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 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

ﺩ.ﺇ737 per night

Guest favorite

Home in Killington

4.92 out of 5 average rating, 165 reviews

Cozy Condo Tucked in the Heart of Killington

Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!

Jun 21 – 28

ﺩ.ﺇ691 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).

Sep 7 – 14

ﺩ.ﺇ703 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

ﺩ.ﺇ2,217 per night

Guest favorite

Home in Hartford

4.96 out of 5 average rating, 102 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

ﺩ.ﺇ1,195 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.

Oct 30 – Nov 6

ﺩ.ﺇ624 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.

Oct 28 – Nov 4

ﺩ.ﺇ365 per night

Guest favorite

Home in Rochester

4.95 out of 5 average rating, 144 reviews

Cottage in the Heart of the Green Mountains

Welcome to quintessential Vermont! Come stay at my cozy yet spacious, rustic yet modern, much-beloved Red Acre Cottage. Red Acre Cottage is nestled on a scenic ridge in the idyllic town of Rochester, just east of the Green Mountains and right off of Vermont Scenic Byway Route 100, one of the state's prettiest roads. Red Acre Cottage is an easy drive to Killington/Pico, Sugarbush, Mad River Glen, Rikert Nordic Center/Blueberry Hill XC skiing, Suicide Six, and Stowe Mountain.

Aug 25 – Sep 1

ﺩ.ﺇ606 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 29 – Dec 6

ﺩ.ﺇ593 per night

Guest favorite

Home in Plainfield

4.89 out of 5 average rating, 119 reviews

Historic Home on 17 acres of land. Go escape!

This place is a dream. Please enjoy the outdoors and everything this amazing place has to offer. The pool opens around May 2024! It is a heated pool and salt water. Pool rules: absolutely no diving. No children under the age of 18 should be near or in the pool area without supervision under any circumstances. NO glassware by the pool. If there is an incident with glass near the pool area please tell our property manager immediately. If you need anything just ask

Nov 5 – 12

ﺩ.ﺇ2,315 per night

Guest favorite

Home in Bethel

4.85 out of 5 average rating, 130 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.

Dec 24 – 31

ﺩ.ﺇ493 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 23 – 30

ﺩ.ﺇ641 per night