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 Mount Holly

4.9 out of 5 average rating, 116 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.

Dec 1 – 8

G$38,576 GYD per night

Guest favorite

Home in Weston

4.95 out of 5 average rating, 227 reviews

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

Sep 13 – 20

G$41,878 GYD per night

Guest favorite

Home in West Windsor

4.98 out of 5 average rating, 163 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).

Mar 7 – 14

G$41,700 GYD per night

Superhost

Home in Quechee

4.83 out of 5 average rating, 127 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.

May 20 – 27

G$29,315 GYD per night

Guest favorite

Home in Tunbridge

4.98 out of 5 average rating, 314 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.

Oct 23 – 30

G$62,459 GYD per night

Guest favorite

Home in Woodstock

5.0 out of 5 average rating, 110 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!

Sep 17 – 24

G$126,227 GYD per night

Guest favorite

Home in Hartford

4.96 out of 5 average rating, 101 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.

Dec 9 – 16

G$68,995 GYD per night

Guest favorite

Home in Barnard

4.92 out of 5 average rating, 141 reviews

Cozy 2bd, Tennis Court, Steps to Lake, on 6 acres

This 2nd floor space is great for small groups and couples. All wood interior space has been newly updated with modern appliances, handmade slab countertops, and cozy furniture. Directly across from Silver Lake and the Barnard General Store, with 6 parklike acres including a tennis court (with pickle ball)! Easy to find, minutes from Woodstock, VT. and award-winning dining, just 3 minutes to Silver Lake State Park, and just a few miles to multiple access points of the Appalachian Trail.

Jan 2 – 9

G$36,454 GYD per night

Guest favorite

Home in Ludlow

4.92 out of 5 average rating, 139 reviews

149 Upper Crossroad Unit A

Renovated in the Summer of 2018, the Townhomes at Clock Tower are a beautiful, spacious year-mountain retreat. It sleeps 8 and has been beautifully appointed, with 2 Family rooms, 3 bedrooms, 2 bathrooms, a large open concept Kitchen, and Dining room with Gas Stove. The kitchen boasts granite countertops, dishwasher, with essentials. A short 5-minute walk to the Okemo Clock Tower Base Lodge, or a weekend/holiday shuttle that stops at the home for those who prefer not to walk it.

Nov 6 – 13

G$20,766 GYD per night

Guest favorite

Home in Rochester

4.97 out of 5 average rating, 182 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!

Nov 11 – 18

G$33,762 GYD per night

Guest favorite

Home in Bethel

4.84 out of 5 average rating, 129 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.

Nov 8 – 15

G$25,968 GYD per night

Guest favorite

Home in Hartford

4.86 out of 5 average rating, 151 reviews

Beautiful Historic 1909 Library with a Fireplace

An intimate experience with history! Quechee’s first Library (1909) original hardwood floors and shelves with treasures. Romantic Gas Fireplace, Claw foot tub (with NO shower) in the bedroom, Living area, Kitchenette, AC, WIFI, Comfy Queen bed, Window Seat, unique art, many amenities. Across the street, Covered Bridge, Waterfall, Simon Pearce Restaurant w/ Glass Blowing. Parker House with WhistlePig whiskey tasting and more. Hope you love it!

Jul 17 – 24

G$36,502 GYD per night