5 min drive as well to sporting stores for supplies.

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, 1369 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, 315 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
Tiny home in Ludlow
4.96 out of 5 average rating, 103 reviews

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

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, 628 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, 291 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, 176 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, 429 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. priceR 10,908 ZARR 11,243 ZARR 8,340 ZARR 5,034 ZARR 4,531 ZARR 4,648 ZARR 4,699 ZARR 4,850 ZARR 4,514 ZARR 4,950 ZARR 5,873 ZARR 10,203 ZAR
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

Frequently Asked Questions

  • What are the best places to stay in Stratton?

    Stratton has cozy village cabins, mountain lodges, and family-friendly vacation rentals nestled near popular outdoor activities. Staying around Stratton Village gives easy access to dining, shops, and trails.

  • What are the best things to do in Stratton with kids?

    Families explore seasonal mountain adventures like skiing or snowboarding, discover nature along local hiking trails, and enjoy village fun with shops, games, and casual eateries. Stratton Mountain Resort frequently suggests activities suitable for all ages.

  • What are some of the best things to do in Stratton?

    Stratton has outdoor experiences like skiing, snowshoeing, and hiking along scenic trails. Visitors often explore Stratton Village's shops and sample local Vermont flavors at nearby restaurants.

  • How is the weather in Stratton?

    Winters in Stratton are cold, ranging from 13–32°F (-11–0°C), with snow great for winter sports. Summers bring milder afternoons near 57–81°F (14–27°C), often suggested for hiking and outdoor festivals.

  • When is the best time to visit Stratton?

    Many visitors prefer the vibrant summer and fall seasons for hiking, village events, and mountain views. Winter draws snow sport enthusiasts, with ski slopes and cozy après-ski experiences.

  • What are the best places to visit in Stratton?

    Stratton Mountain Resort is frequently suggested for skiing and summer adventure activities. Stratton Village has local boutiques, art galleries, and dining reflecting the area's mountain character.

  • What are some hiking trails in Stratton?

    Explore trails around Stratton Mountain, such as the paths leading toward the summit or through forested areas. The Appalachian Trail crosses nearby, inviting hiking enthusiasts to discover Vermont’s landscape.

  • What are some family activities we can do in Stratton?

    Families enjoy mountain activities like skiing, snowboarding, hiking, and village exploration. Many opt for bike rentals or adventure centers that feature ziplining and climbing walls around Stratton Mountain Resort.

  • What are some of the best day trip ideas from Stratton?

    Explore neighboring Vermont villages for artisan shops, scenic drives, or historic sites. Outdoor parks and nature preserves around southern Vermont provide opportunities for hiking, biking, and wildlife watching.

  • Are there any pet friendly accommodations available in Stratton?

    Stratton has pet-friendly vacation rentals and cabins, especially in and around Stratton Village. Many outdoor trails welcome leashed pets, making it convenient to enjoy mountain adventures with your dog.

  • What are some local tips for visiting Stratton?

    Dress in layers for mountain weather changes and bring sturdy footwear for hiking. Locals often pack reusable water bottles and check for seasonal village events or markets for unique finds.

  • What is Stratton known for?

    Stratton is known for its mountain resort with prominent skiing and snowboarding terrain, along with hiking trails and vibrant summer festivals. The village area features locally sourced dining and artisan shopping.

  • What are the best hidden gems to explore in Stratton?

    Stratton has peaceful forest trails, independent galleries, and locally owned shops tucked away around the village. Visitors often seek out scenic viewpoints from less-traveled paths near the mountain.

  • What are the best foods to try in Stratton?

    Locally rooted foods include Vermont cheddar, maple syrup-infused dishes, and comfort fare at mountain cafés. Artisanal bakeries and farm-inspired menus are frequently suggested for a taste of regional flavors.

  • What should I bring for a trip to Stratton?

    Pack weather-appropriate layers, sturdy shoes, and gear for mountain activities like skiing or hiking. A reusable water bottle, snacks, and sun protection are practical for enjoying the outdoors year-round.

  • What is the nightlife in Stratton like?

    Stratton Village has a mix of casual pubs, après-ski spots, and live music venues. Evening gatherings often center around mountain lounges and friendly taverns.

  • What are the most popular events or festivals in Stratton?

    Stratton hosts recurring music and arts festivals, seasonal mountain sport competitions, and village gatherings during summer and around Labor Day weekend. Winter often brings festive celebrations linked to ski season.

  • Are there family friendly vacation rentals in Stratton?

    Many vacation rentals in and near Stratton Village are sized for families, with convenient access to mountain activities and village amenities. Larger cabins and condos often include kitchens and space for group gatherings.

Destinations to explore

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