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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Guest favorite

Guesthouse in Reading

5 out of 5 average rating, 22 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

Guesthouse in Hartland

4.96 out of 5 average rating, 173 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

Guesthouse in Norwich

4.94 out of 5 average rating, 201 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

Guesthouse in Woodstock

4.98 out of 5 average rating, 231 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. ZERO CONTACT WITH OWNERS.

Guest favorite

Guesthouse in Royalton

4.94 out of 5 average rating, 18 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

Guesthouse in Springfield

4.86 out of 5 average rating, 349 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 Lebanon

4.93 out of 5 average rating, 76 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. With high ceilings and a newly renovated interior, you will feel right at home. The room has a new full-sized bed, a bathroom/shower, a kitchenette with coffee maker, electric kettle, microwave, toaster, and compact fridge. A short walk away from restaurants and cafes, and 12-minute drive to Dartmouth College.

Guest favorite

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

Guesthouse in Chester

4.92 out of 5 average rating, 169 reviews

Chester Carriage House-Historic-20 Min to Okemo

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!

Guest favorite

Guesthouse in Norwich

4.9 out of 5 average rating, 30 reviews

Dartmouth Area River House

"Charming Two-Bedroom Apartment on the Ompompanoosuc River in Norwich, VT Inviting two-bedroom private apartment in an 1830s farmhouse. Just a short ten-minute drive from Dartmouth College, it provides a tranquil retreat. Key Features: Ideal for Dartmouth College alumni, parents, and community members due to its close proximity to the campus. Long-Term Rentals: Enjoy a discount for rentals exceeding two weeks, making it a perfect option for extended stays. Two Queen Beds .

Guest favorite

Guesthouse in Cavendish

4.95 out of 5 average rating, 128 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!

Guest favorite

Guesthouse in Hartland

4.95 out of 5 average rating, 956 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 atleast 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 available May - October