Guesthouse vacation rentals in Windsor County

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Top-rated guesthouse rentals in Windsor County

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

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Top guest favorite

The kitchen features a combination of modern stainless-steel appliances and dark cabinetry with granite countertops. An oversized skylight above allows natural light to fill the space. A light wood floor complements the room, and a woven rug adds a warm touch beneath the fixtures.

Guesthouse in Reading

5 out of 5 average rating, 30 reviews

Peace & quiet at Comet Farm

Get your second wind at Comet Farm. Nestled amid rolling hills and sprawling meadows, this retreat sits between Woodstock and Okemo Mountain, a setting for hiking, cycling, skiing, family outings and moments of self-discovery. As the sun bathes the landscape in warm hues, the expanse of big skies will leave you awe-inspired throughout the day, while the night unveils a breathtaking canvas of bright stars. Awaiting you are Vermont experiences such as antique stores, farmers markets and breweries.

Guest favorite

A panoramic view of a winding river surrounded by vibrant autumn foliage. Trees in shades of green, orange, and yellow line the banks, creating a picturesque natural landscape under a cloudy sky. The river flows calmly through rocky terrain, inviting exploration and appreciation of the surrounding beauty.

Guesthouse in Hartland

4.96 out of 5 average rating, 180 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 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

4.92 out of 5 average rating, 25 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.

Guest favorite

A private boat is seen docked at a wooden pier, surrounded by lush greenery. The calm river reflects the surrounding trees, creating a serene scene. Light filters through the foliage, enhancing the peaceful atmosphere of the waterfront.

Guesthouse in Springfield

4.85 out of 5 average rating, 373 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.

Top guest favorite

The exterior of the guesthouse features rustic wooden siding, adorned with multiple windows that provide natural light. A flower garden blooms in vibrant colors, set against a backdrop of lush greenery and trees, creating an inviting entrance to the studio.

Guesthouse in Mount Holly

4.95 out of 5 average rating, 66 reviews

Moon Acre Farm Green Mountain Oasis - near Okemo

Relax in the mountain stillness, overlooking a pond in a stylish studio guesthouse at Moon Acre Farm. Our guesthouse is off of the main roads, surrounded by 60,000 acres of National Forest, yet 15 miles drive to restaurants, shopping, and boating. The studio is open and spacious (900 sqft), and artistically built into the upper level of our barn to take advantage of the views of the mountains and pond. Enjoy sitting on the balcony overlooking a stream or explore the gardens and woods.

Guest favorite

A serene outdoor scene captures a lush green landscape with a pond in the foreground. Tall grass gently sways in the breeze while trees provide a natural backdrop. A charming house is visible in the distance, nestled among the foliage under a cloudy sky.

Guesthouse in Pomfret

5 out of 5 average rating, 22 reviews

Cozy, clean studio with picturesque Vermont views!

Lovely studio in the heart of the mountains! Our cozy and well-lit space is perfect for solo travelers or couples looking to explore all that Vermont has to offer. Enjoy a queen-sized bed, pull out sofa, kitchenette and a charming bathroom. 2 miles to the Woodstock Village and 1 mile to Saskadena Six (formerly Suicide 6). Experience local life with all the modern amenities you need for a memorable stay. ***In the winter months, 4 wheel drive or all wheel drive is mandatory.***

Guest favorite

The entrance to the Carriage House is framed by a vibrant red door and a side panel featuring a small square window. A bright yellow mum plant and a pumpkin are placed on a stone pathway leading to the door.

Guesthouse in Chester

4.92 out of 5 average rating, 178 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 stone path leads to the private entrance of the guesthouse, bordered by gravel and flower pots. A small outdoor seating area is visible, featuring a table and chairs, with a wooden fence providing privacy.

Guesthouse in Lebanon

4.95 out of 5 average rating, 114 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

An outdoor hot tub is illuminated with subtle red lights, inviting relaxation. The backdrop features a panoramic view of rolling hills and mountains under a twilight sky, showcasing the lush greenery of the surrounding landscape.

Guesthouse in Randolph

4.96 out of 5 average rating, 259 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.

Top guest favorite

The bathroom features a charming claw foot bathtub with a shower attachment. Natural light floods the space through a large window that overlooks a lush green landscape. Shelving holds essential toiletries, while soft cotton towels are easily accessible nearby.

Guesthouse in Hartland

4.95 out of 5 average rating, 991 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 $40 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

Guest favorite

A wooden deck extends from the guest house, surrounded by tall trees and lush greenery. Sunlight filters through the leaves, casting dappled shadows on the floor. A gentle stream can be seen flowing nearby, adding to the tranquil ambiance of the setting.

Guesthouse in Woodstock

4.98 out of 5 average rating, 242 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

Guesthouse in Cavendish

4.95 out of 5 average rating, 151 reviews

Cozy Cavendish Bunkhouse

Enjoy a stylish & relaxing experience at this centrally-located guest home. Newly renovated with local interior designer! The bunkhouse is behind our main house. We're a quick 10 minute drive to Okemo Ski Resort! You can enjoy plenty of nature, hiking, snowmobiling, mountain biking, skiing/snowboarding and much more in the area! Follow the Bunk House on IG where we’ll share all the local happenings!! ‘at’cozycavendishbunk We look forward to hosting you!