Holiday rentals in Stratton

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Top-rated holiday rentals in Stratton

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
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, 161 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 favourite
Chalet in Stratton
4.99 out of 5 average rating, 179 reviews

7 Min Stratton Mtn/15 Min Mt Snow /Wood Fireplace!

Cozy chalet awaits your stay. This home sits on just under 4 acres. Sit back & enjoy the heated sunroom and stare out at the woods that surround you. You may be lucky enough to spot one of the moose or bear that visit the property. Kitchen remodeled 2023! Open floor plan w/wood burning fireplace. Main bedroom has new King Bed & twin bunks. Finished basement with new Queen size bed & twin bunk above. Kid friendly home! Mins to Stratton Mtn & Mt Snow for skiing & golf! Free Disc golf on property.

Top guest favourite
Guest house in North Bennington
4.99 out of 5 average rating, 309 reviews

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned space w/ cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. IG birchhousevt Please note that due to a severe allergy, it is difficult to accommodate animals

Top guest favourite
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, 275 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 favourite
Apartment in Stratton
4.97 out of 5 average rating, 190 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.

Superhost
A charming yellow house is nestled among snow-covered trees, framed by tall evergreens. A snow-blanketed driveway leads up to the entrance, inviting visitors into a serene winter retreat in a wooded setting.
Home in Stratton
4.83 out of 5 average rating, 111 reviews

Stay mins from Mt. Snow & Stratton w/ EV charger

Enjoy the ultimate ski getaway in this private home that sits on 1 acre of beautiful wooded land. Park your car in the detached garage (w/Tesla charger). The spacious house comfortably sleeps 8 guests and sits between Stratton Mountain and Mount Snow with hiking trails and lakes just minutes away. Sit outside on the deck to enjoy serene views, warm sunshine and sounds of nature. Leave your worries and just relax, BBQ and enjoy the fire pit for cozy evenings with friends & family.

Top guest favourite
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
4.98 out of 5 average rating, 131 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 favourite
A cozy living area features a mixture of seating options, including a tufted sofa and a vintage-style sofa adorned with decorative cushions. Natural wood floors enhance the warmth of the space, while artwork on the walls and a circular coffee table complete the inviting atmosphere.
Barn in Chester
4.99 out of 5 average rating, 710 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

Top guest favourite
The garden features raised vegetable beds surrounded by a wooden fence. In the background, the charming former church building with a pointed steeple is visible, framed by vibrant autumn foliage in shades of red and orange.
Guest suite in Brattleboro
4.95 out of 5 average rating, 609 reviews

Charming studio in renovated 19th century church.

This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

Top guest favourite
A spacious great room features a comfortable seating area with a white couch, eclectic armchair, and colorful floor design. Artistic decorations are placed on the walls and shelves, with a kitchenette visible in the background. A piano and drums are positioned nearby for guest use.
Guest suite in Wilmington
4.93 out of 5 average rating, 807 reviews

Architectural GuestSuite

The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

Top guest favourite
A mid-century retreat is illuminated at dusk, surrounded by snow-covered trees. Floor-to-ceiling windows create a warm glow, inviting guests into the living space. The landscape features a serene atmosphere with gently falling snow, enhancing the peaceful setting of the property.
Home in Winhall
4.98 out of 5 average rating, 406 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 favourite
Chalet in Winhall
4.97 out of 5 average rating, 127 reviews

Barrel Sauna + Hot Tub & Mtn Views

Escape to Stratton Chalet, 5 mins from a pristine swimming pond, featuring a new hot tub and barrel sauna with incredible Stratton mountain views. Recently renovated, Stratton Chalet features a large stone fireplace, outdoor, modern fire-pit area, two outdoor decks, contemporary outdoor furniture, Bose soundbar, and a well-equipped kitchen.

Popular amenities for Stratton holiday rentals

When is the best time to visit Stratton?

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Frequently Asked Questions

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

    Yes! Work meets play with ease at over 20 house 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 $100 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 house rentals in Stratton?

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

  • What are the most popular amenities for House Rentals in Stratton?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with wifi, over 20 homes with self check-in, over 20 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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.

  • 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 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.

  • Are there family-friendly house rentals in Stratton?

    Stratton has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • 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 Stratton townhouse rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 townhouse rentals with pools in Stratton, available on Airbnb. Make a splash and soak up the sun in style!

Quick stats about holiday rentals in Stratton

  • Total holiday rentals

    Explore 180 holiday rentals in Stratton

  • Nightly prices starting at

    Stratton holiday rentals start at € 59 per night before taxes and fees

  • Verified guest reviews

    Over 5,120 verified reviews to help you choose

  • Family-friendly holiday rentals

    150 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    180 of Stratton holiday rentals include wifi 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