Vacation rentals in Windsor County

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Top-rated vacation rentals in Windsor County

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

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Guest favorite

Guesthouse in Hartland

4.96 out of 5 average rating, 176 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

Cottage in Hartland

4.97 out of 5 average rating, 449 reviews

Breeze Hill Cottage

This cozy two bedroom home sits on a rural dirt road overlooking fields, woods, and the NH mountains. Watch birds from the window, relax on the patio, and enjoy the flower gardens. The cottage boasts modern amenities mixed with antiques. Please note: if we don’t respond to an Airbnb message and you need to speak with us, call us on our phones day or night!!! We have had people message us when we were asleep and so we have not been aware and have not responded. Call us! We will hear the phone!

Guest favorite

Guesthouse in Woodstock

4.98 out of 5 average rating, 233 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 Springfield

4.86 out of 5 average rating, 350 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

Barn in Woodstock

5 out of 5 average rating, 232 reviews

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". The loft is a newly built apartment on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a Cathedraled living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony.

Guest favorite

Guest suite in Hartford

4.91 out of 5 average rating, 362 reviews

Sunny Side Airbnb (dog friendly)

Sunny Side Airbnb is located on a secluded 10+ acre property with plenty of outdoor space for dogs to run around and a short hiking trail with views. The Airbnb is located on the farther end of the house with a deck overlooking garden views, a fire pit, and an open field. Convenient location near shops and restaurants. Just over a mile from I-89 off Rt 4 in Quechee, Vt. A short drive to WRJ and W Lebanon, NH, 9.1 miles to Woodstock, VT, 11 miles to Hanover, NH, and 13.4 miles to DHMC.

Guest favorite

Guest suite in West Windsor

4.92 out of 5 average rating, 118 reviews

Newly renovated private space on Ascutney Trails

Newly renovated private space on Ascutney trails--walking distance Ascutney Outdoors Center, hotel, Maple Kitchen Restaurant, skiing, and Brownsville Butcher & Pantry. Trail access in back yard with miles of hiking, mountain biking, running and skiing. Parking for 2 cars. Close to Woodstock shops and Okemo adventure center. Private keycode entrance with self-check in. Microwave, refrigerator, Keurig, coffee and tea provided. Air conditioned during the summer. Television and fast wifi.

Guest favorite

Rental unit in Royalton

4.98 out of 5 average rating, 173 reviews

Quiet Vermont Get Away

This space is ideal for a family or friends. This is a dog-friendly apartment located above our garage with stairs. Just 5 min off Exit 3 on I89. Full kitchen to make family meals. Cozy living/dining space. Come and stay for skiing, snowmobiling, hiking, biking, golf, local breweries and so much more depending on the season. Close to Vt Law School. 35-40 minutes to Killington, Pico, Stowe, Bolton and Sugarbush. 20 minutes to Quechee and Woodstock. Sleeps 5/6 with using a bunk bed.

Guest favorite

Cottage in Windsor

4.97 out of 5 average rating, 366 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Guest favorite

Rental unit in Weathersfield

4.99 out of 5 average rating, 171 reviews

The Loft at Weathersfield

Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

Guest favorite

Home in Bethel

4.85 out of 5 average rating, 145 reviews

Hike, run, swim or cycle in beautiful Central VT

Enjoy the summer in beautiful Vermont. The guest area is the entire main floor of a large house with my quiet second home above. Private entrance, 2 bedrooms, full bathroom with washer and dryer, speedy fiber optic internet. The open kitchen has full sized stove and fridge with good cookware and appliances, adjacent to a large open living area. On a paved scenic road. Go up to Silver Lake for a swim, head out on any of the back roads for a run or a ride.

Guest favorite

Guesthouse in Hartland

4.95 out of 5 average rating, 958 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