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Cheap Holiday Park Resorts in Windsor

Huttopia Berkshires

Huttopia Berkshires

2.5 out of 5
312 Kittle Rd Williamstown MA
Stay at this holiday park in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and ...
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Huttopia Berkshires
See all 993 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.

Top Trending Hotels in Windsor

The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
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 ...
9.2/10 Wonderful! (1,006 reviews)
"Lovely, super clean unit with nice furnishings, however, the dining chair cushions need a good cleaning as the dirt could be seen. There also was candy/gum stuck to one of the cushions and another cushion was completely loose from the chair. There was mention of a "two-burner hotplate" in the description, ..."

Reviewed on Oct 18, 2026

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Opens in a new windowThe Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,215 reviews)
"I had a one BR suite for 4 nights and it was a perfect amount of space for 3 people. Kitchen was very well-equipped and convenient to have for making simple meals and reheating leftovers. While all the cooking utensils/ basics were provided, remember to bring all your oil/ spices as I did. I can't ..."

Reviewed on Oct 19, 2026

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Opens in a new windowBerkshire Mountain Lodge
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,765 reviews)
"Nice place to visit, the rooms were nice and kitchen setup was good. The tub was great, but the shower pressure needs lots of work and the fireplace was miss leading, it was just decoration."

Reviewed on Oct 19, 2026

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Opens in a new windowVacation Village in the Berkshires
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.