Vacation rentals with outdoor seating in Guilford

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Top-rated outdoor seating 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, 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

A cozy sleeping area is highlighted by wooden walls and a decorative wall tapestry. A spacious bed is adorned with white linens, while a bedside table displays a lamp and a decorative tray. A blooming orchid in a white pot adds a touch of nature near the window.

Apartment in Brattleboro

4.8 out of 5 average rating, 118 reviews

Beautiful Artsy Studio w/Fireplace - Pet-Friendly!

Welcome to the Artsy Studio at Culbertson House, a unique studio apartment with historic charm in a beautiful setting. The place features a big, romantic stone fireplace, wooden floors and walls, tasteful, comfortable furnishings, plentiful art and tasteful, artsy decor, full kitchen, 55" TV, and a deliciously comfortable king-size bed, all in a private yet convenient location. Bring your fuzzy friends with you as we are always pet-friendly! Skiing and ice skating are only five minutes away!

Superhost

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

4.92 out of 5 average rating, 531 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 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, 165 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

An inviting interior space features a cozy seating area with a dark couch and a glass coffee table. Natural light enters from a door leading outside, and a wood stove is prominently positioned next to a dining table, enhancing the rustic feel of the camper.

Camper/RV in Guilford

4.93 out of 5 average rating, 143 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 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, 148 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

A welcoming porch features a decorative swing with two cushions and a small table, creating a serene space. Natural light filters through large windows, and colorful banners hang above, while a wooden structure nestles comfortably in the surrounding greenery.

Cabin in Guilford

4.99 out of 5 average rating, 139 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

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, 587 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, 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.

Guest favorite

An open living room and kitchen area is featured, furnished with a beige sofa, a coffee table, and a television mounted on a wooden stand. The kitchen includes wooden cabinets, a refrigerator, and a small dining space with two stools at the counter.

Apartment in Brattleboro

4.89 out of 5 average rating, 570 reviews

Cozy, Private & Great location for exploring VT !

The apartment is centrally located, cozy, quiet and private. It has been set up to be a comfortable retreat. It's private entrance leads upstairs to an open living room/ kitchen space. The back door opens to a deck overlooking a ball field and green hills. The sleeping nook contains a queen size , metal framed bed. The mattress is comfortable and the sheets are soft. VT charges 10% tax

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, 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, 369 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.