Windsor, MA

Travel Guide

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is AED 397 per night from Apr 7 to Apr 8
AED 397
AED 443 total
includes taxes & fees
7 Apr - 8 Apr
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! (541 reviews)
"Quiet, quick, and easy stay. Clean simple rooms"

Reviewed on 5 April 2025

Life House Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
The price is AED 437 per night from Apr 7 to Apr 8
AED 437
AED 540 total
includes taxes & fees
7 Apr - 8 Apr
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
8.8/10 Excellent! (615 reviews)
"Clean and great location"

Reviewed on 28 March 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is AED 325 per night from Apr 13 to Apr 14
AED 325
AED 363 total
includes taxes & fees
13 Apr - 14 Apr
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (988 reviews)
"Comfortable beds"

Reviewed on 3 April 2025

The Yankee, Trademark Collection by Wyndham
See all 935 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! (1,792 reviews)
"The location to jimney peak was great."

Reviewed on 26 March 2025

Vacation Village in the Berkshires
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
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
Lanesborough
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Jiminy Peak Mountain Resort and Crane ...
9.6/10 Exceptional! (241 reviews)
Quaint Carriage House
"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold."

Reviewed on 12 March 2025

Berkshire Village Carriage House - Super Private!!
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.