Vacation rentals in Guilford

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Top-rated vacation rentals in Guilford

Guests agree: these stays 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 West Brattleboro
4.94 out of 5 average rating, 136 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, 124 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!

Guest favourite
An open concept living space features four arched windows that allow ample natural light. Wooden floors complement the revealed post and beam construction. A wooden dining table is centrally placed, with a cozy seating area in a corner, creating a relaxed environment.
Home in Westminster
4.89 out of 5 average rating, 264 reviews

Spacious Loft with View

Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

Guest favourite
Home in Guilford
4.96 out of 5 average rating, 141 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
Tiny homes in Wilmington
4.99 out of 5 average rating, 354 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favourite
Camper/RV in Guilford
4.95 out of 5 average rating, 208 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
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
A charming wooden cabin is nestled among trees, featuring a metal roof and a welcoming porch. Two colorful chairs, one red and one blue, are positioned outside beside a boulder, complemented by flower boxes with blooming plants, creating a serene outdoor space.
Cabin in Newfane
4.99 out of 5 average rating, 177 reviews

Custom cabin by the river in Newfane, VT

OPEN mid-MAY-OCTOBER. Our beautiful one-room custom cabin is on the edge of the woods surrounded by the Rock River. It's freshly appointed, with a king-size bed, is spotlessly clean and very romantic. The cabin has simple cooking facilities (details below) and an outdoor grill, twinkle lights on the deck, hammock, and 2 fire-pits, one by the cabin, and one on the beach. One COMPLIMENTARY BREAKFAST is included, with homemade popovers, fresh out of the oven. A smoke-free property.

Guest favourite
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, 180 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 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
4.97 out of 5 average rating, 577 reviews

Serenity Now - Couples Retreat or Writer's Dream

COUPLES RETREAT or SOLO EXCURSION NEAR BRATTLEBORO 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 ($55.00 value) Ask me about ELOPEMENT & VOW RENEWAL CEREMONIES

Top guest favourite
The exterior of a renovated log cabin is presented, featuring a red metal roof and a charming porch with steps leading up. The cabin is surrounded by lush greenery, with rolling hills visible in the background under a clear blue sky.
Cabin in Newfane
4.99 out of 5 average rating, 308 reviews

Log Cabin: Amazing Views, River Frontage, Hot Tub

A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.

Top guest favourite
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, 191 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 Guilford vacation rentals

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  2. United States
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  4. Windham County
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