Vacation rentals in Surry

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Top-rated vacation rentals in Surry

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Top guest favorite

The exterior of Boulder House is presented, showcasing a modern black facade with large windows. A spacious deck is visible, furnished with two chaise lounges and chairs. Surrounding boulders and colorful fall foliage create a natural and inviting environment.

Cabin in Stoddard

4.98 out of 5 average rating, 103 reviews

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Guest favorite

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

4.88 out of 5 average rating, 206 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 favorite

A welcoming porch is presented, featuring a combination of seating options including a cushioned chair, a rocking chair, and a white wicker chair. Wooden steps lead up to double glass doors framed by warm wood panels, inviting guests into the space.

Home in Putney

4.94 out of 5 average rating, 394 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 favorite

An iron bridge spans a flowing river, supported by multiple stone pillars. Waters cascade over large rocks in the foreground, creating a natural landscape. The setting sun casts a warm glow, highlighting the textures of the bridge and the surrounding flora.

Apartment in Bellows Falls

4.94 out of 5 average rating, 239 reviews

Village Flat with Antique Billiards

Charming and spacious first floor, 3 Bedroom, 1 Full Bath apartment. Sleeps 5 (1 King, 1 Queen and 1 twin). It is nestled in the center of the Bellows Falls village, a short 5-minute walk to downtown, where you will find great little shops and eateries. We are centrally located in Southern Vermont ~ 40 min from several ski areas (Okemo, Magic, Bromley, Stratton, etc.) about one hour from Killington Resort, Mount Snow, and Mount Sunapee (NH), and ~ 20 mins from Brattleboro, VT, or Keene, NH.

Superhost

A bathtub is positioned beside a large window, offering views of the surrounding greenery. Natural light filters through sheer curtains, illuminating the tub and a neatly rolled towel placed nearby.

Cottage in Putney

4.82 out of 5 average rating, 271 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.

Top guest favorite

The treehouse stands elevated among tall trees, featuring a warm wooden exterior and large windows that allow natural light to fill the interior. A deck extends from the structure, leading to a fire pit area surrounded by gravel.

Treehouse in Putney

4.99 out of 5 average rating, 122 reviews

Treehouse Haven in Putney-All Seasons

Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting toilet ☽ Tea & local coffee ☽ Hot outdoor shower ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Visit for romance, time with the family, a retreat from the business of life, or even a remote work sanctuary.

Guest favorite

A night sky displays a gradient of purple and dark blue tones, with stars scattered across the expanse. Silhouettes of power lines extend from the foreground into the distance, contrasting against the celestial backdrop.

Camper/RV in Guilford

4.93 out of 5 average rating, 139 reviews

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for up to two adults and one kid (63" long fold down couch).

Top guest favorite

The image captures a serene landscape with lush green grass and a large tree's shadow. In the background, two farm buildings are visible alongside a field with tall grass, under a soft pastel sky at dusk.

Guest suite in Westminster

4.96 out of 5 average rating, 55 reviews

COZY FARMHOUSE SUITE

Take it easy at this unique and tranquil getaway nestled in a revolutionary historically significant village. You can experience farm living while still close to Rte 91, an Amtrak station and the Connecticut river for fun water activities. This recently renovated studio has a private entrance with parking right outside. Fully equipped kitchen. Bathroom with tiled shower stall, easily accessible. The beautiful sleeping nook is perfect for two. Adorable sitting and dining/work areas.

Top guest favorite

A wooden chicken coop is visible, featuring a rustic design with a small door and decorative elements. A fenced area surrounds the coop, offering a view of plants and a bright yellow chicken statue. Lush greenery and trees provide a natural backdrop.

Barn in Chester

4.99 out of 5 average rating, 644 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. We are as close or as far away as you would like us to be with our house right next door.

Guest favorite

A loft bedroom within an A-frame structure displays a spacious bed with a white comforter and decorative pillows. A patterned rug is placed beneath the bed, and large windows frame scenic views. Soft, natural light filters through the space, enhancing the cozy atmosphere.

Chalet in Stoddard

4.95 out of 5 average rating, 263 reviews

Highland Haus AFrame Lake Access Vintage 70s Charm

Authentic 1975 A-frame chalet nestled in peaceful Stoddard countryside. This cozy cabin sleeps 5 with two wood stoves and full kitchen. Perfect rural retreat just 2 hours from Boston! Explore nearby hiking trails, swimming spots, and fishing areas. Summer bonus: complimentary canoe access! Highland Haus offers a tranquil escape with vintage charm. Note for winter visitors: Shedd Hill Road requires AWD/4WD due to steep terrain. Your cozy retro hideaway awaits!

Guest favorite

A cozy seating area consists of two Adirondack chairs positioned near a crackling fire pit surrounded by smooth stones. The bright white cottage stands in the background, framed by autumn foliage under a clear blue sky.

Tiny home in Putney

4.94 out of 5 average rating, 752 reviews

Honeycrisp Cottage - A Tiny Timber Frame

Honeycrisp Cottage a Tiny Timber Frame is a bright, energy-efficient dwelling nestled on 9 acres overlooking a beautiful forested mountain & trails to explore along a brook. A peaceful getaway retreat equipped with a living room, a king bed, a loft with a queen bed, a full kitchen, & a full bathroom. *Please No Smoking On The Property Mt. Snow - 50 mins Okemo - 50 mins Stratton - 1 hr Killington - 1 hr 20 mins

Guest favorite

A spacious living area is depicted with a comfortable brown couch adorned with patterned cushions. A rustic coffee table is central to the space. The kitchen area features dark cabinetry and a variety of decor, complemented by artwork on the walls and plants throughout.

Apartment in Town of Rockingham

4.96 out of 5 average rating, 204 reviews

Gorgeous 1-Bedroom Space in Historic Bellows Falls

Enjoy a stylish experience at this centrally-located place. Bellows Falls is a historic village located in Southern Vermont. Once a booming mill town, now a quaint picturesque village with shops, restaurants, and more. The space is located right in the center of town with plenty of space for those seeking to unwind in a small New England village.

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Popular amenities for Surry vacation rentals

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Other great vacation rentals in Surry

Top guest favorite

An aerial view captures the classic farmhouse nestled within lush green fields and surrounded by trees. A red barn with a metal roof is visible nearby, and the expansive landscape extends towards distant mountains, showcasing the serene rural setting.

Home in Walpole

5 out of 5 average rating, 70 reviews

Walpole NH Peaceful Farmhouse Getaway-VT/NH Border

LoribethRating, 5 stars8 months ago

Stunning property with beautiful views and tons of charm. Very warm and friendly quintessential New England farmhouse.

Top guest favorite

The open concept living area features large windows that invite natural light and offer views of the surrounding trees. A mix of seating options, including a green and brown sofa, is arranged around a central rug. The kitchen is visible in the background, equipped with modern appliances.

Cabin in Lempster

5 out of 5 average rating, 14 reviews

Modern & peaceful lake house - swim/hike/relax

RobertRating, 5 stars3 months ago

Great stay at Grateful Ledge! Audrey and Josh were excellent hosts, and were very responsive and communicative throughout our stay. The home was clean, open layout, modern and very comfortable. All the comforts of home including a new Weber grill. Off the beaten path with a private and peaceful location. Would stay again.

Guest favorite

The cottage exterior features a wooden facade with a green metal roof, framed by vibrant trees. A covered porch with potted flowers welcomes visitors, while large windows allow natural light to fill the space. The peaceful setting highlights the connection to nature.

Cabin in Guilford

4.96 out of 5 average rating, 71 reviews

Guilford Grove Cottage

ElizabethRating, 5 stars4 days ago

We truly loved staying in this beautiful, cozy cabin. It was just the right size for the two of us, and very comfortable. The view of trees and wildflowers was lovely and refreshing. It was also fun to have a couple of cats walk across the porch each day! Joel was very proactive and friendly, which we greatly appreciated.

Guest favorite

An outdoor space features a fire pit surrounded by log seating, with flames crackling in the center. In the background, a deck with steps is visible, above neatly stacked firewood. Bistro seating is arranged on gravel, complemented by greenery and nearby structures.

Apartment in Putney

4.97 out of 5 average rating, 97 reviews

Minimal organic hideaway inspired by nature

ItaRating, 5 stars2 weeks ago

Katherine’s space was so cozy! It was exactly what I needed for a retreat from daily life. I found both the loft and the daybed very comfortable. There were dimmers on most of the light fixtures, which was important to me because I like low-light settings. The kitchen included a counter with stools and was really quite beautiful. This Airbnb was within walking distance to a local restaurant, the general store and a food co-op. I decided not to rent a car because I was there for R&R., however , if you had a car, just a few minutes outside of town you would see beautiful trees all with leaves in there spring splendor. You could get to Brattleboro in about 20 minutes if you’re looking for more choices of restaurants.. (I decided to take the train up so I took a taxi to the Airbnb from the train and back to the train at the end of my trip.). Although it rained most of the time I was there, it was perfect for my goal of R&R.

Guest favorite

A well-lit interior hallway features a vintage-style clock on a tripod stand, indicating the time with clear markings. Sunlight streams through an open door, illuminating the adjoining bedroom, which includes a spacious bed and a glimpse of a closet area.

Apartment in Keene

5 out of 5 average rating, 20 reviews

The Darling Suite

JoshuaRating, 5 stars5 months ago

Convenient and easy access to Keene and the surrounding area. We spent Christmas week and the first floor unit was perfect for our needs as my mother has a walker and it only required two stairs up from the driveway! I would def recommend this place!

Guest favorite

A serene outdoor space features three wooden Adirondack chairs arranged around a natural stone fire pit, set amidst a lush green landscape. Surrounding trees provide a sense of privacy and tranquility, with dappled sunlight filtering through the foliage.

Guest suite in Putney

4.96 out of 5 average rating, 68 reviews

Peaceful Country Retreat on 15 Secluded Acres

StephenRating, 5 stars1 week ago

A really wonderful home to stay in;peaceful and an overall feeling of calm just like Liz and Matt and their wonderful daughter who were all so easy to chat with. The accommodation really did make you feel at home and was so quiet and was exactly as described plus!

Superhost

A compact bathroom features light-colored tiled flooring and neutral-toned walls. A shower curtain with blue stripes encloses the shower area. A small vanity with a sink and mirror is positioned beside a toilet, while a decorative stool and neatly arranged towels complete the space.

Home in Town of Rockingham

4.63 out of 5 average rating, 43 reviews

Simple 2+ bed, no frills, all necessities covered!

MuditRating, 5 stars7 months ago

Great place, especially for the budget. It was clean, comfortable, and had everything we needed for a relaxing stay.

Superhost

The exterior of a historic house is displayed, featuring dark wooden siding and classic architectural details. Tall columns support a prominent porch, surrounded by lush greenery. A mix of vibrant shrubs and trees frames the front of the property, offering a sense of privacy and natural beauty.

Apartment in Keene

4.81 out of 5 average rating, 80 reviews

Rustic Modern One Bedroom: Seasonal Stays

DanielleRating, 5 stars1 month ago

We loved our stay here! The place was so cool! We love that it was close to everything and walkable to graduation. It was a little tricky to find at first because it's in between two houses so maybe list the color, black because we were walking around in the dark trying to find it LOL but parking is super close and you can unpack in the driveway. The couch is comfortable to sleep on and there were plenty of blankets and pillows! And we love the Retro Style!

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Vacation rentals in Surry

Top-rated vacation rentals in Surry

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