Hotels in Chester
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Top Rated Chester Hotels

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
17.2 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

Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
20.56 mi from city center
$93 nightly
The price is $106 total per night
$106 total
Aug 24 - Aug 25
Total includes taxes and fees
Guests of Quality Inn West Springfield enjoy a gym, free WiFi in public areas, and conference space. If you drive, take advantage of free parking. Multilingual staff at the front desk are standing by 24/7 to help with tours or tickets, securing valuables, and dry cleaning/laundry. Other amenities at this golf hotel include a 24-hour business center, a seasonal outdoor pool, and a computer station.
Pool
Breakfast included

La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
Free Cancellation
Reserve now, pay when you stay
22.87 mi from city center
$114 nightly
The price is $129 total per night
$129 total
Aug 21 - Aug 22
Total includes taxes and fees
At La Quinta Inn & Suites by Wyndham Springfield MA, guests enjoy features like 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 tours/tickets and securing valuables. Other amenities at this family-friendly hotel include meeting rooms, conference space, and a 24-hour business center.
Pool
Breakfast included

D. Hotel Suites & Spa
1 Country Club Rd, Holyoke, MA
Free Cancellation
19.08 mi from city center
$158 nightly
The price is $177 total per night
$177 total
Aug 11 - Aug 12
Total includes taxes and fees
D. Hotel Suites & Spa features a full-service spa, an indoor pool, and a gym. The front desk has multilingual staff standing by 24 hours a day to assist with dry cleaning/laundry and securing valuables. Other amenities at this spa hotel include a sauna, a hot tub, and a 24-hour business center.
Pool
Hot Tub

FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
17.39 mi from city center
$79 nightly
The price is $88 total per night
$88 total
Aug 10 - Aug 11
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

Tru by Hilton Chicopee Springfield
440 Memorial Dr, Chicopee, MA
Free Cancellation
Reserve now, pay when you stay
21.84 mi from city center
$110 nightly
The price is $124 total per night
$124 total
Aug 24 - Aug 25
Total includes taxes and fees
At Tru by Hilton Chicopee Springfield, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. You can take advantage of free parking if you drive. Front-desk staff can answer questions 24/7, and assist with luggage storage, securing valuables, and dry cleaning/laundry. Additional amenities include a 24-hour business center, an arcade/game room, and free newspapers.
Pool
Breakfast included

Riverdale Inn
1500 Riverdale Street, On Route 5, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
20.17 mi from city center
$93 nightly
The price is $107 total per night
$107 total
Aug 10 - Aug 11
Total includes taxes and fees
Riverdale Inn offers free WiFi in public areas and coffee in a common area. Free parking is available if you drive. Front-desk staff are standing by 24/7 to assist with any requests.
Parking included
Free WiFi

Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
16.75 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 Northampton
36 King Street, Northampton, MA
Free Cancellation
Reserve now, pay when you stay
18 mi from city center
$166 nightly
The price is $185 total per night
$185 total
Aug 10 - Aug 11
Total includes taxes and fees
Guests of Hotel Northampton enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. There's free parking if you drive. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, luggage storage, and concierge services. Other amenities at this historic hotel include conference space, a 24-hour business center, and coffee/tea in a common area.
Parking included
Free WiFi

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
15.06 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 Ellery
259 Elm Street, Northampton, MA
Free Cancellation
Reserve now, pay when you stay
17.27 mi from city center
$131 nightly
The price is $146 total per night
$146 total
Aug 17 - Aug 18
Total includes taxes and fees
The Ellery features free WiFi in public areas, coffee in a common area, and express check-in. Free parking is included with your stay. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Additional amenities include express check-out, a picnic area, and a fireplace in the lobby.
Breakfast included
Pet friendly

The Red Lion Inn
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
17.02 mi from city center
$230 nightly
The price is $257 total per night
$257 total
Aug 13 - Aug 14
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
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.
Where should you stay in Chester?
What are some of the best hotels in Chester?
Consider these top hotels around Chester:
- Quality Inn West Springfield is located 20.6 mi away, and this hotel has free breakfast, free WiFi, and free parking.
- Berkshire Mountain Lodge is located 17.2 mi away, and this lodge has free WiFi, free parking, and in-room kitchens.
- La Quinta Inn & Suites by Wyndham Springfield MA is located 22.9 mi away, and this hotel has free breakfast, free WiFi, and free parking.
Close to central Chester, you'll find interesting places to visit like Chester Town Hall.
Chester hotels essential information
Accommodation | 833 hotels |
---|---|
Lowest Price | $88 |
Highest Price | $257 |
Popular hotels | Berkshire Mountain Lodge, Quality Inn West Springfield, La Quinta Inn & Suites by Wyndham Springfield MA, D. Hotel Suites & Spa, FairBridge Inn Express, Tru by Hilton Chicopee Springfield, Riverdale Inn, Berkshires Untold, Hotel Northampton, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Ellery, The Red Lion Inn |
Recent Reviews

Berkshire Mountain Lodge
5/5 Excellent
"Amazing place to stay. Can’t wait to go again. "
A verified traveler stayed at Berkshire Mountain Lodge
Posted 18 hours ago
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