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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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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
4.85 out of 5 average rating, 159 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, 182 reviews

Log Cabin, King Beds & AC Near Hike/Swim/Golf/Bike

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
A warm living space is highlighted by a stone fireplace, wooden walls, and large windows that frame the surrounding trees. The area features a cozy couch with a throw blanket, a rustic dining table, and multiple black dining chairs, creating an inviting atmosphere.
Home in Wardsboro
4.96 out of 5 average rating, 117 reviews

Hot Tub & Game Room - Ski Mt. Snow/Stratton

Nestled in the heart of Southern Vermont, our cozy and inviting home sits 10 min from Mt Snow and 15 min from Stratton, making it the ideal base for your adventure. Whether you're hitting the slopes, exploring hiking trails, or simply unwinding, you'll find everything you need for a memorable stay. Soak under the stars in our 7-person hot tub or cozy up inside for a night of relaxation. Discover the charm of Vermont and visit local breweries, farm-to-table restaurants, farms, and quaint towns.

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 332 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, 272 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.

Guest favorite
Condo in Stratton
4.97 out of 5 average rating, 185 reviews

Premier Stratton Village Location - Pool & Hot Tub

-- Walk across the street to Stratton Ski Lifts -- Conveniently located near the Stratton Village, this condo places you at the center of all the mountain activities - skiing, mountain biking, events, weddings, shopping & dining. This updated studio includes gas fireplace, AC, stainless appliances, and nice décor. Long Trail House condos boasts underground heated parking, year-round outdoor pool with patio and multiple hot tubs, and sauna. Come visit and relax in the Vermont mountains.

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, 1,306 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 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, 152 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
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, 726 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This 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.

Superhost
An open living area features a large wooden dining table surrounded by metal chairs. The kitchen showcases modern appliances and a sleek countertop, while a comfortable seating area is arranged nearby with a sectional couch and coffee table against a textured wall.
Condo in Stratton
4.96 out of 5 average rating, 104 reviews

Luxury Stratton condo just steps to the lift!

Enjoy this beautifully renovated 1 bed/1 bath condo with a live fireplace conveniently located steps from the mountain and Stratton Village! The Tamarack chair lift is only a few hundred yards away! Washer and dryer in unit to warm up your wet clothes after a long day of skiing or mountain biking. Fully stocked kitchen, 50’ TV w/ AppleTV, cable, Amazon Alexa, 5G WiFi, Firewood and more! This is one of the nicest Ober Tal condos available for rent!

Superhost
A modern cabin features a contrasting black exterior and wooden accents, nestled among lush trees. A wide deck with railing leads to the entrance, offering a welcoming space to enjoy the surrounding nature. Large windows provide ample natural light and views of the forest.
Tiny home in Athens
4.9 out of 5 average rating, 152 reviews

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

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, 154 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.

Popular amenities for Stratton vacation rentals

When is the best time to visit Stratton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$592,194 CLP$601,447 CLP$526,497 CLP$277,591 CLP$249,832 CLP$256,309 CLP$259,085 CLP$267,412 CLP$248,906 CLP$267,412 CLP$276,665 CLP$528,348 CLP
Avg. temp23°F25°F33°F46°F56°F64°F69°F67°F60°F49°F39°F29°F

Frequently Asked Questions

  • Are there pet-friendly house rentals in Stratton?

    Four-legged friends are welcome in Stratton. Choose from more than 10 house rentals for guests traveling with pets.

  • 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 family-friendly townhouse rentals in Stratton?

    Stratton has more than 20 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • 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.

  • 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.

  • 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.

  • Do cabin rentals in Stratton have a bbq area?

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

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

    Yes! Work meets play with ease at over 10 townhouse 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 $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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 $64,771 CLP 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