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Holiday rentals in Windsor County
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Windsor County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor County holiday rentals
Other great holiday rentals in Windsor County
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Guest favourite
Tiny home in Hartland
4.96 out of 5 average rating, 160 reviewsCabin on the Hill
![](https://a0.muscache.com/im/pictures/miso/Hosting-50380789/original/607aae83-3b94-496b-8387-fe8f6c2c81c4.jpeg?im_w=720)
Guest favourite
Tiny home in Hartland
4.94 out of 5 average rating, 264 reviewsPrivate Modern Cabin w/View of Fields, Hills
![](https://a0.muscache.com/im/pictures/0fe67d31-1930-4fe8-93cd-77f2e5a8b13b.jpg?im_w=720)
Guest favourite
Apartment in Bridgewater
4.9 out of 5 average rating, 115 reviewsSouthgate Healing
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Guest favourite
Apartment in Ludlow
4.99 out of 5 average rating, 102 reviewsUpdated Main St Condo in downtown Ludlow!
![](https://a0.muscache.com/im/pictures/5532eb08-56a2-46f2-9eef-b05cd8b507f0.jpg?im_w=720)
Guest favourite
Home in Woodstock
5 out of 5 average rating, 115 reviewsBeautiful Woodstock Home-Perfect for entertaining
![](https://a0.muscache.com/im/pictures/3862e146-9e75-425a-9573-d22dd58e276c.jpg?im_w=720)
Superhost
Apartment in Ludlow
4.82 out of 5 average rating, 106 reviewsOkemo Clock Tower Base Ski-in/Ski-out Condo
![](https://a0.muscache.com/im/pictures/miso/Hosting-53081234/original/93b195a6-17d1-4a54-add1-950f1861422f.jpeg?im_w=720)
Guest favourite
Rental unit in Claremont
4.89 out of 5 average rating, 115 reviewsBeautiful 1 bedroom apartment with balcony
![](https://a0.muscache.com/im/pictures/miso/Hosting-51933644/original/a75984d3-6924-4a99-a1a7-ec064019d301.jpeg?im_w=720)
Guest favourite
Guest suite in Bethel
4.97 out of 5 average rating, 146 reviewsTwo bedroom. Separate enterence.
Destinations to explore
- Rentals with a washing machine and dryer Windsor County
- Rentals with beach access Windsor County
- Rentals with an EV charger Windsor County
- Beachfront rentals Windsor County
- Bed and breakfasts Windsor County
- Rentals with an accessible-height toilet Windsor County
- Rentals with a fireplace Windsor County
- Rentals with a hot tub Windsor County
- Rentals with lake access Windsor County
- Rentals with outdoor seating Windsor County
- Family-friendly rentals Windsor County
- Cottage rentals Windsor County
- Rentals with a firepit Windsor County
- Rentals with breakfast Windsor County
- Apartment rentals Windsor County
- Guest house rentals Windsor County
- House rentals Windsor County
- Private suite rentals Windsor County
- Pet-friendly rentals Windsor County
- Rentals with a kayak Windsor County
- Rentals with a sauna Windsor County
- Cabin rentals Windsor County
- Chalet rentals Windsor County
- Farm stay rentals Windsor County
- Rentals with a patio Windsor County
- Family-friendly rentals Windsor County
- Rentals with pools Windsor County
- Waterfront rentals Windsor County
- Flat rentals Windsor County
- Ski-in/ski-out rentals Windsor County
- Tiny house rentals Windsor County
- Townhouse rentals Windsor County
- Villa rentals Windsor County
- Fitness-friendly rentals Windsor County
- Monthly Rentals Windsor County
- Rentals with an accessible-height bed Windsor County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom