Cheshire Holiday Packages

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Top Cheshire hotels

Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$226 per night from 21 Apr to 22 Apr
AU$226
includes taxes & fees
21 Apr - 22 Apr
Berkshires Untold: Pet-friendly lodge with free WiFi and free parking. Guests love the helpful staff!
"The hotel is cozy and charming. The rooms are well-appointed. The staff was great. Easy check-in, check-out. The bar is well stocked and they offer free (real) coffee in the morning!"

Reviewed on 14 Apr. 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
Fully refundableReserve now, pay when you stay
The price is AU$209 per night from 28 Apr to 29 Apr
AU$209
includes taxes & fees
28 Apr - 29 Apr
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Family-friendly hotel with 2 outdoor pools and a poolside bar. Located near ...
"Great deal for villa resort suite. Lots of space, great condition, great amenities, great location."

Reviewed on 12 Apr. 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
Fully refundableReserve now, pay when you stay
The price is AU$170 per night from 28 Apr to 29 Apr
AU$170
includes taxes & fees
28 Apr - 29 Apr
The Yankee, Trademark Collection by Wyndham: Business-friendly hotel with free breakfast and free WiFi. Located near skiing.
"This place was being remodeled and had I known I would have stayed elsewhere."

Reviewed on 16 Apr. 2025

The Yankee, Trademark Collection by Wyndham
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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.