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 prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 65 Cottages in Windsor with updated reviews, rates, and availability.

The Clearing - Quiet - Close To Nature
The Clearing - Quiet - Close To Nature
10.0 out of 10, Exceptional, (187)

Family-Friendly Richmond Cottage w/ Private Yard
Family-Friendly Richmond Cottage w/ Private Yard
10.0 out of 10, Exceptional, (4)

Charming historic cottage on scenic road to Mt. Greylock
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (107)

Beachwood Cottage
Beachwood Cottage
10.0 out of 10, Exceptional, (3)

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
10.0 out of 10, Exceptional, (1)

Private Lake Cottage on 3 acres w/350 sq. ft. deck
Private Lake Cottage on 3 acres w/350 sq. ft. deck

Lake Views & Dock Access - Pittsfield Cottage!
Lake Views & Dock Access - Pittsfield Cottage!
10.0 out of 10, Exceptional, (1)

Picturesque Cottage with Sunroom on Ashmere Lake!
Picturesque Cottage with Sunroom on Ashmere Lake!
9.4 out of 10, Exceptional, (21)
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, (1792)
The price is AED 476
AED 563 total
includes taxes & fees
3 Apr - 4 Apr

Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (925)
The price is AED 547
AED 600 total
includes taxes & fees
2 Apr - 3 Apr

The Ponds at Foxhollow
The Ponds at Foxhollow
8.6 out of 10, Excellent, (120)
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

Life House Berkshires
5/5 Excellent
"Cool vibe. Nice rooms and bedding. Would return!"
A verified traveler stayed at Life House Berkshires
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
- Apartments in Windsor
- Condo Rentals in Windsor
- Resorts in Windsor
- B&B in Windsor
- Farmstay in Windsor
- Cabin Rentals in Windsor
- Motels in Windsor
- Guest Houses in Windsor
- Chalets in Windsor
- Aparthotels in Windsor
- Inns in Windsor
- Villas in Windsor
- Condo Resorts in Windsor
- Lodges in Windsor
- Hotels