Holiday houses in Surry

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Top-rated holiday rentals in Surry

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Superhost
An open concept living space features four arched windows that allow ample natural light. Wooden floors complement the revealed post and beam construction. A wooden dining table is centrally placed, with a cozy seating area in a corner, creating a relaxed environment.
Home in Putney
4.89 out of 5 average rating, 250 reviews

Spacious Loft with View

Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

Top Guest favourite
A spacious living area features eclectic furniture, including vibrant green and neutral-toned seating. A round glass table sits at the center, surrounded by a patterned rug. Walls are adorned with framed black-and-white art, and large windows allow natural light to fill the space.
Apartment in Putney
4.9 out of 5 average rating, 156 reviews

Hip & Cozy Storefront

Ground-level historic storefront turned into a private, hip place to sleep. Nestled in the village of Putney, VT it is just a walk to restaurants, General Store, nature trails and Next Stage Theater-short drive to Putney School, Landmark College & The Greenwood School- huge bathtub, movie screen, kitchenette with fridge, handicap accessible. Can sleep 3 or more upon request. The ski resorts of Okemo, Mt. Snow, Magic Mountain, and Stratton are not far~ making Putney a perfect ski get-a-way spot.

Guest favourite
A rustic building with wooden siding is partially surrounded by a foggy landscape. An elevated deck with rocking chairs invites relaxation. The entrance features glass doors flanked by large windows, allowing natural light to illuminate the interior. Surrounding greenery creates a serene atmosphere.
Home in Putney
4.93 out of 5 average rating, 425 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Guest favourite
A cozy reading nook is featured with a wooden table surrounded by two wooden chairs. The background showcases a wall lined with a variety of books, while soft natural light enters through a nearby window.
Cottage in Keene
4.83 out of 5 average rating, 109 reviews

The Library: Seasonal Stays

The Library is a two bedroom home with a granite kitchen, laundry, and a full and a half bathroom. It features thousands of books across many genres, from poetry to fiction. So if you like the smell of an old bookstore then this is the place for you! The steps to the second floor are very steep and narrow. The cottage is within walking distance to the shops and restaurants of Central Square Keene. Great place to get away to, or work from home with our Spectrum provided fast wifi internet.

Guest favourite
A comfortable white sofa with decorative pillows is positioned against a light wall. A small, light-colored side table holds a potted plant. Natural light streams in through a nearby window, illuminating the wooden floor and a blue woven rug beneath.
Apartment in Dummerston
4.95 out of 5 average rating, 253 reviews

HeART Barn Retreat

Peaceful, romantic retreat in this stunningly large and magical barn. This 1850's historic remodeled barn apartment is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

Superhost
The exterior of a wooden cabin is displayed amidst a snowy landscape. The structure features a sloped roof with skylights and a covered entrance that offers protection from the elements. A vehicle is parked nearby, and snow covers the ground and surrounding trees.
Cottage in Putney
4.81 out of 5 average rating, 290 reviews

The Cottage, a house built for guests.

In the village there is a wonderful farm to table restaurant, the Gleanery. A local pub, friendly, great food with indoor and outdoor dining & pub. The General Store, is the oldest continually run general store in Vt. The Next Stage, Yellow Barn, Sandglass Theater, these places provide an amazing collection of visual, musical, spoken word and world renowned art and artist to experience. These cultural event locations are but a mile away for the Cottage I hope you choose for your stay.

Guest favourite
The compact kitchen features modern appliances, including a microwave and refrigerator, paired with wooden cabinetry and a dining area. Light-colored wood flooring extends throughout, and a staircase leads to the sleeping loft above. Decor elements include framed artwork and a vase of flowers positioned on the counter.
Tiny home in Brattleboro
4.86 out of 5 average rating, 225 reviews

Sweet Vermont Tiny Home Get Away

Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

Top Guest favourite
A spacious sleeping area is highlighted by large windows dressed in soft curtains, allowing natural light to fill the room. The bed features a checkered blanket with decorative pillows, paired with a simple side table and a small plant, enhancing the cozy ambiance.
Apartment in Brattleboro
4.98 out of 5 average rating, 147 reviews

Bright and Modern Chestnut Street Apartment

Enjoy a unique stay at this central, beautifully-remodeled apartment in quaint Brattleboro, Vermont. The apartment is attached to the back of the charming 1914 home where I live, and has a private, separate entrance so guests can come or go as they please. This carefully-curated apartment includes tasteful decor, a well-appointed kitchenette, organic cotton sheets, and natural bath products. Just off Hwy 91, the apartment is located in the quiet, historic neighborhood of Esteyville.

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, 721 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
4.94 out of 5 average rating, 612 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
Farm stay in Gilsum
5 out of 5 average rating, 13 reviews

Cozy Studio at White Brook Farm

Enjoy a private stay surrounded by natural beauty at the historic 1806 White Brook Farm. A short drive to Keene with its restaurants, shops and Universities. Conveniently hike and bike the nearby trails from the property, and relax in the gardens while taking in the farm and surroundings. This is a 2nd floor apartment, inaccessible to wheel chairs.

Top Guest favourite
A bedroom features green walls, with large windows dressed in light curtains allowing natural light to filter through. A wooden bed with white bedding is positioned near a yellow dresser. Two comfortable armchairs are provided, complemented by a floor lamp for additional lighting.
Apartment in Saxtons River
4.84 out of 5 average rating, 208 reviews

Apartment on Main Street

One bedroom apartment with kitchenette (mini-fridge, coffee maker, microwave, dishes etc.), full bathroom with laundry, and open living space. I am an English teacher, so there are lots of books! Apartment is located in the Village of Saxtons River- within easy walking distance from the Market, Vermont Academy, our new Park, and Main Street Arts.

Popular amenities for Surry holiday rentals

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