Hotels in Cheshire
Search over 996 hotels from $88
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Top Rated Cheshire Hotels
Harbour House Inn
725 North State Road, Cheshire, MA
1.22 mi from city center
$262 nightly
The price is $277 total per night
$277 total
Aug 14 - Aug 15
Total includes taxes and fees
At Harbour House Inn, guests have access to free WiFi in public areas, coffee in a common area, and a library. A stay here includes free parking. Additional amenities include express check-in, express check-out, and a communal living room.
Breakfast included
Parking included
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
6.49 mi from city center
$130 nightly
The price is $145 total per night
$145 total
Aug 27 - Aug 28
Total includes 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
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
11.54 mi from city center
$108 nightly
The price is $120 total per night
$120 total
Sep 7 - Sep 8
Total includes 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
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
6.73 mi from city center
$79 nightly
The price is $88 total per night
$88 total
Aug 12 - Aug 13
Total includes 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
The Williams Inn
101 Spring Street, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
10.41 mi from city center
$233 nightly
The price is $260 total per night
$260 total
Sep 7 - Sep 8
Total includes 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, securing valuables, and dry cleaning/laundry. Additional amenities include coffee/tea in a common area, a terrace, and a banquet hall.
Pet friendly
Parking included
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
13.38 mi from city center
$178 nightly
The price is $199 total per night
$199 total
Sep 1 - Sep 2
Total includes 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
Hotel Downstreet, Ascend Hotel Collection
40 Main St, North Adams, MA
Free Cancellation
Reserve now, pay when you stay
9.81 mi from city center
$144 nightly
The price is $160 total per night
$160 total
Sep 9 - Sep 10
Total includes taxes and fees
Guests of Hotel Downstreet, Ascend Hotel Collection 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 a banquet hall.
Pool
Hot Tub
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
$110 nightly
The price is $123 total per night
$123 total
Sep 8 - Sep 9
Total includes 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
The Red Lion Inn
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
20.76 mi from city center
$229 nightly
The price is $256 total per night
$256 total
Aug 12 - Aug 13
Total includes 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 concierge services, dry cleaning/laundry, and securing valuables. Other amenities at this historic hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
12.18 mi from city center
$134 nightly
The price is $150 total per night
$150 total
Sep 8 - Sep 9
Total includes 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 concierge services, and answer any questions about the area. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Free Cancellation
9.16 mi from city center
$115 nightly
The price is $128 total per night
$128 total
Sep 1 - Sep 2
Total includes 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 dry cleaning/laundry, tours or tickets, and luggage storage. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
11.64 mi from city center
$119 nightly
The price is $133 total per night
$133 total
Sep 1 - Sep 2
Total includes 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
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.
How much is a Cheshire hotel?
Check Cheshire hotel room prices by star rating
4 Star Hotels
11 properties
What's the best place for a stay in Cheshire?
What are the best hotels in Cheshire?
Consider these top hotels around Cheshire:
- Harbour House Inn is a B&B offering free breakfast, free WiFi, and free parking.
- Vacation Village in the Berkshires is located 6.5 mi away, and this condo has free parking, private patios, and a fitness center.
- Berkshire Mountain Lodge is located 11.5 mi away, and this lodge has free WiFi, free parking, and in-room kitchens.
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 | 996 hotels |
|---|---|
Lowest Price | $88 |
Highest Price | $277 |
Popular hotels | Harbour House Inn, Vacation Village in the Berkshires, Berkshire Mountain Lodge, FairBridge Inn Express, The Williams Inn, Berkshires Untold, Hotel Downstreet, Ascend Hotel Collection, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Red Lion Inn, The Yankee, Trademark Collection by Wyndham, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Best Western Plus Berkshire Hills Inn & Suites |
Recent Reviews
Vacation Village in the Berkshires
5/5 Excellent
"This Vacation Village is amazing, returning this week for a little time away. Stayed last week for work and came home and planned a 3 day trip based on the location. "
A verified traveler stayed at Vacation Village in the Berkshires
Posted 2 days ago
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