House vacation rentals in Windsor County

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Top-rated house rentals in Windsor County

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Guest favorite

Home in Barnard

4.98 out of 5 average rating, 121 reviews

The Looking Glass, a modernistic escape

Welcome to The Looking Glass, a modernistic escape located in Barnard, Vermont! With floor to ceiling, south facing windows, you’ll be relaxing in comfort while taking in breathtaking views of the Green Mountains! You’ll love our commercial grade kitchen, boasting high-end cookware, a Wolf range and Subzero fridge. Take the spiral staircase upstairs to enjoy a long bath before calling it a night in the spacious king bed. Explore Silver Lake & Woodstock! Hike, bike or ski the neighboring trails

Guest favorite

Home in Mount Holly

4.89 out of 5 average rating, 122 reviews

Newly renovated. Minutes to Slopes & Trails

Healdville Hideaway has 3 acres of rural charm located on the backside of Okemo Mountain. Charm is a plenty in this 1500 SF single story, newly renovated home with views of the mountain & fields full of wildlife. This modern country decorated home provides the perfect comfortable setting for single or multi family enjoyment. The fully functional kitchen is available for making a quick snack or a full meal. The back acreage is perfect for building a snowman or doing a little cross country skiing.

Guest favorite

Home in Tunbridge

4.97 out of 5 average rating, 352 reviews

The Barnbrook House

Come relax in the serenity of the quiet countryside. This home boasts beautiful views, a large stone fireplace, and stained glass windows throughout the home. Enjoy the comforts of home with a full kitchen, amenities, and beds with 1500 thread count sheets while exploring the interesting features of this one of a kind house. Sit by the spring fed pond overlooking the property laced with apple trees. The home has direct access to short walking trails and is close to VAST trails for snowmobiling.

Superhost

Home in Quechee

4.81 out of 5 average rating, 135 reviews

Shelly's Place

The home is conveniently located within walking distance to Vins and Simon Pearce yet fully private. 15 min. drive to Dartmouth College / 20 min. drive to Dartmouth Hitchcock Hospital. Home has 2 bedrooms, 1 bath, open living room and includes cable & high speed wifi. A port-a-crib & air mattress and two twin rollaways are available. Enjoy complimentary coffee, tea, farm fresh organic eggs, & other breakfast items. Home is close to the Quechee Gorge as well as about 27 miles from Killington.

Guest favorite

Home in West Windsor

4.98 out of 5 average rating, 185 reviews

Meadow View. 35 acres outside your door!

Meadow View is your pet friendly home away from home. 35 acres at your fingertips including 2 trout ponds and 25 acres of wooded trails (perfect for cross country skiing/snow shoeing in winter!). The unit features new furniture and a full kitchen. Minutes from Mt. Ascutney (trails galore. rope tow in the winter). The unit is perfect spot for couples craving time in rural Vermont or for families/outdoor enthusiasts who want to go mountain biking, skiing, hiking. (Okemo 30 min. Killington 45).

Guest favorite

Home in Woodstock

5 out of 5 average rating, 125 reviews

Beautiful Woodstock Home-Perfect for entertaining

Newly renovated - 4 bedroom, 3 bath house, perfect for relaxing or entertaining. Close to all that the Woodstock Village and the Upper Valley has to offer. Amazing location! Only 1.5 mi to the Woodstock Green. Explore the property and feast on the blackberries in summer, raid the tomato garden in the late summer/early fall, and pick the wild fall apples for munching or baking. Bring your snowshoes or cross country skis (in winter) or hiking shoes in summer and explore the property and beyond!

Guest favorite

Home in Hartford

4.96 out of 5 average rating, 107 reviews

Meadow Vista: 4BR Home w/ Sweeping Quechee Views

From its perch on a hilltop high above the scenic Quechee Valley, "Meadow Vista" strikes a perfect balance between cul-de-sac privacy and the convenience of a location less than a mile from the four-season amenities of the Quechee Club. You'll wake up every morning to breathtaking 180-degree views from a modern kitchen, dining room, living room, and upstairs bedrooms. Typically available from October through mid-May. this is one of the most spectacular rental properties Quechee has to offer.

Superhost

Home in South Londonderry

4.84 out of 5 average rating, 128 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

This VERY NEW and VERY romantic treehouse is finished!!! The Honey Pond Treehouse is made especially for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…You will enjoy private hot tubbing, sauna time, relaxing, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes…biking & disc golf at Magic Mnt!

Guest favorite

Home in Rochester

4.97 out of 5 average rating, 195 reviews

The Guest House at Sky Hollow

This quiet hilltop house on an 1800's farm turned homestead at the end of a dirt road offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Guest favorite

Home in Plymouth

4.95 out of 5 average rating, 236 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Welcome to one of the most unique "retreats" in Vermont! Located on top of a private mountain, beautiful 100 mile views of the White Mountains. Ideally located between Killington (7 miles) and Okemo resorts, near Woodstock and Long Trail Brewery. Relax in the Jacuzzi hot tub while enjoying the views and stars. Private hiking trails, waterfalls, with trail maps! 7 miles to the beach at Camp Plymouth State Park. Secluded yet close to everything. New ventilation system.

Guest favorite

Home in Bethel

4.85 out of 5 average rating, 144 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.

Superhost

Home in Killington

4.84 out of 5 average rating, 101 reviews

Bear Creek Lodge

This ski chalet just off the Killington Access Road features exposed-beam vaulted ceilings and a wrap-around porch. Enjoy the peaceful running creek along the back of the property. Inside, you'll have a cozy mountain atmosphere plus an extensive collection of board games and DVDs for those rainy days or for warming up after a day in the snow. Full kitchen for group meals and plenty of parking. Close to the slopes, restaurants, and all the area attractions!