Guesthouse vacation rentals in Windsor County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Windsor County

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

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Guest favorite

A charming cottage is set against a backdrop of lush trees, with a deck extending from the front. The warm, orange sky creates a serene atmosphere, casting soft light on the exterior of the house and surrounding landscape.

Guesthouse in Hartland

4.96 out of 5 average rating, 189 reviews

Cottage for Two/Solo Getaway/Musician's Retreat

Luxurious, well appointed cottage with beautiful sunrise view located between Woodstock VT and Hanover NH. An inspiring treat for musician’s getaway is a fully restored 1929 Steinway L. Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer and very comfortable queen bed. A romantic getaway in the woods, a place to relax, work in peace, or explore the beauty and history of the area. Hiking, biking, fly fishing, hot air balloon rides and shopping are all close by.

Guest favorite

A charming log cabin is nestled among lush greenery, featuring a classic A-frame roof and front porch adorned with decorative lights. Potted plants enhance the entrance, contributing to the warm and inviting exterior. The tranquil setting is surrounded by trees, creating a peaceful atmosphere.

Guesthouse in Norwich

4.93 out of 5 average rating, 217 reviews

Vermont Log Guest Home-Close to Dartmouth

Beautiful log guest home in Norwich, VT available for Dartmouth events or other local happenings features 1 bedroom (queen), loft (queen & futon) on second floor & 1 bathroom on first floor. Can sleep 6. Completely detached from main home. Located minutes from town in a private wooded property. Cozy up to the indoor fireplace or explore the local area. Many trails close by. Excellent location only 10 minutes to Dartmouth or 5 minutes to King Arthur Flour. Close to Quechee and Woodstock.

Guest favorite

A serene view of a spring-fed pond reflects the soft colors of sunset, with gentle ripples on the water's surface. Lush greenery surrounds the pond, and distant hills rise along the horizon under a cloudy sky.

Guesthouse in Royalton

4.93 out of 5 average rating, 30 reviews

2 bdrm VT Farmhouse w/ Pond

Our guest unit is a mix of rustic 1890s farmhouse and cozy mountain retreat, providing comfort and convenience to unplug and enjoy the outdoors or to work remotely - with high speed wifi and a view! The space has a private entrance, front porch, 2 upstairs bedrooms, well appointed kitchenette, large living room (can add an air mattress) and two desks/workspaces. Our 67 acre wooded property offers reliably incredible sunsets and star gazing, trails for hiking, and a spring-fed pond for dips.

Superhost

An aerial view captures a cozy cottage situated along the Connecticut River. Lush greenery borders the water, and a small pathway leads to the cottage. A boat glides along the river, highlighting the serene setting surrounded by forests and rolling hills.

Guesthouse in Springfield

4.84 out of 5 average rating, 380 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

Guest favorite

Guesthouse in Chester

4.92 out of 5 average rating, 183 reviews

Historic Carriage House-20 Min to Okemo-Magic MTN

Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, yoga studio and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers + breweries. Close proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington) Come experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!

Top guest favorite

A cozy room features a full-sized bed covered with a white blanket and accent pillows. A kitchenette with cabinetry, coffee maker, and compact fridge is visible. A framed landscape print adorns the wall, with natural light coming through windows beside the bed.

Guesthouse in Lebanon

4.95 out of 5 average rating, 128 reviews

Private guesthouse in Lebanon

This cozy one-room guesthouse is located on a quiet street off the green in downtown Lebanon, NH. It offers a private entrance with access to a lovely outdoor patio and gas grill. The room has high ceilings, a full-sized bed, a bathroom/shower, and a kitchenette with coffee maker, electric kettle, microwave, toaster, and compact fridge. A short walk away from restaurants and cafes and a 12-minute drive to Dartmouth College. Please note that there is no kitchen sink or stove.

Top guest favorite

A cozy sleeping area is featured with a spacious bed adorned with soft pillows. Natural light filters through sheer curtains, illuminating warm wooden walls. A small TV and a decorative chair provide additional comfort, while a touch of greenery enhances the inviting atmosphere.

Guesthouse in Randolph

4.96 out of 5 average rating, 261 reviews

Macintosh Hill Farm

Originally built in 1817 by the Macintosh Family, our family farm is steeped in historical beauty. Nestled in the hills of Bethel, we live in an area rich with skilled farmers, shepherds, cheese makers, and artists. We make apple cider from our orchard, raise chickens, make maple syrup, and grow produce for our family. Our home is surrounded by far reaching views, big skies and lush countryside. Each booking gets privacy & exclusivity, making our farm your perfect retreat.

Guest favorite

The spacious interior of the yurt features a circular design with natural wood and fabric elements. Comfortable seating areas include a queen-sized futon and a wooden sofa. Large windows allow natural light to fill the space, while a wood stove provides warmth.

Guesthouse in Hartland

4.95 out of 5 average rating, 1,005 reviews

Yurt In The Woods - Private Refuge

The Yurt In The Woods is 30 ft in diameter which offers 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for all Weekends. I require at least a two night stay for the whole month of October. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October

Top guest favorite

A cozy cabin is nestled among the trees, showcasing a rustic wooden exterior with large windows. It overlooks a gentle slope covered in green grass and wild plants, with sunlight filtering through the canopy above, creating a serene and inviting atmosphere.

Guesthouse in Woodstock

4.98 out of 5 average rating, 255 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

Guest favorite

The inviting bedroom features a queen-sized bed adorned with a colorful floral-patterned blanket. A gray sofa adds comfort alongside a small lamp and nightstand. Soft light fills the room, highlighting the vibrant green walls and decorative wall accents.

Guesthouse in Hartford

4.87 out of 5 average rating, 127 reviews

Addie's Place

A cozy and quiet space close to Dartmouth College (8 mins), Dartmouth Hitchcock Hospital (12 mins), and White River Junction Center (5 mins). You will have a private entrance to the space and access to a yard, a 3 season patio room, bedroom with a queen sized bed and queen pullout couch, a separate dining area, grill, and a private bathroom. There is no kitchen but there is a mini fridge, table, coffee/tea bar, plates, utensils, mugs, and a microwave.

Top guest favorite

A spacious living area features a large, yellow sofa paired with a circular coffee table. Two comfortable chairs in rust color are positioned nearby. A vintage-style stove is present against the wall, with soft lighting provided by wall sconces. A door leads to another room.

Guesthouse in Cavendish

4.96 out of 5 average rating, 165 reviews

Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!

Cavendish Cottage Guest House — With Sauna Access! Freshly renovated with designer touches, this charming guest house blends style, comfort, and Vermont charm. Starting mid-September 2025, enjoy free access to our traditional sauna — shared with two other units and your host. Plush robes provided so you can unwind after skiing or hiking, then cozy up by the pellet stove. 10 minutes to Okemo, 2 minutes to groceries, and super comfy vibe await!

Top guest favorite

A comfortable living room is presented, featuring two patterned armchairs and a dark sofa. A coffee table occupies the center space, with side tables and lamps positioned strategically. Natural light filters through the windows, while a ceiling fan offers a cooling breeze.

Guesthouse in Plymouth

4.97 out of 5 average rating, 106 reviews

Quiet Couples Retreat near Killington and Okemo

Clean and comfortable rural guest house in quiet and serene setting on 68 acres of land in Plymouth on Vermont Route 100, a top 10 scenic road in the US. Only 15 minutes from Killington and Okemo and minutes from hiking, lakes, fishing, boating, swimming, and a state beach and boat landing. Historic Woodstock is 15 miles away. Guests must be 21+. Inquiries from guests with no prior reviews on Airbnb will be further screened.