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 SAR 326 per night from Sep 25 to Sep 26
SAR 326
SAR 405 total
25 Sep - 26 Sep
includes taxes & fees
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,921 reviews)
"Very enjoyable stay in a beautiful location! Clean, comfy, and nicely decorated condo! The staff is so helpful, and absolutely amazing. Couldn’t have had a better place to stay!"

Reviewed on 3 September 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
The price is SAR 571 per night from Oct 5 to Oct 6
SAR 571
SAR 722 total
5 Oct - 6 Oct
includes taxes & fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (624 reviews)
"Nice staff, clean, and lots of apace in the rooms."

Reviewed on 9 September 2025

Berkshire Mountain Lodge
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is SAR 571 per night from Sep 15 to Sep 16
SAR 571
SAR 637 total
15 Sep - 16 Sep
includes taxes & fees
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! (999 reviews)
"I would have liked a better breakfast bar."

Reviewed on 6 September 2025

Hotel Downstreet, an Ascend Collection Hotel
See all 984 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 a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,921 reviews)
"Very enjoyable stay in a beautiful location! Clean, comfy, and nicely decorated condo! The staff is so helpful, and absolutely amazing. Couldn’t have had a better place to stay!"

Reviewed on 3 September 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 hot tubs. Our guests praise the property condition in our reviews. Popular ...
8.2/10 Very Good! (974 reviews)
"Staff was very nice and helpful. Property was a little bit outdated but very clean and functional. Surroundings are beautiful!!"

Reviewed on 9 September 2025

Jiminy Peak Mountain Resort
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd, Williamstown, MA
Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
10/10 Exceptional! (4 reviews)
"Great Time! Beautiful new tents with all the items you need to Glamp with from silverware to tupperware. Comfy beds and comforter! Everyone was so nice and you know they love what they do! Next fall/foiliage camping in the trapper with the wood stove !"

Reviewed on 25 August 2025

Huttopia Berkshires
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.