Holiday rentals in Windsor
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Windsor
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor
Guest favourite
Home in Adams
4.9 out of 5 average rating, 91 reviewsMountain View Hideaway
Guest favourite
Rental unit in Shelburne Falls
4.86 out of 5 average rating, 396 reviewsBig, sunny 1893 flat steps from Bridge of Flowers
Superhost
Rental unit in Adams
4.8 out of 5 average rating, 41 reviewsDowntown Studio in Adams
Guest favourite
Rental unit in Lanesborough
4.87 out of 5 average rating, 107 reviewsCozy Rustic Apt. in 18th c. Berkshire Farmhouse
Guest favourite
Home in Ashfield
5 out of 5 average rating, 35 reviewsAn 18th century farmhouse
Guest favourite
Home in Hinsdale
4.93 out of 5 average rating, 56 reviewsBerkshire Lake Retreat
Guest favourite
Guest suite in Dalton
4.98 out of 5 average rating, 64 reviewsBerkshires getaway: nature, culture & relaxation
Guest favourite
Home in Chester
4.96 out of 5 average rating, 335 reviewsRiverfront Getaway
Destinations to explore
- Cambridge Holiday rentals
- New Haven Holiday rentals
- Lake George Holiday rentals
- Providence Holiday rentals
- Catskill Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- Montreal Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Cape Cod Holiday rentals
- 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