Vacation rentals in Windsor County
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Windsor County
Guests agree: these stays are highly rated for location, cleanliness, and more.
Cottage in Hartland
4.97 out of 5 average rating, 417 reviewsBreeze 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!
Apr 13 – 20
Guesthouse in Woodstock
4.98 out of 5 average rating, 203 reviewsCozy 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.
Nov 2 – 9
Guest suite in Royalton
4.95 out of 5 average rating, 175 reviewsPrivate Guest Suite on 155 Acre Royalton Town Farm
1 Bed, 1 Bath apartment attached to historic farm house. This cozy space is the perfect spot for a weekend getaway or a long family vacation on a historic Vermont Farm. Equipped with all the linens and dishes you will need and even a few extras like farm fresh eggs in the fridge and hot chocolate. Close to I-89 and 30 minutes of Ski Resorts like Saskadena Six. Property of 155 acres has trails, sledding hills and our farm animals you can enjoy. Check our reviews, you won't be disappointed!
Apr 11 – 18
Vacation rentals for every style
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Popular amenities for Windsor County vacation rentals
Other great vacation rentals in Windsor County
Guesthouse in Vershire
4.93 out of 5 average rating, 241 reviewsThe Peaceable Kingdom
Oct 29 – Nov 5
Apartment in Rutland
4.96 out of 5 average rating, 514 reviewsYour home away from home
Nov 26 – Dec 3
Condo in Killington
4.81 out of 5 average rating, 225 reviewsCome to Killington this Winter!
Apr 19 – 26
Tiny home in Hartland
4.94 out of 5 average rating, 251 reviewsPrivate Modern Cabin w/View of Fields, Hills
Jan 25 – Feb 1
Apartment in Claremont
4.88 out of 5 average rating, 108 reviewsBeautiful 1 bedroom apartment with balcony
Oct 14 – 21
Condo in Killington
4.92 out of 5 average rating, 143 reviewsRenovated, w/Covered Parking-Shuttle-Walk to Lifts
May 26 – Jun 2
Condo in Ludlow
4.92 out of 5 average rating, 117 reviewsAll Season Lovely and Zen Okemo Mt Lodge Condo
May 21 – 28
Guest suite in Shrewsbury
4.91 out of 5 average rating, 258 reviewsValley View
May 19 – 26
Guesthouse in Hartland
4.95 out of 5 average rating, 910 reviewsYurt In The Woods - Private Refuge
Jan 3 – 10
Apartment in Hartland
4.87 out of 5 average rating, 437 reviewsSunny Studio Apartment in Hartland
Aug 28 – Sep 4
Barn in Woodstock
5.0 out of 5 average rating, 200 reviewsTHE LOFT, stunning views from a timber framed barn
Sep 16 – 23
Guesthouse in Springfield
4.86 out of 5 average rating, 321 reviewsConnecticut River-Cozy Cottage
Dec 1 – 8
Destinations to explore
- Chalet rentals Windsor County
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