Search Cottages in Windsor
Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Cottages in Windsor
Compare 50 Cottages in Windsor with updated reviews, rates, and availability.
Charming historic cottage on scenic road to Mt. Greylock
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (101)
Cozy Berkshire cottage with fireplace.
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (21)
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
6.0 out of 10, (1)
Charlemont Retreat on Chickley River w/ EV Charger
Charlemont Retreat on Chickley River w/ EV Charger
10.0 out of 10, Exceptional, (1)
Cottage in the Clouds With Mountain Views
Cottage in the Clouds With Mountain Views
9.4 out of 10, Exceptional, (3)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Windsor
Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1715)
The price is AED 620
AED 717 total
includes taxes & fees
29 Sep - 30 Sep
The price is AED 547
AED 600 total
includes taxes & fees
22 Oct - 23 Oct
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Windsor hotels
Recent reviews of Windsor hotels
5/5 Excellent
"This hotel is immaculate. We were pleasantly surprised to have room cleaning each day of our stay. The staff is super friendly and efficient. One small disadvantage, the noise from the street traffic was loud in our room. We would definitely stay there again."
A verified traveler stayed at Hotel Downstreet
Posted 2 days ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
Top Cottages in Other Destinations
More Accommodation Types in Windsor
- Vacation Homes in Windsor (220)
- Apartments in Windsor (76)
- Condo Rentals in Windsor (39)
- B&B in Windsor (27)
- Resorts in Windsor (26)
- Cabin Rentals in Windsor (23)
- Motels in Windsor (20)
- Farmstay in Windsor (16)
- Guest Houses in Windsor (6)
- Aparthotels in Windsor (5)
- Chalets in Windsor (4)
- Inns in Windsor (4)
- Villas in Windsor (4)
- Condo Resorts in Windsor (2)
- Lodges in Windsor (2)
- Hotels (877)