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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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor County vacation rentals
Other great vacation rentals in Windsor County
Guest favorite
Guest suite in Hartford
4.91 out of 5 average rating, 317 reviewsSunny Side Airbnb (dog friendly)
Jul 15 – 22
$100 per night
Guest favorite
Guesthouse in Springfield
4.86 out of 5 average rating, 321 reviewsConnecticut River-Cozy Cottage
Jan 21 – 28
$80 per night
Superhost
Condo in Ludlow
4.92 out of 5 average rating, 122 reviewsAll Season Lovely and Zen Okemo Mt Lodge Condo
May 22 – 29
$81 per night
Guest favorite
Guest suite in Royalton
4.96 out of 5 average rating, 180 reviewsPrivate Guest Suite on 155 Acre Royalton Town Farm
Jun 22 – 29
$102 per night
Guest favorite
Cabin in Randolph
4.95 out of 5 average rating, 192 reviewsSecluded Log Home on 109 Acre Natural Wonderland!
Aug 6 – 13
$127 per night
Guest favorite
Guest suite in West Windsor
4.9 out of 5 average rating, 103 reviewsNewly renovated private space on Ascutney Trails
Oct 4 – 11
$95 per night
Guest favorite
Home in Bethel
4.84 out of 5 average rating, 129 reviewsHike, run, swim or cycle in beautiful Central VT
Nov 8 – 15
$108 per night
Guest favorite
Apartment in Tunbridge
4.92 out of 5 average rating, 219 reviewsFairview
Dec 4 – 11
$79 per night
Destinations to explore
- Rentals with a fireplace Windsor County
- Waterfront rentals Windsor County
- Family-friendly rentals Windsor County
- Rentals with a washer and dryer Windsor County
- Rentals with a kayak Windsor County
- Tiny house rentals Windsor County
- Rentals with a fire pit Windsor County
- Guesthouse rentals Windsor County
- Fitness-friendly rentals Windsor County
- Private suite rentals Windsor County
- Rentals with breakfast Windsor County
- Beachfront rentals Windsor County
- Rentals with lake access Windsor County
- Rentals with a sauna Windsor County
- Rentals with pools Windsor County
- Rentals with an accessible height bed Windsor County
- Chalet rentals Windsor County
- Rentals with a hot tub Windsor County
- Townhouse rentals Windsor County
- Condo rentals Windsor County
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- Farmstay rentals Windsor County
- Rentals with beach access Windsor County
- Kid-friendly rentals Windsor County
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- Cottage rentals Windsor County
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- Villa rentals Windsor County
- Rentals with an accessible height toilet Windsor County
- House rentals Windsor County
- Bed and breakfasts Windsor County
- Rentals with a patio Windsor County
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