Hotels in Cheshire

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May 15 - May 16
Tonight
Check prices in Cheshire for tonight, May 15 - May 16
May 16 - May 17
Tomorrow night
Check prices in Cheshire for tomorrow night, May 16 - May 17

Top Rated Cheshire Hotels

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
11.54 mi from city center
$113 nightly
The price is $126 total per night
$126 total
May 24 - May 25
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
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
$119 nightly
The price is $133 total per night
$133 total
May 21 - May 22
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 water dispenser, and a fireplace in the lobby.
Pet friendly
Parking included
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
$110 nightly
The price is $123 total per night
$123 total
May 17 - May 18
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
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Free Cancellation
9.78 mi from city center
$143 nightly
The price is $160 total per night
$160 total
May 19 - May 20
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 Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
20.76 mi from city center
$200 nightly
The price is $223 total per night
$223 total
May 27 - May 28
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. If you drive, take advantage of free parking. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, securing valuables, and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this golf hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
12.32 mi from city center
$119 nightly
The price is $133 total per night
$133 total
May 25 - May 26
Total with taxes and fees
Guests staying at Hampton Inn & Suites Berkshires-Lenox enjoy an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls, an off-leash area, and litter boxes. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Breakfast included
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
20.67 mi from city center
$134 nightly
The price is $149 total per night
$149 total
May 18 - May 19
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 a terrace.
Pool
Air conditioning
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
Free Cancellation
17.32 mi from city center
$121 nightly
The price is $135 total per night
$135 total
May 27 - May 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
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Free Cancellation
Reserve now, pay when you stay
10.41 mi from city center
$266 nightly
The price is $298 total per night
$298 total
May 17 - May 18
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 luggage storage, securing valuables, and concierge services. Additional amenities include coffee/tea in a common area, a terrace, and wedding services.
Pet friendly
Parking included
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
8.83 mi from city center
$169 nightly
The price is $189 total per night
$189 total
May 17 - May 18
Total with taxes and fees
Hotel On North features free WiFi in public areas, meeting rooms, and a business center. There's free parking if you drive. Front-desk staff can answer questions 24/7, and 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 food and water bowls. Additional amenities include coffee/tea in a common area, an ATM, and a banquet hall.
Pet friendly
Parking included
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
12.18 mi from city center
$109 nightly
The price is $122 total per night
$122 total
May 17 - May 18
Total with taxes and fees
The Yankee Inn features an indoor pool, an outdoor pool, and a 24-hour gym. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Additional amenities include free WiFi in public areas, a hot tub, and a seasonal outdoor pool.
Pool
Hot Tub
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
13.94 mi from city center
$155 nightly
The price is $173 total per night
$173 total
May 28 - May 29
Total with taxes and fees
Guests staying at Courtyard by Marriott Lenox Berkshires enjoy an indoor pool, a gym, and free WiFi in public areas. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, securing valuables, and luggage storage. Additional amenities include a 24-hour business center, a meeting room, and express check-in.
Pool
Parking included
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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
1,015 hotels
Lowest Price
$122
Highest Price
$298
Popular hotels
Berkshire Mountain Lodge, Berkshires Untold, Vacation Village in the Berkshires, Hotel Downstreet, an Ascend Collection Hotel, The Red Lion Inn, Hampton Inn & Suites Berkshires-Lenox, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel, The Williams Inn, Hotel On North, The Yankee Inn, Courtyard by Marriott Lenox Berkshires

Recent Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

5/5 Excellent
"Clean and great job staffing "
A verified traveler stayed at Berkshire Mountain Lodge
Posted 6 hours ago
Berkshire Mountain Lodge

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