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House vacation rentals in Brattleboro

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Top-rated house rentals in Brattleboro

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A serene scene features a spacious house nestled beside a tranquil pond. Vibrant autumn foliage enhances the landscape, with a mix of orange, yellow, and green trees lining the property. The grassy area invites exploration, while reflections on the water add to the peaceful ambiance.

Home in Grafton

4.94 out of 5 average rating, 122 reviews

The Grafton Chateau

Welcome to the Grafton Chateau, a gorgeous secluded and private country retreat for all of your family and friends. With six bedrooms and a den, four baths, two fireplaces, a sauna and a large private pond beautifully situated on 67 acres of woodlands, the Grafton Chateau is the perfect comfortable home base for ski trips, hiking, antiquing, or just enjoying the scenery while you sit around the fire pit. The garage has outdoor recreation gear, like snowshoes and sleds. The den has a variety of toys, and games for kids and adults. The whole house, sauna house, barn and all 67 acres are all yours! We are always available by phone, text, or email if you have any questions. Grafton is just about the most charming Vermont town you can find and is convenient to four ski mountains and every other outdoor activity you can imagine.

Top guest favorite

The exterior of the country home is showcased, depicting a two-story structure with a welcoming porch. Lush green grass surrounds the house, and vibrant flowers bloom along a stone pathway, enhancing the natural beauty of the tranquil setting.

Home in Shelburne Falls

5 out of 5 average rating, 100 reviews

Charming Brookside Artisan Home

Relax, work & play in this peaceful country home built by a renowned furnituremaker and filled with handmade furniture and art. Explore the countryside, listen to the babbling brook & visit the many local family farms. There is a large firepit and plenty of outdoor activities at your doorstep, including biking, hiking, and x-country skiing. Come get away from it all while being only 10 minutes to Greenfield and the quaint village of Shelburne Falls. Easy 30 minute drive to the five college area.

Top guest favorite

A spacious living room features a vaulted ceiling and an arched window that allows natural light to flood the space. Comfortable seating arrangements include two red sofas and a patterned area rug. Shelving units display decorative items, while a media system is positioned above the fireplace.

Home in Brattleboro

4.93 out of 5 average rating, 120 reviews

Modern Spacious Home with Mountain Views

Modern Home in Brattleboro with mountain view & many extras: Italian-Marble master-suite, Jacuzzi/Shower for 2, walk-in closet, king bed, grill, heated garage, cable, WiFi. Open-concept living room w/ cathedral ceiling, office, & movie screen. Large open kitchen w/ wine fridge. Second bedroom w/ loft. Explore hiking trails from backyard. Pets ok! 3 mins from Vermont Country Deli & I91 Exit 2. Walking distance to dog park, swimming holes. Downtown: 4 mins Mount Snow: 40 mins Stratton: 54 mins

A white cottage is framed by lush greenery and colorful flowers, including yellow irises and bluebells. Several large windows reflect sunlight, and a wooden bench sits invitingly among the vibrant plants, enhancing the serene garden setting.

Home in Townshend

4.97 out of 5 average rating, 120 reviews

Lawrence Cottage

Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

Top guest favorite

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.

4.94 out of 5 average rating, 399 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.

Top guest favorite

A rustic living room features a large stone fireplace and wooden beams overhead. A red sofa with decorative pillows sits across from a unique wooden coffee table, which is centered on a colorful area rug. A lantern with candles adds a warm touch to the space.

Home in Wilmington

4.99 out of 5 average rating, 208 reviews

Vermont Sugar House Retreat

Stay at this unique rustic Vermont getaway. Nestled on a quiet hill in Wilmington, this private retreat will serve as the perfect home base for your Vermont adventures. You'll have the house to yourself without a neighbor in sight. While very private and surrounded by beautiful forest, this house is still only a short 5 minute drive from downtown Wilmington. The house is built around an enormous one-of-a-kind natural stone fireplace that was formed atop the old foundations of a sugar house.

A comfortable living area is highlighted by a light grey sofa and an armchair. A small coffee table sits on a patterned area rug. Natural light enters through multiple windows, illuminating the space. A side bookshelf holds an assortment of books, completing the cozy atmosphere.

Home in Chesterfield

4.91 out of 5 average rating, 116 reviews

Governer's Brook Camp - 2 Bedroom

Renovated camp, 800 sq ft, near Brattleboro VT & Lake Spofford NH. Hiking trails start at the backyard. I15 minutes to Brattleboro, 5 minutes to the boat ramp on Connecticut River, 15 minutes to Lake Spofford, and 50 minutes to Mt. Snow. Across the road is a (seasonal) tumbling waterfall and gorge called “the Devils Den”. The backyard leads to woodlands with miles of trails. Enjoy a relaxing evening by the firepit overlooking the brook. Or outdoor cooking on a propane grill. ...2 Kayaks.

Top guest favorite

A white fireplace with a rustic brick surround serves as a central feature. Above, a shelf displays decorative bowls and books, while soft sunlight casts shadows across the surface. A lamp with a patterned shade stands nearby, adding a touch of warmth to the space.

Home in Brattleboro

4.89 out of 5 average rating, 160 reviews

Cozy Home for 2-5 People in Vermont

Comfortable house for 2 to 4 people (two queen-sized beds) and a pull-out couch for a 5th person and a self-inflatable bed. Located in a quiet neighborhood. There are two main bedrooms with queen beds in each. There is also a pull-out couch in the room with the fireplace though it is not as comfortable as the self-inflatable bed (and deflatable) in the house. Fast Wi-Fi from Xfinity. Easy to get into Brattleboro Center and an excellent location for exploring Southern Vermont.

Top guest favorite

An open-concept kitchen features a central island with bar seating for two, surrounded by wooden cabinetry and ample natural light from large windows. A dining area with a table for six is visible, complemented by wooden chairs and a cozy living space in the background, showcasing a comfortable setting.

Home in Newfane

4.98 out of 5 average rating, 138 reviews

Peaceful cabin close to skiing & Brattleboro

Our 4BR/2BA (+ outdoor summer shower) home embraces the best of Southern VT. Skiing (20 min to Mt. Snow; 35 min to Stratton), river swimming holes, hiking, biking, art galleries and great restaurants nearby. Open concept space, cook's kitchen, jet bathtub, beautiful gardens, winter hot tub off deck, and large patio and fireplace give a homey feel. Secluded from neighbors but close to amenities, this home is a comfortable and peaceful retreat for your next gathering.

A dining area is showcased with a round wooden table surrounded by four white chairs. Natural light illuminates the rich hardwood floors, while a wooden cabinet with glass doors adds storage. The kitchen is visible in the background, featuring modern appliances and a warm atmosphere.

Home in Brattleboro

4.94 out of 5 average rating, 222 reviews

Frosted Willows

Your family will be close to everything at this sunny, centrally located home on the Whetstone Brook. Just 0.6 miles from downtown Brattleboro, you can walk to shops, cafés, galleries, and more. Nestled in a quiet neighborhood, the house offers a peaceful place to relax after a day of exploring. Listen to the brook from the backyard, enjoy local adventures, and settle into a space that feels like home—perfect for a weekend getaway or a longer Vermont stay.

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

The Sugarhouse is a fully furnished one bedroom cabin, with a complete kitchen, bathroom with shower and open living / dining room area. It is located on a quiet Vermont country road bordered by historic New England dry stone walls, maple trees, and the beautiful Scott Farm. You can hike, bike, or snowshoe right out the front door. While you’ll feel a world away, you’ll be only 5 miles from Interstate 91 and 10 minutes from Brattleboro or Putney.

Top guest favorite

A spacious deck extends from the house, equipped with an umbrella and several chairs, providing a view of the encompassing greenery and mountains. The home's exterior features warm brown siding and solar panels on the roof, set against a bright blue sky.

Home in Brattleboro

4.94 out of 5 average rating, 125 reviews

Spacious Brattleboro home on river, walk to town

Look no further for the perfect retreat. This spacious area for AirBnB guests (approx 3,000 sq feet) consists of 4 bedrooms, 4 bathrooms (2 en-suite), a formal living room & dining room, a TV-room, and kitchen (eat-in) with family area opening onto a deck. Dramatic river & Wantastiquet Mountain views (foliage or greenery). Ten minute walk to Brattleboro Main Street.

Vacation rentals for every style

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Popular amenities for Brattleboro house rentals

Free parking on premises

Air conditioning

House rentals with a pool

A serene backyard features a heated saltwater swimming pool, surrounded by lounge chairs and a safety fence. Verdant landscapes and a blue sky provide a tranquil backdrop, while a red barn is visible in the distance, adding to the rural charm.

4.98 out of 5 average rating, 194 reviews

Magical Farm Getaway - a must visit!

Home in Colrain

4.89 out of 5 average rating, 131 reviews

The 1770 House

A Colonial home is positioned on a green lawn, showcasing a charming brick façade and a classic porch. Large trees provide shade, while an American flag is displayed proudly by the door. Nearby, a design studio is visible, highlighting the spacious front yard.

4.93 out of 5 average rating, 214 reviews

The Brick House on Washington Street

The spacious great room features a wood-burning fireplace and is furnished with two comfortable sofas and a wooden coffee table. A large flat-screen TV hangs on the wall, and natural light emanates from the surrounding windows. A dining area with a circular table is visible in the background.

4.91 out of 5 average rating, 101 reviews

Walk to Okemo Ski Lift - Private Classic VT Ski Ch

An outdoor pool area features a large swimming pool surrounded by a sun deck lined with lounge chairs. Green trees form a natural backdrop, while a playground structure stands off to one side, offering recreational opportunities for guests.

Home in Wilmington

4.81 out of 5 average rating, 59 reviews

Mountain Paradise 4BR Hot Tub Pool 10min Mt Snow

A sizable pool is surrounded by a concrete deck, featuring multiple lounge chairs for relaxation. A shaded area is provided by an umbrella, and a building with sliding glass doors stands in the background, offering easy access to the outdoor space.

Home in Granville

4.93 out of 5 average rating, 108 reviews

Historic 1850’s Renovated Farmhouse w/ Pool!

The pool area is framed by lush greenery, featuring a large in-ground pool with a slide. A colorful inflatable float is seen in the water. A shaded patio table with chairs provides a space for relaxation, alongside a sun umbrella that casts shade over the area.

Home in Williamstown

4.89 out of 5 average rating, 220 reviews

Hollywood Bungalow in the Berkshires #C0191633410

Home in Wilmington

4.84 out of 5 average rating, 171 reviews

The Vermont Barn (Mount Snow)

Weekly house rentals

Top guest favorite

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

5 out of 5 average rating, 17 reviews

Charming Vermont Schoolhouse

A charming late 19th century farmhouse is presented, featuring a red exterior with two dormer windows and a central door. Lush greenery surrounds the entrance, and a stone wall lines the property. The clear blue sky adds to the inviting atmosphere.

4.95 out of 5 average rating, 22 reviews

19th Century Farmhouse Retreat

A sunlit living room features a wood stove surrounded by natural wood flooring. A rocking chair sits beside a dark trunk, while a lamp and a vase of flowers add warmth. Two large windows provide ample light, and a cozy sofa is positioned nearby.

Home in Brattleboro

4.75 out of 5 average rating, 28 reviews

Eco Friendly Garden House

A bright living area is furnished with a brown leather chesterfield sofa and a wooden coffee table. A vibrant rug adds warmth to the wood floor. Large windows offer views of the surrounding hills, while a cozy wood stove provides a focal point in the room.

Home in Brattleboro

4.89 out of 5 average rating, 9 reviews

4 BR home surrounded by hiking w Amazing views!

Top guest favorite

A charming exterior of the house is captured, featuring light-colored siding and a welcoming porch. Lush greenery surrounds the property, while a wooden well adds character to the front yard. Stone pathway leads to the entrance, enhancing the inviting atmosphere.

Home in Chesterfield

4.95 out of 5 average rating, 58 reviews

The River House

Top guest favorite

The exterior of the cottage is partially obscured by tall, colorful wildflowers swaying in the breeze. Sunlight illuminates the scene, highlighting the serene setting surrounded by greenery and trees, with a clear blue sky in the background.

Home in East Dover

5 out of 5 average rating, 54 reviews

Magical Retreat Cottage - Waterfalls everywhere

Top guest favorite

A warm living area features a plush, patterned sofa and a comfortable armchair arranged around a wooden coffee table. A stone fireplace adds a rustic touch, while a large window invites natural light into the space. Stairs lead to the upper level.

Home in Newfane

5 out of 5 average rating, 14 reviews

Winchester Stables Farmhouse

A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.

Home in Guilford

4.91 out of 5 average rating, 57 reviews

Vermont Mirror House

Private house rentals

A friendly sheep stands in the foreground, while several others graze in the green grass, near a charming farmhouse with white siding and large windows. The surrounding trees provide shade, contributing to the peaceful rural setting.

Home in Newfane

4.94 out of 5 average rating, 100 reviews

Clark Farm-2 Master-Suites, Great kitchen, views!

Top guest favorite

A spacious living room features a gas fireplace set against a dark brick wall. Large windows allow natural light to fill the area, highlighting minimalist furnishings including a leather couch, a coffee table with a striped runner, and a massage chair.

Home in Jamaica

5 out of 5 average rating, 14 reviews

Stylish Mountain Retreat w/ A/C & Tranquil Vibes

Top guest favorite

A wooden cabin is situated on a grassy area surrounded by trees, featuring a spacious deck with steps leading to the entrance. The roof is metal, and multiple large windows allow natural light to illuminate the interior.

Home in Northfield

5 out of 5 average rating, 13 reviews

Minimalist forest retreat

Top guest favorite

A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.

Home in Bennington

5 out of 5 average rating, 69 reviews

The Vermont Farmhouse+Charming Countryside Views

A tranquil bedroom features a spacious bed dressed in a light blue coverlet and flanked by two nightstands. A cozy throw is placed at the foot of the bed. Natural light enters through a window adorned with dark blinds, creating a calm atmosphere.

Home in Walpole

4.91 out of 5 average rating, 22 reviews

A Quaint Setting in the Center of Walpole Village

A modern wooden structure is situated on a grassy area, surrounded by vibrant autumn foliage. The large windows reflect the natural light and provide a view of the colorful trees in the background, emphasizing the serene woodland setting.

Home in Newfane

4.87 out of 5 average rating, 15 reviews

Relaxing Mountain Retreat with a View

Top guest favorite

A spacious deck overlooks a vibrant sunset, with an expansive view of rolling hills and trees under a partially cloudy sky. The area is enclosed by modern railing, and the deck's surface provides ample space for relaxation or gatherings.

5 out of 5 average rating, 16 reviews

Mountaintop Views, close to private schools, golf

A charming two-story home is presented in a deep blue, complemented by natural wood shingles. Surrounded by lush greenery, large windows allow ample light to illuminate the interior. The exterior features a welcoming entrance and is framed by tall trees, creating a serene atmosphere.

Home in Brattleboro

4.82 out of 5 average rating, 17 reviews

Cozy home in Brattleboro

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