Vacation rentals in Stratton

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Top-rated vacation rentals in Stratton

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Top guest favorite
The log cabin is illuminated against the night sky, showcasing its rustic charm. Snow accumulates around the entrance and pathway, while warm light spills from the windows, creating a cozy atmosphere. The sloped roof features wooden beams, enhancing the cabin's unique design.
Cabin in Stratton
5 out of 5 average rating, 182 reviews

Log Cabin, King Beds & 7 Min from Stratton Mtn

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!

Guest favorite
A contemporary A-frame house is set against a backdrop of lush greenery. Large windows dominate the facade, reflecting the evening sky. The outdoor seating area is visible, offering a welcoming space for relaxation amidst nature.
Cabin in Jamaica
4.88 out of 5 average rating, 327 reviews

Green Mountain Modern House: iconic modern getaway

Our unique, contemporary home is in the heart of the Green Mountain National Forest, all while offering all the perks of modern luxury in a secluded setting. Our amenities include open concept living and dining room, sauna, wood burning fireplace, front deck, backyard with fire pit and Adirondack chairs, and contemporary design and decor throughout. Now with EV charger, mini-split AC and heat, on-demand backup generator and high speed Starlink wifi (200+ mbs)! Pets welcome with a $100 pet fee.

Guest favorite
A modern interior is showcased with wooden walls and flooring, featuring a cozy bed positioned near large windows. A compact dining area is visible, with a small table and two chairs. An air conditioning unit is installed on the wall, contributing to the space's comfort.
Home in Winhall
4.94 out of 5 average rating, 323 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Top guest favorite
The entrance of the Bonnet St Barn features a deep red exterior with a sloping roof and an overhang. A small chair is positioned beside the door, framed by lush greenery and blooming flowers, enhancing the welcoming entryway.
Apartment in Manchester
4.99 out of 5 average rating, 109 reviews

Bonnet St Barn

Keep it simple at the peaceful, cozy and centrally-located Bonnet St Barn. Conveniently located steps from Manchester’s landmark 'Northshire Bookstore', restaurants and delightful shopping. The apartment is on the main floor of the two-story barn and features a king-size bed, a smaller second bedroom with a twin bed, AC, high speed WiFi, TV and a full kitchen for relaxing mealtimes. Less than 30-minute drive to Bromley & Stratton ski areas. Enjoy the Green Mountains of southern Vermont!

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, 294 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
The rustic barn structure features a combination of dark wood siding and a gabled roof, highlighted by a central chimney. Large wooden doors and multiple small windows create an inviting appearance, while the surrounding natural landscape includes lush trees and open fields.
Barn in Jamaica
4.97 out of 5 average rating, 113 reviews

The Rafters Lodge

A unique VT experience! This 1860s barn was converted into a Girl Scout camp in the 1950s and served many years training leaders and scouts. Today, the Rafters continues to be a special part of many families lives, who come to enjoy the rustic camping experience and beautiful ninety acre farm. The lodge has accommodated large youth groups, families and even the occasional wedding party. With the close proximity to Stratton and Bromley, visitors enjoy countless recreational opportunities.

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, 1,331 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
A cozy living area features a large sectional sofa adorned with decorative cushions. A wooden coffee table sits in the center, surrounded by an area rug. A stone fireplace with a fire is visible, enhancing the space's comfort, and a staircase leads to the upper level.
Home in Winhall
4.97 out of 5 average rating, 149 reviews

3BR 2BA Stratton Condo w/ Fireplace & Forest Views

Newley renovated 3 bed 2 full bath condo on Stratton, just minutes to Stratton's base lodge. Kitchen is well equipped for cooking. Private balcony with forest views. All new appliances. Wood burning fireplace & firewood included. All beds & baths are on 2nd floor up spiral staircase which may be difficult for elderly or young children. Stairs are required. Master bed has en suite full bath and smart tv. Free parking. Living room has an 86" smart TV. Poker set, & board games.

Top guest favorite
The cabin features a wooden exterior surrounded by lush greenery, with large windows allowing natural light to enter. A wooden deck extends from the side, leading to a cozy outdoor area and an adjacent structure, contributing to the rustic charm of the setting.
Tiny home in Dover
5 out of 5 average rating, 211 reviews

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, water, coffee, tea, milk, fresh eggs + homemade soap. It has an indoor compost toilet, outhouse + outdoor shower (May-Oct) Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

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, 602 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
4.96 out of 5 average rating, 165 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.

Guest favorite
Loft in Jamaica
4.93 out of 5 average rating, 112 reviews

Rustic Stratton Area Studio near Pikes Falls

Stratton Mountain Convenience - Cozy fully renovated studio apartment on 10 acre property conveniently located less than 5 minutes to all that Stratton Mountain Resort has to offer. Walking distance to Pikes Falls. Unit is most suitable for 2 people. We highly recommend guests have all wheel drive vehicles during the winter months.

Popular amenities for Stratton vacation rentals

When is the best time to visit Stratton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR10,838 ZARR11,007 ZARR9,635 ZARR5,080 ZARR4,572 ZARR4,691 ZARR4,742 ZARR4,894 ZARR4,555 ZARR4,996 ZARR5,927 ZARR10,296 ZAR
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 60 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 $190 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 20 house rentals with a bbq area in Stratton. Enjoy a tailored experience with all the comforts you desire.

  • Are there Stratton house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 house 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 R1,185 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 5,120 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

    60 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    190 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
  4. Windham County
  5. Stratton