Vacation rentals in Guilford

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Top-rated vacation rentals in Guilford

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Top guest favorite

A wooden table displays a textured lampshade connected to a circular base with a pull chain. Beside it, a green glass vase holds dried hydrangea flowers, and an elephant figurine adds a decorative touch. The arrangement rests on a floral table runner.

Home in Guilford

4.96 out of 5 average rating, 126 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.

Superhost

An outdoor gathering area is surrounded by lush greenery, featuring a wooden fire pit and four seating options. Two curved wooden chairs and two bench-style seats are arranged around the fire pit, creating a cozy atmosphere for relaxation in nature.

Guesthouse in Brattleboro

4.92 out of 5 average rating, 529 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.

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.

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

4.88 out of 5 average rating, 164 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.

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, 141 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

An all-weather canvas tent is positioned on an elevated wooden deck surrounded by trees. A soft glow emanates from a wall-mounted light, illuminating the entrance. Steps lead up to the tent, which features windows that invite glimpses of the forest beyond.

Treehouse in Guilford

4.99 out of 5 average rating, 144 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.

Top guest favorite

An authentic log cabin is nestled among lush ferns in a wooded area. The structure features a wide porch with railing, several windows allowing natural light, and a chimney. The surrounding greenery enhances the cabin's secluded feel.

Cabin in Guilford

4.99 out of 5 average rating, 138 reviews

Rustically Romantic Cabin Near Sweet Pond

COUPLES RETREAT, SOLO ESCAPES & WRITER'S DREAM in Southern Vermont - No Cleaning Fee Perfect for ENGAGEMENTS, HONEYMOONS & ANNIVERSARIES Authentic log cabin tucked into a private wooded cove outside of Brattleboro. A short tranquil walk to Sweet Pond State Park. Biking galore and Kayaking nearby. A variety of hikes to choose from. ROMANCE SPECIAL Stay 4-nights or more & receive hard cider, cheese & chocolate. Ask Me About ELOPEMENT & VOW RENEWAL CEREMONIES

Top guest favorite

A light yellow exterior of a two-story building is visible, featuring a sloped roof and a garage door on the left. A manicured garden with shrubs and decorative elements is positioned near the entrance, along with a satellite dish mounted on the wall.

Condo in Brattleboro

4.93 out of 5 average rating, 353 reviews

Private & Quiet Studio Apt. in Vermont

Clean, comfortable , quiet and snug, this studio apartment is a great place to come and relax in. It has a comfy QUEEN size bed with a 40” LCD at its foot, a kitchen set up for cooking and a desk with a view of a green field. This apartment is situated on the ground floor of our detached garage. Our garage sits behind our home, well away from the street. We live in a residential neighborhood that is conveniently located near I91, Route 30, Route 9 and Downtown .

Guest favorite

A serene scene of a cascading waterfall flows into a calm swimming area, surrounded by lush greenery. Several individuals can be seen enjoying the water, while the grassy bank invites relaxation. The natural setting offers a peaceful spot for swimming and unwinding.

Cabin in Guilford

4.95 out of 5 average rating, 169 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

Barn in Guilford

4.99 out of 5 average rating, 126 reviews

The Carriage Barn

Situated on a 1792 Vermont Farmstead, the original Carriage Barn is a renovated 2-bedroom cottage that embraces historic building details within a comfortable and colorful design aesthetic. Located just 10 minutes outside of Brattleboro, Vermont, 45min to Mt Snow, and ~1hr to Stratton, Okemo, Bromley, and Magic Mountain.

Top guest favorite

An enclosed porch is furnished with a white rocking chair and various seating options adorned with colorful cushions. A woven storage box sits beside a patterned area rug that features large floral designs. Natural light filters through multiple windows, creating a bright atmosphere.

Apartment in Brattleboro

4.9 out of 5 average rating, 367 reviews

Quiet St in Town, gardens, terrace

Private entry, up wide covered stairs to open and enclosed porches, into newly renovated spacious open concept living and kitchen area. Separate large BR with queen-size bed has French doors that open onto the enclosed porch. A few blocks to downtown restaurants, food coop, and shops, walking distance to trails.

Top guest favorite

The expansive green lawn is visible, dotted with a red picnic table and four chairs. The scene is framed by the rolling hills and trees, creating a backdrop of Southern Vermont's greenery under a partially cloudy sky.

Guest suite in Guilford

4.97 out of 5 average rating, 152 reviews

Private, Quiet Vermont Studio With Mountain Views

Formerly a musician's retreat, the view from the studio looks out over the lovely Green Mountains of Southern Vermont. Well insulated for sound and comfort, the studio offers privacy, peace and quiet and a chance to relax in the serene beauty of the Vermont woods.

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Guest favorite

Home in Brattleboro

4.94 out of 5 average rating, 17 reviews

Bright, spacious country home

NathalieRating, 5 stars3 days ago

This home in the woods felt loved. The kitchen has so many cooking necessities and the bathroom was also well stocked. Alyssa’s home grown produce was more than expected. It was the quintessential VT experience.

Top guest favorite

A screened-in porch features an inviting wooden Adirondack chair, positioned next to a rustic table set for dining. Soft lighting fixtures hang above, and additional seating can be observed in the background through large windows, creating a connection with nature.

Apartment in Brattleboro

5 out of 5 average rating, 13 reviews

Cozy Country Apartment with View

MichaelRating, 5 stars1 week ago

Beautiful little place with a cool history in the hills outside Brattleboro. Nice views from the screened-in porch, even on hazy days, and plenty of birds to see if you're a birder like me. It's a short 15 minute drive into the relative bustle of Brattleboro, but it doesn't feel like it--you feel completely like you are up in the mountains. The road is quiet but not deserted. The place was clean, check-in simple and easy to follow, and the host was communicative, making sure everything was going alright during our stay. Would definitely visit again!

Guest favorite

A private deck is shown with a dining table set for four, surrounded by comfortable chairs. Potted flowers add a touch of nature. Nearby, a single green chair rests against the house, creating a cozy outdoor space overlooking the calming landscape.

Guesthouse in Brattleboro

4.93 out of 5 average rating, 70 reviews

Casita by the Green: Quiet, Country, close to town

GuangliangRating, 5 stars3 months ago

We had a fantastic stay at Cyndi’s place! She is an incredibly helpful and thoughtful host, going above and beyond to make sure we were comfortable. She even provided us with milk and cream, which was such a kind touch. The accommodation was clean, cozy, and well-equipped, making our stay even more enjoyable. Highly recommend staying here if you’re looking for a welcoming and hassle-free experience!

Guest favorite

A charming cabin, labeled 'River Camp,' features a wooden exterior and a spacious porch adorned with potted flowers. The surrounding greenery enhances the natural setting, while a small table with chairs is visible on the porch, inviting relaxation and enjoyment of the outdoors.

Cottage in Brattleboro

4.97 out of 5 average rating, 31 reviews

On the Water at North Bridge Cove

StephRating, 5 stars3 weeks ago

2nd time staying here, lovely little spot on the river. Well-priced and met our needs. Best for 1-2 travelers and folks who either have a car or don't mind the easy walk into town. I'll likely stay here again when I next visit Bratt!

Top guest favorite

Home in Leyden

5 out of 5 average rating, 15 reviews

Mountaintop Views, close to private schools, golf

JasonRating, 5 stars1 week ago

Beautiful property! Fantastic deck and views, and spacious and modern inside. Great place for a weekend with friends!

Top guest favorite

Guesthouse in Dummerston

5 out of 5 average rating, 16 reviews

Cottage amongst the trees

MattRating, 5 stars2 weeks ago

John& Aisha’s cottage was the perfect place for our weekend getaway. Conveniently located between Putney and Brattleboro made it easy to get around. The cottage was very clean and well stocked. John and Aisha were super hosts and went above and beyond with local recommendations to activities we could do. Would highly recommend to anyone traveling through VT.

Top guest favorite

Apartment in Brattleboro

4.97 out of 5 average rating, 78 reviews

Bright and Modern Chestnut Street Apartment

ElizaRating, 5 stars2 days ago

Lucia’s apartment is so cute and quiet. The bed was very comfortable. Clean and beautifully maintained. Would stay again!

Guest favorite

Cabin in West Brattleboro

4.94 out of 5 average rating, 17 reviews

Hidden Forest Cabin: Kitchen, Deck, Babbling Brook

AmyRating, 5 stars3 weeks ago

The house is wonderful - beautiful setting, clean and comfy. Everything you need to enjoy a get away. A short drive to Brattleboro which has plenty of restaurants and stores to enjoy. Theresa and Megan were great hosts. They were very responsive and provided easy to follow instructions plus recommendations of places to eat and explore. Our highlight was breakfast on the deck looking out onto the brook. A very peaceful and beautiful setting. We hope to return.

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Vacation rentals in Guilford

Top-rated vacation rentals in Guilford

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