Windsor, MA

Travel Guide

Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
The price is AED 400 per night from Mar 10 to Mar 11
AED 400
AED 476 total
includes taxes & fees
10 Mar - 11 Mar
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,771 reviews)
"Awesome place extremely close to the ski mnt. Has an inside / outside pool plus hot tub! Rooms were great"

Reviewed on 2 March 2025

Vacation Village in the Berkshires
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
The price is AED 434 per night from Mar 20 to Mar 21
AED 434
AED 485 total
includes taxes & fees
20 Mar - 21 Mar
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,002 reviews)
"Exactly what I needed after being stressed out from work for the past few months. The laundry service may have out of service, but I dont care. All I needed was to decompress and this hotel helped me do exactly that. Thank you for a lovely weekend and I'll definitely come back when I get the ..."

Reviewed on 3 March 2025

Hotel Downstreet
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is AED 355 per night from Mar 19 to Mar 20
AED 355
AED 397 total
includes taxes & fees
19 Mar - 20 Mar
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (513 reviews)
"This is not your standard chain hotel. Although the overall architecture is 1970s motel style, the color choices, furnishings, and materials used in upgrading have produced a very sophisticated, upscale ambience. Life House Berkshire is promoted as a writer’s retreat. The lobby/bar appears to be ..."

Reviewed on 3 March 2025

Life House Berkshires
See all 929 properties in Windsor
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.
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,771 reviews)
"Awesome place extremely close to the ski mnt. Has an inside / outside pool plus hot tub! Rooms were great"

Reviewed on 2 March 2025

Vacation Village in the Berkshires
The Ponds at Foxhollow by Capital Vacations
The Ponds at Foxhollow by Capital Vacations
3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
Stay at this 3-star condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions The Mount and Wyndhurst Golf & Club are located ...
8.6/10 Excellent! (120 reviews)
"Very comfortable property in a lovely setting"

Reviewed on 18 December 2024

The Ponds at Foxhollow by Capital Vacations
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3 out of 5
37 Corey Rd, Hancock, MA
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 bars/lounges. Our guests praise the property condition in our reviews. Popular ...
8.2/10 Very Good! (925 reviews)
"Staff was exceptionally helpful and friendly."

Reviewed on 14 January 2025

Jiminy Peak Mountain Resort
See all properties in Windsor
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.