Vacation rentals in Stratton

4.94 out of 5 average rating, 349 reviews

The rustic cabin features a red exterior with a metal roof, framed by lush greenery. Flower pots with colorful blooms adorn the porch, which includes a small table and chairs. Large windows allow natural light to illuminate the interior.

Cabin in Londonderry

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Superhost

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

4.84 out of 5 average rating, 148 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.

A newly built log cabin displays charming wooden siding and a stylish metal roof, surrounded by lush greenery. A small porch with steps leads to the entrance, while a gravel area provides access to the cabin. The sky above is clear with a few clouds.

5 out of 5 average rating, 162 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!

Guesthouse in North Bennington

The entrance to the guest house displays a dark wood-paneled exterior with a black door featuring a grid window. A small window is positioned beside the door. Recessed lighting illuminates the covered porch area above.

4.99 out of 5 average rating, 274 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

4.94 out of 5 average rating, 120 reviews

A cozy log cabin is nestled among tall trees, with sunlight filtering through the leaves. The surrounding ground is covered in vibrant autumn leaves, and a winding path leads to the front entrance of the home, offering a serene and inviting atmosphere.

Chalet in Londonderry

10 min from Stratton! Log Cabin w/ Beautiful Views

Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!

4.99 out of 5 average rating, 255 reviews

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

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.

4.95 out of 5 average rating, 166 reviews

A spacious bedroom features a king-sized bed adorned with colorful pillows, framed by large windows that offer views of the surrounding greenery. A decorative bench at the foot of the bed displays neatly arranged towels, complemented by bedside lamps on either side.

Guesthouse in Jamaica

The Chick Inn

This is a two-story, renovated barn adjacent to the chicken coop in rural Vermont with views of the forests. It has brand new floors, a new kitchenette, and fresh look. (Some renovation is still taking place.) The chicken coop is just next door but the birds are free-range and range they will. Enjoy a private, hot shower in the garden, just outside. This listing is only suitable for people comfortable with dogs, cats, and chickens which will undoubtedly greet you outside during your stay.

4.94 out of 5 average rating, 174 reviews

A cozy dining area is highlighted by a round wooden table surrounded by black chairs. The open living room features a comfortable sofa and a decorative area rug. Soft lighting is provided by a stylish chandelier, enhancing the homey atmosphere.

Condo in Stratton

Updated Ski in/Ski out Stratton Condo!

Enjoy our cozy ski-in ski -out condo in the Ober Tal complex at Stratton. This newly renovated condo offers a warm, welcoming stay with modern farm house charm! Located just above the base of the mountain, our condo is a stones throw from the nearest lift ( 200 ft) and a ski lovers dream. Unwind after a long day of skiing/snowboarding or take convenient 5 minute stroll to the Village for a bite to eat or some shopping. *Mountain biking & concerts offered in the summer season.*

Guest suite in Brattleboro

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.

4.94 out of 5 average rating, 592 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.

4.89 out of 5 average rating, 106 reviews

The exterior of the chalet is shown, featuring a classic A-Frame design. Large windows invite natural light, reflecting the surrounding greenery. A wooden door leads to the entrance, and a spacious deck extends outward, surrounded by trees, offering a sense of seclusion.

Chalet in Jamaica

Classic A-Frame in Jamaica

This classic A-Frame chalet awaits you and your friends and family, whether you enjoy skiing/snowboarding, hiking, kayaking or just reading in front of a fire. With 2 bedrooms and a loft, galley kitchen and open living area, you can relax and enjoy all that Southern Vermont has to offer. Centrally located to Stratton, Mount Snow, Magic and Bromley ski resorts.

The cabin is illuminated by warm lights against a serene winter backdrop. A spacious deck extends from the structure, surrounded by snow and trees. The inviting glow from the windows enhances the cozy ambiance of the retreat.

4.97 out of 5 average rating, 191 reviews

Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi

- Secluded forest cabin with a babbling brook for a peaceful escape - Relax in the private hot tub under the stars or cozy up by the fire pit - High-speed WiFi, dedicated workspaces, and a kid-friendly play area - Just 9 min to Stratton Mountain Resort and 14 min to Mount Snow - Book now and enjoy a tranquil retreat with all the comforts of home

4.98 out of 5 average rating, 264 reviews

The exterior of the A-frame is showcased, featuring a triangular roof and three distinct yellow doors. The porch offers a space to relax, while a stacked bundle of firewood is neatly arranged below, surrounded by lush green foliage and the natural beauty of the forest.

Chalet in Jamaica

Vermont Chalet

This is a place for those who are looking to enjoy a peaceful mountain escape with modern conveniences and who love the outdoors. This private wooded 3-acre Southern Vermont property borders Green Mountain National Forest (not a main entrance) and nearby a wide variety of outdoor destinations. Our pictures and guest reviews say it all :)

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Stay near Stratton's top sights

Stratton Mountain158 locals recommend

Stratton Mountain Resort65 locals recommend

Stratton Mountain Golf Course14 locals recommend

Other great vacation rentals in Stratton

5 out of 5 average rating, 29 reviews

The living area features a spacious sofa and armchair, framed by large windows that provide ample natural light. Exposed wooden beams run along the ceiling. A decorative rug adds color to the hardwood floor, and a mantelpiece serves as a focal point in the room.

Home in Tinmouth

Charming Vermont Schoolhouse

4.94 out of 5 average rating, 50 reviews

The kitchen features warm wood cabinetry and a countertop with bar seating for two. A stainless steel stove and microwave are included, with utensils hanging above the sink. The mosaic tile backsplash adds texture, while natural light filters in through the window.

Apartment in Dover

Cozy Brookside Getaway

5 out of 5 average rating, 57 reviews

The exterior of a two-story house is depicted, featuring a welcoming entrance with wooden steps and a green door. Window boxes with plants are positioned below each window on the light gray facade, surrounded by a landscaped yard with a gravel pathway leading to the front door.

Apartment in Londonderry

Bread and Butter Apartment

Superhost

The living area features a stone fireplace with a wood-burning fire, surrounded by wooden walls. Two small windows allow natural light, while wooden beams are visible on the ceiling. A rustic table sits in front of the fireplace, complemented by a rocking chair and a red armchair.

4.86 out of 5 average rating, 22 reviews

Adorable 2 bedroom Cabin with a romantic fireplace

5 out of 5 average rating, 55 reviews

An open living area features vaulted ceilings and large windows, allowing natural light to fill the space. A comfortable leather sofa sits adjacent to a dining table, with views of the surrounding greenery visible outside. A spacious kitchen island adds functionality to the layout.

Home in East Dover

Magical Retreat Cottage - Waterfalls everywhere

4.91 out of 5 average rating, 74 reviews

A two-story condo is shown with a snow-covered roof and a well-maintained exterior. A vehicle is parked in front, and snow blankets the surrounding area. The backdrop features a snow-covered mountain, displaying ski trails that contour the slopes.

Condo in Stratton

Stratton Mountain vacation spot

5 out of 5 average rating, 15 reviews

A bright and spacious living area is presented, featuring a comfortable gray sofa set against wooden flooring. A work-from-home station is positioned by large windows overlooking the outdoors. Natural light floods the room, complemented by ceiling fans and light-colored walls.

Home in Stratton

Beautiful 3-4 BR, 2 Ba, Sleeps 9

A modern kitchen features dark cabinetry and stainless steel appliances, including a gas stove and refrigerator. A light-colored countertop complements the white tile backsplash. A vibrant red checkered mat is placed in front of the sink, adding a touch of color to the space.