Holiday rentals with outdoor seating in Guilford

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Guilford

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Top Guest favourite
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
4.94 out of 5 average rating, 135 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

Top Guest favourite
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
4.94 out of 5 average rating, 113 reviews

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Top Guest favourite
Home in Guilford
4.96 out of 5 average rating, 140 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 favourite
Campervan/RV in Guilford
4.94 out of 5 average rating, 197 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).

Top Guest favourite
The bright studio features a cozy sleeping area with a spacious bed, a comfortable yellow armchair, and two plush couches. A coffee table sits in the center, with large windows allowing natural light and views of greenery. A television is mounted on the wall.
Apartment in Shelburne Falls
4.97 out of 5 average rating, 618 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Guest favourite
A comfortable white sofa with decorative pillows is positioned against a light wall. A small, light-colored side table holds a potted plant. Natural light streams in through a nearby window, illuminating the wooden floor and a blue woven rug beneath.
Apartment in Dummerston
4.95 out of 5 average rating, 255 reviews

HeART Barn Retreat

Peaceful, romantic retreat in this stunningly large and magical barn. This 1850's historic remodeled barn apartment is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour 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
4.91 out of 5 average rating, 577 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.

Top Guest favourite
A spacious sleeping area is highlighted by large windows dressed in soft curtains, allowing natural light to fill the room. The bed features a checkered blanket with decorative pillows, paired with a simple side table and a small plant, enhancing the cozy ambiance.
Apartment in Brattleboro
4.98 out of 5 average rating, 150 reviews

Bright and Modern Chestnut Street Apartment

Enjoy a unique stay at this central, beautifully-remodeled apartment in quaint Brattleboro, Vermont. The apartment is attached to the back of the charming 1914 home where I live, and has a private, separate entrance so guests can come or go as they please. This carefully-curated apartment includes tasteful decor, a well-appointed kitchenette, organic cotton sheets, and natural bath products. Just off Hwy 91, the apartment is located in the quiet, historic neighborhood of Esteyville.

Top Guest favourite
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, 178 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 favourite
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, 614 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 favourite
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, 571 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 favourite
Guest suite in Guilford
4.96 out of 5 average rating, 191 reviews

Private, Quiet Vermont Studio With Mountain Views

Formerly a musician's retreat, 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. Skiing, skating, sledding and hiking all within a short drive. The town of Brattleboro with lots of shops and restaurants is twenty minutes away

Popular amenities for Guilford outdoor seating rentals