Windsor Holidays

Name: Berkshires Untold
Price range: AU$111
Rating: 9

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Your Windsor Holiday

Our holiday packages to Windsor let you customise your own adventure. Tailor your journey to your interests and style and make the most of your time in this interesting city. Want some sightseeing tips for your trip to Windsor? Wahconah Falls State Park and Bas Ridge Golf Course are two of the main attractions here. Whatever your travel plans or the size of your budget, organising a tailored Windsor holiday is a walk in the park with Expedia.

Windsor Holiday

Windsor Essential Information

Language	English
Currency	U.S dollars
Population	890
Max Temp Winter	-1.11ºC
Max Temp Summer	24ºC
Top Sights	Berkshire Museum, Colonial Theatre and Barrington Stage Company

Our pick of the best Windsor Hotel Deals

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Fully refundable

AU$186

8 Apr - 9 Apr

includes taxes & fees

8.8/10 Excellent! (1,000 reviews)

For the price, is a good property. Convenient for our purposes. While not up to more modern standards, it is reasonably furnished. Location is a bit noisy due to traffic and trains. Limited decent food options.

Reviewed on 5 Mar 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Fully refundableReserve now, pay when you stay

AU$174

22 Mar - 23 Mar

includes taxes & fees

9/10 Wonderful! (879 reviews)

The room is cozy and the kitchen is great. The pool area needs renovation but my kids still love the fact the pool is huge. Only downside is it takes forever to get your $150 deposit refunded:( every time and I leave the room spotless.

Reviewed on 17 Mar 2026

Berkshires Untold

194 Pittsfield Rd Lenox MA

Fully refundableReserve now, pay when you stay

AU$111

1 Apr - 2 Apr

includes taxes & fees

9/10 Wonderful! (876 reviews)

I always sleep the best here. So quiet and comfortable. Love the lounge area. Bartender really nice. Had a lovely cheese plate. Shower is great. Great value!

Reviewed on 18 Mar 2026

See all 1,000 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.