Holiday houses in Guilford

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Top-rated holiday rentals in Guilford

Guests agree: these stays are highly rated for location, cleanliness and more.

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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
4.95 out of 5 average rating, 148 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
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, 142 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 cozy tiny cabin, constructed with wooden beams and a sloped roof, is situated among tall trees. The porch features a railing, inviting seating, and a lantern. Sunlight filters through the foliage, casting a soft glow on the forest floor covered in pine needles.
Treehouse in Brookline
4.98 out of 5 average rating, 269 reviews

Glamping Cabin with Hot Tub on Flower Farm

<b>Vermont's Most Wish Listed</b> ﹏﹏﹏ Nestled in a wooded grove on Tanglebloom Flower Farm, this unforgettable glamping-inspired farm stay invites you to escape the everyday & immerse yourself in nature - comfortably. Designed with a clear roof looking up to the trees and screened sides to let in the breeze, the handmade tiny cabin invites you to slow down. Explore southern Vermont's hikes, farmer's markets & swimming holes or stay put. Perfect for a romantic couples retreat or solo getaway.

Top Guest favourite
A spacious living area features modern seating arrangements with natural light streaming through large glass windows. A small table is set by the window, overlooking the garden. Polished wooden floors and decorative items add warmth to the inviting atmosphere.
Guesthouse in Marlboro
4.97 out of 5 average rating, 185 reviews

Refined, serene and like no other, Marlboro, VT.

Our elegant, supremely comfortable, and private guesthouse is surrounded by a wonderful garden and 350 acres of woodland in the quiet of rural Vermont. We are 30 minutes from Brattleboro to the east, with its many shops and restaurants, and 12 minutes from the small town of Wilmington to our west, with some restaurants, shops, and a supermarket However, we always recommend bringing groceries, etc., for your first night and next morning. We are pleased to offer a 20% discount for 7 days or more!

Guest favourite
Home in Guilford
4.97 out of 5 average rating, 149 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
The cottage exterior features a wooden facade with a green metal roof, framed by vibrant trees. A covered porch with potted flowers welcomes visitors, while large windows allow natural light to fill the space. The peaceful setting highlights the connection to nature.
Cabin in Guilford
4.96 out of 5 average rating, 135 reviews

Guilford Grove Cottage

Guilford Grove Cottage is a simple, comfortable small cottage on the threshold of the forest. A quiet and clean refuge with everything you need to relax in scenic southern Vermont. Prepare meals in the kitchen (breakfast supplies provided), relax on the loveseat, chill on the covered porch and enjoy being on the edge of nature; shoe-free and free from chemicals and artificial fragrances. Brand new construction. Easy access from I-91 & Route 2, 15 mins from Brattleboro and 20 to Greenfield, MA

Top Guest favourite
Tiny home in Wilmington
4.99 out of 5 average rating, 392 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
Treehouse in Guilford
4.99 out of 5 average rating, 197 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 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, 589 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, 316 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, 202 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.

Guest favourite
Yurt in Dover
4.92 out of 5 average rating, 123 reviews

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Seven minutes from the Mount Snow lifts, this creekside yurt turns mountain days into sauna nights. Ski, hike or explore Southern Vermont, then soak in the private hot tub, heat up the cedar sauna and settle in by the wood stove. The soaring dome, pool table, PS5, stocked kitchen and pet-friendly setup make it an easy year-round base for couples, families and friends.

Popular amenities for Guilford holiday rentals

Frequently Asked Questions

  • What are the best places to stay in Guilford?

    Guests regularly choose rentals near the village center or in rural settings with scenic views and access to nature. Larger homes, cabins, and restored farmhouses are often suggested for immersive experiences.

  • What are the best things to do in Guilford with kids?

    Families often enjoy outdoor activities like nature walks, picnicking, or exploring Sweet Pond State Park. Seasonal farm visits, hands-on art workshops, and visits to local markets are also popular with children.

  • What are some of the best things to do in Guilford?

    Wander through Sweet Pond State Park for hiking or paddling, explore local farms, or visit art galleries in the area. Many enjoy attending seasonal community events and markets that reflect Guilford’s rural character.

  • How is the weather in Guilford?

    Guilford experiences cold winters with temperatures around 13–32°F (-11–0°C) and snowy conditions, while summers are warm, ranging from 57–81°F (14–27°C) with occasional rain. Spring and autumn bring changing leaves and mild temperatures.

  • When is the best time to visit Guilford?

    Late spring and early autumn are frequently suggested for milder weather, vibrant foliage, and community events. Summer invites outdoor activities, while winter has a quieter charm for those who enjoy snow-covered landscapes.

  • What are the best places to visit in Guilford?

    Sweet Pond State Park is often recommended for outdoor enthusiasts, and nearby heritage sites share Guilford’s local history. Art galleries and community spaces add variety to a visit year-round.

  • What are some hiking trails in Guilford?

    Explore locally managed forest paths, woodland trails, and routes with views of streams and meadows throughout Guilford. The area around Sweet Pond State Park is often recommended for leisurely hikes and bird watching.

  • What are some family activities we can do in Guilford?

    Discover hands-on farm visits, riverside walks, and swimming or paddling at Sweet Pond State Park. Participating in local craft or music events can be a memorable way for families to connect with the community.

  • What are some of the best day trip ideas from Guilford?

    Plan a day around exploring small towns with historic centers, art studios, or farm stands near Guilford. Popular options include discovering covered bridges, local museums, or the natural scenery of Vermont’s southern Green Mountains.

  • Are there any pet friendly accommodations available in Guilford?

    Many vacation rentals in Guilford welcome pets, especially rural cabins and homes with outdoor space. Guests often find nearby trails and parks convenient for exploring with their dogs.

  • What are some local tips for visiting Guilford?

    Explore outdoor spaces early in the day and check local calendars for community events or farmers markets. Respect rural road etiquette, and consider visiting during foliage season or spring for the region’s popular natural scenery.

  • What is Guilford known for?

    Guilford is known for its rural landscapes, vibrant community traditions, and a history that dates back to early Vermont settlement. The town is recognized for outdoor recreation, working farms, and seasonal gatherings.

  • What are the best hidden gems to explore in Guilford?

    Seek out lesser-known forest paths, quiet ponds, and artist studios tucked among the hills. Heritage sites and small family-run farms often provide a glimpse into the area’s traditions and craftsmanship.

  • What are the best foods to try in Guilford?

    Local cuisine often highlights Vermont cheeses, fresh maple products, and farm-sourced produce. Many visitors seek out apple cider, fresh-baked breads, and dishes featuring seasonal ingredients at area eateries or markets.

  • What should I bring for a trip to Guilford?

    Pack layers for changing temperatures, comfortable shoes for nature walks, and a rain jacket as precipitation is common throughout the year. A camera and reusable water bottle are useful for exploring the countryside and scenic landscapes.

  • What is the nightlife in Guilford like?

    Nightlife in Guilford is relaxed and locally rooted, with small venues, casual gathering spots, and occasional live music around town. Many visitors enjoy quiet evenings under the stars or socializing in welcoming community spaces.

  • What are the most popular events or festivals in Guilford?

    Community gatherings, outdoor concerts in summer, and agricultural fairs are frequently suggested, especially during late spring and fall. The annual Guilford Fair around Labor Day weekend is a local tradition with exhibits, food, and live entertainment.

  • Are there family friendly vacation rentals in Guilford?

    Guilford has a range of family-friendly vacation rentals, including cottages, homes, and farm stays set among the quiet hills. Look for features like kitchens, outdoor spaces, and proximity to parks and family activities.