Hotels in Cheshire

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Jun 30 - Jul 1
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Check prices in Cheshire for tonight, Jun 30 - Jul 1
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Top Rated Cheshire Hotels

The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
12.18 mi from city center
$159 nightly
The price is $178 total per night
$178 total
Jul 6 - Jul 7
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 tours or tickets, 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
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
6.49 mi from city center
$143 nightly
The price is $159 total per night
$159 total
Jul 6 - Jul 7
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
$162 nightly
The price is $181 total per night
$181 total
Jul 29 - Jul 30
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
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
20.76 mi from city center
$187 nightly
The price is $209 total per night
$209 total
Jul 6 - Jul 7
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 securing valuables, luggage storage, and dry cleaning/laundry. 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
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
$167 nightly
The price is $187 total per night
$187 total
Jul 1 - Jul 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 water dispenser, and a fireplace in the lobby.
Pet friendly
Parking included
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free Cancellation
11.83 mi from city center
$171 nightly
The price is $191 total per night
$191 total
Jul 6 - Jul 7
Total with taxes and fees
At Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The front desk is staffed 24 hours a day to help with concierge services and securing valuables. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

2.5 out of 5
170 Housatonic Street Lee MA
Free Cancellation
Reserve now, pay when you stay
18.52 mi from city center
$135 nightly
The price is $151 total per night
$151 total
Jul 27 - Jul 28
Total with taxes and fees
At Quality Inn Lee - Lenox South, guests have access to free WiFi in public areas, express check-in, and express check-out. Onsite parking is offered for a fee. The front desk is staffed 24/7 to help with tours or tickets, and answer any questions about the accommodations. This hotel also has free newspapers.
Breakfast included
Free WiFi
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
8.83 mi from city center
$249 nightly
The price is $278 total per night
$278 total
Jul 7 - Jul 8
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 concierge services, 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
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
6.73 mi from city center
$63 nightly
The price is $70 total per night
$70 total
Jul 2 - Jul 3
Total with taxes and fees
Guests of FairBridge Inn Express enjoy access to free WiFi in public areas, meeting rooms, and a business center. If you drive, put free parking to good use. Front-desk staff are standing by 24/7 to assist with any requests. This motel also has laundry facilities.
Parking included
Free WiFi
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
$135 nightly
The price is $151 total per night
$151 total
Jul 5 - Jul 6
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, dry cleaning/laundry, and securing valuables. 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
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
20.67 mi from city center
$181 nightly
The price is $203 total per night
$203 total
Jul 22 - Jul 23
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
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
9.78 mi from city center
$154 nightly
The price is $172 total per night
$172 total
Jul 2 - Jul 3
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
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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
989 hotels
Lowest Price
$70
Highest Price
$278
Popular hotels
The Yankee Inn, Vacation Village in the Berkshires, Berkshire Mountain Lodge, The Red Lion Inn, Berkshires Untold, Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG, Quality Inn Lee - Lenox South, Hotel On North, FairBridge Inn Express, Best Western Plus Berkshire Hills Inn & Suites, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Hotel Downstreet, an Ascend Collection Hotel

Recent Reviews

The Yankee Inn

The Yankee Inn

5/5 Excellent
"Warm and welcoming. Comfortable room. Generous breakfast buffet. Having a charging station for our hybrid was a pleasant surprise Proximity to Tanglewood was also a plus."
A verified traveler stayed at The Yankee Inn
Posted less than an hour ago
The Yankee Inn

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