Vacation rentals in Brookline

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Top-rated vacation rentals in Brookline

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Top guest favorite
A cozy tiny cabin, constructed with wooden beams and a sloped roof, is situated among tall trees. The porch features a railing, inviting seating, and a lantern. Sunlight filters through the foliage, casting a soft glow on the forest floor covered in pine needles.
Treehouse in Brookline
4.98 out of 5 average rating, 257 reviews

Glamping Cabin with Hot Tub on Flower Farm

<b>Vermont's Most Wish Listed</b> ﹏﹏﹏ Nestled in a wooded grove on Tanglebloom Flower Farm, this unforgettable glamping-inspired farm stay invites you to escape the everyday & immerse yourself in nature - comfortably. Designed with a clear roof looking up to the trees and screened sides to let in the breeze, the handmade tiny cabin invites you to slow down. Explore southern Vermont's hikes, farmer's markets & swimming holes or stay put. Perfect for a romantic couples retreat or solo getaway.

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.
Home in Putney
4.93 out of 5 average rating, 417 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 cozy outdoor living area features wooden seating, including a swing and chairs surrounding a fire pit. The camper is positioned on a deck nestled among trees, providing a sense of seclusion. A small table is visible, completing the inviting gathering space.
Camper/RV in Guilford
4.94 out of 5 average rating, 175 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 two adults (queen bed) and one kid (63" long fold down couch).

Guest favorite
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
4.82 out of 5 average rating, 284 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.

Superhost
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
4.84 out of 5 average rating, 205 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 favorite
Exposed wooden beams frame the room, complemented by warm brick walls. A cozy fireplace sits centered against the wall, with decorative art above it. A comfortable chair and lamp are positioned nearby, while a television and small dresser provide functional elements in the living space.
Cottage in Newfane
4.99 out of 5 average rating, 256 reviews

Cozy Vermont Antique Sugar House with Fireplace

Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

Top guest favorite
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, 694 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.

Top guest favorite
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
4.95 out of 5 average rating, 601 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 favorite
A bright living area is filled with natural light from large wooden windows framed by greenery outside. A cozy couch is adorned with decorative cushions. A round coffee table features a candle and a vase of sunflowers, inviting relaxation in a serene setting.
Cabin in Putney
4.98 out of 5 average rating, 435 reviews

Serene Retreat in Nature w/ Woodfired Tub

A romantic and private getaway on a peaceful six-acre farm with views of fields and forest. ☽ Featured in STAY; Gorgeous Cabins of the East Coast ☽ Outdoor wood-fired hottub, surrounded by nature ☽ Elevated design; thoughtful lighting; deeply romantic ☽ Quiet & private; star-studded skies ☽ Woodstove, deck, reading nook, firepit ☽ Local's Area Guide with our favorite spots ☽ Strong wifi, no TV ☽ Scrupulously clean using unscented products

Top guest favorite
A living area features warm wooden walls and large windows draped with sheer curtains, allowing natural light to fill the space. A comfortable sofa sits adjacent to a television, with a vintage chest and decorative items adding character. A patterned area rug enhances the cozy ambiance.
Apartment in Newfane
4.88 out of 5 average rating, 160 reviews

Apartment at Five Ferns

A cozy spot perfect for quick romantic getaways and an equally comfortable base for longer adventures. Views out your windows show perennial flower gardens and trees. Queen mattress in a spacious bedroom, en-suite bathroom (shower), and a living/dining area with an equipped kitchen are all at your service. Enjoy our yard and trails along the river. We are an easy 5 minute drive to a fantastic restaurant and many more within 15 minutes of driving.

Top guest favorite
A charming red cabin is positioned amidst lush greenery, with a wraparound deck accessible from the front. Bright yellow flowers bloom in abundance in the foreground, enhancing the natural beauty of the serene setting.
Cabin in Newfane
4.95 out of 5 average rating, 195 reviews

Cozy Cabin in Southern VT

Take it easy at this tranquil getaway. Fall asleep to chirping bugs and wake up to birdcalls. This is a quiet, lovely cabin in Newfane VT. Read a book, walk the meditation circle, swing in the hammock, and explore all that Southern VT has to offer. Close to swimming holes, hikes, country stores, flea and farmers' markets, and ski mountains (Mt Snow and Stratton) Pets and children are welcome, but there is only one queen bed.

Guest favorite
The bedroom is designed with a spacious bed adorned with crisp white linens. A large triangular window provides a serene view of lush greenery outside, allowing natural light to fill the room.
Cabin in Townshend
4.96 out of 5 average rating, 177 reviews

Modern Cabin with Outdoor Spa on Vermont Farm

Romantic modern cabin with private hot tub on a 100-acre Vermont farm. This Scandinavian-style retreat features soaring windows, a king bed with luxury linens, a cozy fireplace, and a sleek kitchen. Perfect for couples seeking a peaceful getaway, farm stay, or eco-friendly escape. Soak under the stars, meet our friendly goats, and enjoy the beauty of southern Vermont from your light-filled solar-powered cabin.

Popular amenities for Brookline vacation rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Brookline