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Vacation rentals in Stratton

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Stratton vacation rentals

Self check-in
Gym
BBQ grill
Laptop-friendly workspace
Wifi

Stay near Stratton's top sights

Stratton Mountain406 locals recommend
Stratton Mountain Resort239 locals recommend
Stratton Mountain Golf Course43 locals recommend

Stratton house rentals

Top guest favorite
A white farmhouse-style structure is set on a lush green hill, surrounded by a clear blue sky. The building features a gabled roof, multiple windows, and a small cupola. A neat lawn frames the house, emphasizing its inviting exterior.
Home in Bennington
4.98 out of 5 average rating, 307 reviews

Cozy Modern Sugar House with spectacular views.

Guest favorite
An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.
Home in Londonderry
4.99 out of 5 average rating, 143 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

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, 114 reviews

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

Guest favorite
A cozy fire pit is surrounded by stone, situated in the foreground of a spacious lawn. In the background, a modern chalet features large windows and a combination of wood and stone siding, framed by colorful autumn foliage.
Home in Winhall
4.95 out of 5 average rating, 152 reviews

Summit View Ski and Golf Retreat w/hot tub & Sauna

Top guest favorite
The colonial home features a classic two-story facade with symmetrical windows and a central chimney. Lush green landscaping surrounds the entrance, which is accentuated by a welcoming front porch. Fall foliage decorates the yard, providing a colorful backdrop to the property.
Home in Sandgate
4.99 out of 5 average rating, 119 reviews

Country Colonial Home with rolling fields & stream

Superhost
The image captures a view from a wooden deck illuminated by string lights. A cozy seating area features an Adirondack chair and a gas fire pit, with the West River flowing nearby, reflecting the soft light of dusk.
Home in Jamaica
4.93 out of 5 average rating, 181 reviews

Cozy Riverfront Home in beautiful Jamaica

Guest favorite
An organically shaped mini-house is surrounded by lush greenery, with a stone pathway leading to a softly lit entrance. The structure features unique, curvaceous walls and several windows, harmoniously blending with the natural landscape of trees and foliage.
Home in Pownal
4.97 out of 5 average rating, 264 reviews

Cozy Vermont mini-house

Superhost
Home in Jamaica
4.86 out of 5 average rating, 297 reviews

Yellow Sweetie at the Base of Stratton

Stratton condominium rentals

Guest favorite
A living room features a large stone fireplace with a wood storage basket beside it. A comfortable sofa with decorative pillows faces a wooden coffee table. Natural light floods the space through a large window, complemented by a nearby area rug.
Condo in Dover
4.87 out of 5 average rating, 242 reviews

Mt Snow Ski In/Out at Seasons

Top guest favorite
A spacious living area features a large sectional sofa adorned with cozy throw pillows, complemented by a textured area rug. Natural light pours in through expansive windows, enhancing the inviting atmosphere. A side table and a plush armchair add to the comfortable seating options.
Condo in Dover
4.99 out of 5 average rating, 122 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

Guest favorite
The exterior of the condominium building is showcased, featuring three levels with large windows that allow natural light in. A central staircase leads to the entrance, flanked by green grass and small shrubs, creating a welcoming appearance.
Condo in Stratton
4.94 out of 5 average rating, 104 reviews

Great 2 bedroom condo at Stratton Mountain

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, 151 reviews

Cozy condo within walking distance to the slopes.

Guest favorite
A cozy living room features warm wooden paneling and a plush sofa facing a mounted flat-screen television. A circular coffee table sits in the center, complemented by a floor lamp and a side chair. A fireplace adds a comforting touch, creating a welcoming space.
Condo in Ludlow
4.94 out of 5 average rating, 151 reviews

Lovely 1-Bedroom condo with indoor fireplace!

Superhost
A comfortable living area showcases a gas fireplace beneath a large television mounted on the wall. A dark sofa sits beside a small coffee table, and light flows in through a glass door, which is accented by sheer curtains. Decorative elements enhance the space.
Condo in Dover
4.84 out of 5 average rating, 127 reviews

Walk to Mt. Snow-Spa-Summer Pool

Top guest favorite
The exterior showcases a two-story condo surrounded by greenery. A pathway lined with gravel leads to the entrance. Flowering plants and shrubs are visible along the pathway, and a lamp post adds a lighted accent. The condo features a mix of dark and muted colors with a welcoming porch.
Condo in Dover
4.92 out of 5 average rating, 131 reviews

3 Story Condo - 5 Minutes to Mount Snow!

Guest favorite
A view of the snow-covered path leading to the ski slopes is framed by the C Building’s balconies. Sunlight casts long shadows across the pristine snow, highlighting the tranquil winter scene. The surrounding area is clear and inviting, with ski signage visible in the distance.
Condo in Ludlow
4.92 out of 5 average rating, 148 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Ski-in/ski-out vacation rentals in Stratton

Guest favorite
An open living space features warm wooden walls and high beams, illuminated by natural light from skylights. A red sofa with patterned cushions is positioned near a round dining table. A cozy atmosphere is created with a lamp and decorative items on shelves.
Home in Dummerston
4.96 out of 5 average rating, 130 reviews

The Sugar House

Guest favorite
A green, grassy area is framed by tall, slender trees. Two benches are positioned on either side, offering a place to sit and admire the expansive view of distant hills and valleys under an overcast sky.
Apartment in Chester
4.89 out of 5 average rating, 503 reviews

Beautiful 2 Bedrooms in Mountains w/ full kitchen

Superhost
The exterior of a red cabin is surrounded by a snowy landscape. Large windows allow natural light to illuminate the front space, while a simple wooden bench rests on the porch. Pine trees are visible in the background, creating a serene atmosphere.
Cabin in Cavendish
4.94 out of 5 average rating, 163 reviews

The Cozy Little Red Cabin

Top guest favorite
A one-story cabin is partially enveloped by a blanket of snow, featuring a covered porch with orange railings. The entrance is accessible via a gentle ramp, while trees in the background provide a natural setting. Soft evening light gently illuminates the cabin.
Apartment in Ludlow
4.92 out of 5 average rating, 280 reviews

Okemo Vermont Getaway

Top guest favorite
A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.
Apartment in Charlemont
4.99 out of 5 average rating, 167 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

Guest favorite
The exterior showcases a rustic wooden building surrounded by lush greenery and vibrant shrubs. A winding stone path leads to the entrance, while large glass doors provide a welcoming view into the interior. The setting is serene and integrated with nature.
Apartment in Londonderry
4.96 out of 5 average rating, 587 reviews

Vermont Getaway Apartment

Top guest favorite
A cozy bedroom features a spacious bed draped in a soft, dark blanket. The walls are adorned with a captivating array of framed artwork, showcasing various styles. A bedside table holds a lamp, and a curtain partially covers a window, allowing natural light to filter in.
Place to stay in North Adams
4.93 out of 5 average rating, 258 reviews

Freemans Grove Benevolent Society Walk to MoCA

Top guest favorite
A mid-century modern home set among lush greenery features a stone foundation and large windows. A brick chimney rises above the roofline, while several wooden Adirondack chairs are positioned on a stone patio, providing a relaxing outdoor space to enjoy the surrounding nature.
Home in Cavendish
5 out of 5 average rating, 121 reviews

Midcentury Hillside Retreat - Summer Paradise

Quick stats about vacation rentals in Stratton

  • Total rentals

    180 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    5K reviews

  • Family-friendly rentals

    150 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    50 properties have a pool

Frequently Asked Questions

  • Do townhouse rentals in Stratton have free parking?

    Absolutely! We offer over 20 townhouse rentals with free parking in Stratton. Enjoy a tailored experience with all the comforts you desire.

  • Do townhouse rentals in Stratton have wifi?

    Absolutely! We offer over 20 townhouse rentals with wifi in Stratton. Enjoy a tailored experience with all the comforts you desire.

  • 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!

  • 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 house rentals in Stratton?

    Experience the best of Stratton with our house rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

  • 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 free parking, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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 house rentals in Stratton have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Stratton. Enjoy a tailored experience with all the comforts you desire.

  • Do townhouse rentals in Stratton have a kitchen?

    Absolutely! We offer over 20 townhouse rentals with a kitchen in Stratton. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

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  4. Windham County
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