Vacation rentals in Guilford

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Top-rated vacation rentals in Guilford

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Top guest favorite

The cottage, constructed with a rustic red facade, is surrounded by vibrant greenery. A metal roof complements the structure, while nearby ferns and trees enhance the natural setting. Windows invite light into the space, showcasing a serene, wooded atmosphere.

Home in Guilford

4.96 out of 5 average rating, 131 reviews

Green River Cottage-A Peaceful Country Retreat

Bask in the beauty of rural Vermont while nestled in the woods of a cozy cottage along the Green River. Sit on the front deck and enjoy the sounds of the river or stargaze while surrounded by the enchanting beauty of the rolling emerald hills. Right outside the door you can walk, bike or jog for miles on quiet scenic back roads. Located on a dirt road 20 min. from Brattleboro & just a few miles from the Mass border, our cottage is the perfect place to relax or enjoy all the area has to offer.

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, 163 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

A beautiful retreat is set amidst lush greenery, featuring a wooden structure with a welcoming entrance. A stone pathway leads through the garden, and the building is surrounded by various plants, enhancing the natural ambiance of the setting.

Guesthouse in Brattleboro

4.91 out of 5 average rating, 552 reviews

Mahalo Temple Retreat

Retreat in Mahalo's beautiful, private sound healing temple surrounded by nature, amongst streams, berry bushes, fruit & nut trees, medicinal plants and veggie gardens. We are set back just enough from a main road to find your serenity and yet close enough to civilization for human interaction and trails for hiking. Quiet and peaceful location just a few min off I-91 and just over 2 miles from the center of Brattleboro. A fun and quirky town with art cafes, restaurants, and great shops.

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, 278 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 favorite

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

4.87 out of 5 average rating, 193 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

Two white lounge chairs are positioned around a small black fire pit in a grassy area. Lush greenery and trees define the backdrop, while an open space creates a sense of privacy and tranquility.

Apartment in Brattleboro

4.99 out of 5 average rating, 153 reviews

River View apartment

Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .

Top guest favorite

An elevated wooden deck is surrounded by trees, featuring a canvas tent. Two red folding chairs are positioned nearby, alongside a hammock suspended between two posts. Sunlight streams through the leaves, highlighting the natural setting.

Treehouse in Guilford

4.99 out of 5 average rating, 164 reviews

Cozy tent in the trees on organic flower farm

Tuck yourself into a mature oak forest on the field’s edge of our flower farm, Tapalou Guilds. All-weather canvas tent is pitched with a comfy king mattress inside. Three elevated decks with chairs and a hammock give you options for relaxing and steeping in the forest vibe. Fully equipped outdoor kitchen with propane gas range. We provide potable water from our well. Outdoor shower with on-demand hot water. Simple outhouse with sawdust composting system is clean and convenient.

Guest favorite

A gently sloping lawn leads up to the light-colored building, framed by lush gardens and vibrant greenery. A pair of purple Adirondack chairs sits invitingly on the grass, offering a serene spot to enjoy the surrounding landscape.

Apartment in Marlboro Township

4.93 out of 5 average rating, 278 reviews

Shakespeare’s Folly Side Farm and AirBnB.

Located on a gorgeous south-facing hillside in Marlboro, VT, Shakespeare's Folly Side Farm is a light, airy, quiet apartment with stunning views, beautiful gardens, and walking paths. We have friendly goats and dogs, vegetable and flower gardens and a small orchard, with raspberries and blueberries. Free picking in the summer. A magical and inspiring place of rolling lawns and 40 mile views yet so close to the many rich cultural and recreational options in southeast Vermont.

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

4.94 out of 5 average rating, 595 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.

Guest favorite

A charming red cabin is nestled among lush green trees, surrounded by moss-covered ground. The exterior features multiple windows, allowing natural light to fill the space. A small shed is visible to the left of the cabin, enhancing the serene woodland setting.

Cabin in Guilford

4.95 out of 5 average rating, 174 reviews

Silver Brook Cabin

Waterfront setting in a relaxing, but convenient, location in southeastern Vermont. Photos and captions do the best job of describing our cabin, adjacent brook, and very nearby Green River with its covered bridge and swimming holes. The cabin is 20 minutes from Brattleboro with its many restaurants, shops, movie theater, and galleries. Not only is the immediate area wonderful for swimming, biking, and hiking, you can also simply relax with a good book or two.

Top guest favorite

A well-lit dining area features a small table set with dishes and glasses, illuminated by natural light from large windows. Two chairs are placed alongside the table, while a vintage painting hangs on the wall, adding a touch of charm to the space.

Cabin in Guilford

4.96 out of 5 average rating, 554 reviews

Serenity Now - Couples Retreat or Writer's Dream

COUPLES RETREAT or SOLO EXCURSION Perfect setting to swoon your partner or write the novel of your dreams. A romantic destination for Engagements, Honeymoons & Anniversaries. Guilford Vermont - no cleaning fee - Easy drive from Boston & NYC ROMANCE SPECIAL - Guests staying 4-nights or more, receive Vermont Made hard cider, cheese crackers and chocolate ($50.00 value) Ask me about ELOPEMENT & VOW RENEWAL CEREMONIES

Top guest favorite

A bright hallway extends through the upper level, featuring exposed wood beams and soft yellow walls. Vintage framed artwork is displayed alongside a small table with fresh flowers. A doorway leads to a cozy space lined with bookshelves, inviting quiet reading moments.

Barn in Guilford

4.99 out of 5 average rating, 131 reviews

The Carriage Barn

Situated on a 1792 Vermont farmstead, the original Carriage Barn is a thoughtfully renovated 2-bedroom cottage that blends historic charm with colorful, comfortable design. Located just 10 minutes from Brattleboro and 45 minutes to Mt. Snow (~1 hour to Stratton, Okemo, Bromley, and Magic Mountain), it’s a perfect home base for a cozy New England escape.