Hotels in Cheshire

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Sep 30 - Oct 1
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Top Rated Cheshire Hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
6.49 mi from city center
$128 nightly
The price is $143 total per night
$143 total
Oct 1 - Oct 2
Total with taxes and fees
Vacation Village in the Berkshires features an indoor pool, an outdoor pool, and a children's pool. If you decide to drive, there's free parking. The front desk is staffed 24 hours a day to help with access to locker space and concierge services. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.
Pool
Parking included
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
11.54 mi from city center
$128 nightly
The price is $143 total per night
$143 total
Oct 2 - Oct 3
Total with taxes and fees
At Berkshire Mountain Lodge, guests have access to an indoor pool, free WiFi in public areas, and a hot tub. If you decide to drive, there's free parking. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this golf lodge include a business center, an arcade/game room, and laundry facilities.
Pool
Hot Tub
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
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
$142 nightly
The price is $159 total per night
$159 total
Oct 2 - Oct 3
Total with taxes and fees
Guests staying at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG enjoy features like 2 indoor pools, 2 outdoor pools, and a business center. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this family-friendly hotel include a seasonal outdoor pool, an arcade/game room, and express check-out.
Pool
Air conditioning
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
13.38 mi from city center
$128 nightly
The price is $143 total per night
$143 total
Oct 1 - Oct 2
Total with taxes and fees
Renovated in 2023, Berkshires Untold offers free WiFi in public areas, coffee in a common area, and express check-in. You can take advantage of free parking if you drive. The front desk is staffed 24/7 to help with concierge services, and answer any questions about the accommodations. Additional amenities include a terrace, a fireplace in the lobby, and a water dispenser.
Pet friendly
Parking included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
20.76 mi from city center
$219 nightly
The price is $245 total per night
$245 total
Oct 30 - Oct 31
Total with taxes and fees
Guests of The Red Lion Inn have access to an outdoor pool, a gym, and free WiFi in public areas. The 24-hour front desk has multilingual staff ready to assist with securing valuables, dry cleaning/laundry, and luggage storage. Other amenities at this historic hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
10.41 mi from city center
$237 nightly
The price is $265 total per night
$265 total
Oct 29 - Oct 30
Total with taxes and fees
At The Williams Inn, guests have access to a gym, free WiFi in public areas, and a conference center. If you drive, put free parking to good use. The front desk is staffed 24/7 to help with concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include coffee/tea in a common area, a terrace, and a gift shop.
Pet friendly
Parking included
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
9.8 mi from city center
$145 nightly
The price is $162 total per night
$162 total
Oct 29 - Oct 30
Total with taxes and fees
Guests of Hotel Downstreet, an Ascend Collection Hotel have access to an indoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking if you drive. The front desk is staffed 24 hours a day to help with luggage storage and securing valuables. Additional amenities include a hot tub, express check-out, and laundry facilities.
Pool
Hot Tub
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St, Lee, MA
17.32 mi from city center
$115 nightly
The price is $128 total per night
$128 total
Oct 27 - Oct 28
Total with taxes and fees
Guests of The Black Swan Lee - Lenox, an Ascend Collection Hotel enjoy a 24-hour gym, free WiFi in public areas, and a 24-hour business center. If you plan to drive, free parking is available. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include coffee/tea in a common area, a microwave in a common area, and a meeting room.
Breakfast included
Pet friendly
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
9.16 mi from city center
$98 nightly
The price is $109 total per night
$109 total
Oct 31 - Nov 1
Total with taxes and fees
Guests of Holiday Inn & Suites Pittsfield-Berkshires by IHG have access to an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, dry cleaning/laundry, and luggage storage. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
12.18 mi from city center
$116 nightly
The price is $130 total per night
$130 total
Oct 1 - Oct 2
Total with taxes and fees
Guests staying at The Yankee, Trademark Collection by Wyndham enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with tours or tickets, and answer any questions about the area. Additional amenities include a hot tub, a seasonal outdoor pool, and coffee/tea in a common area.
Pool
Hot Tub
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
6.62 mi from city center
$149 nightly
The price is $166 total per night
$166 total
Oct 19 - Oct 20
Total with taxes and fees
At Jiminy Peak Mountain Resort, guests enjoy ski-in/ski-out access, an outdoor pool, and a gym. You can put free parking to good use if you drive. Front-desk staff can answer questions 24/7, and assist with tours or tickets, luggage storage, and securing valuables. Other amenities at this ski condominium resort include 2 hot tubs, outdoor tennis courts, and free WiFi in public areas.
Pool
Hot Tub
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
11.64 mi from city center
$114 nightly
The price is $127 total per night
$127 total
Oct 2 - Oct 3
Total with taxes and fees
Guests of Best Western Plus Berkshire Hills Inn & Suites enjoy a gym, free WiFi in public areas, and conference space. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a 24-hour business center, coffee/tea in a common area, and a computer station.
Breakfast included
Pet friendly
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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.

What's the best place for a stay in Cheshire?

What are the best hotels in Cheshire?

Consider these top hotels around Cheshire:

What are the best hotels to stay near St Mary's of the Assumption Church?

St Mary's of the Assumption Church ought to be around the top of your to-do list while you're visiting Cheshire. This well-known church is 0.4 miles from the downtown area and lures travelers from all over the place. Get the most out of your visit by basing yourself at 19th c. Renovated Barn in the Berkshires, just 1 mile away. Other top-rated hotels include Harbour House Inn, located 1 mile away, and Private Suite With Separate Entrance in a Quiet Berkshire Neighborhood, which is 2 miles away. You'll be able to leap out of bed and be at this attraction soon after!

Cheshire hotels essential information

Accommodation
1,007 hotels
Lowest Price
$109
Highest Price
$265
Popular hotels
Vacation Village in the Berkshires, Berkshire Mountain Lodge, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Berkshires Untold, The Red Lion Inn, The Williams Inn, Hotel Downstreet, an Ascend Collection Hotel, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, Jiminy Peak Mountain Resort, Best Western Plus Berkshire Hills Inn & Suites

Recent Reviews

Berkshires Untold

Berkshires Untold

5/5 Excellent
"It was ideal"
A verified traveler stayed at Berkshires Untold
Posted 3 days ago
Berkshires Untold

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