Hotels in Chester
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Top Rated Chester Hotels

D. Hotel Suites & Spa
1 Country Club Rd, Holyoke, MA
Free Cancellation
19.08 mi from city center
$134 nightly
The price is $150 total per night
$150 total
Aug 3 - Aug 4
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 securing valuables and dry cleaning/laundry. Other amenities at this spa hotel include a sauna, a hot tub, and a 24-hour business center.
Pool
Hot Tub

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
$118 nightly
The price is $134 total per night
$134 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

Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
20.56 mi from city center
$84 nightly
The price is $96 total per night
$96 total
Aug 10 - Aug 11
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 securing valuables, dry cleaning/laundry, and tours or tickets. Other amenities at this golf hotel include a 24-hour business center, a seasonal outdoor pool, and a computer station.
Pool
Breakfast included

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 3 - Aug 4
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

Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
20.48 mi from city center
$98 nightly
The price is $112 total per night
$112 total
Aug 3 - Aug 4
Total includes taxes and fees
Guests of Red Roof Inn PLUS+ West Springfield enjoy free WiFi in public areas, coffee in a common area, and a TV in a common area. Free parking is included with your stay. The 24-hour front desk has staff always at the ready. Additional amenities include a vending machine and an ATM.
Pet friendly
Parking included

Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
16.75 mi from city center
$199 nightly
The price is $222 total per night
$222 total
Jul 30 - Jul 31
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 water dispenser, and a fireplace in the lobby.
Pet friendly
Parking included

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free Cancellation
15.06 mi from city center
$172 nightly
The price is $192 total per night
$192 total
Jul 30 - Jul 31
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Free Cancellation
18.3 mi from city center
$123 nightly
The price is $137 total per night
$137 total
Aug 4 - Aug 5
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

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
Jul 29 - Jul 30
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

Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
20.08 mi from city center
$127 nightly
The price is $141 total per night
$141 total
Jul 30 - Jul 31
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

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
17.2 mi from city center
$104 nightly
The price is $116 total per night
$116 total
Aug 12 - Aug 13
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

Courtyard by Marriott West Springfield
885 Riverdale Street, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
20.87 mi from city center
$131 nightly
The price is $150 total per night
$150 total
Aug 10 - Aug 11
Total includes taxes and fees
Guests staying at Courtyard by Marriott West Springfield enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is included with your stay. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and securing valuables. Additional amenities include conference space, a 24-hour business center, and express check-in.
Pool
Parking included
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:
- D. Hotel Suites & Spa is located 19.1 mi away, and this hotel has a full-service spa, 2 restaurants, and a fitness center.
- 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.
- Quality Inn West Springfield is located 20.5 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 | 836 hotels |
---|---|
Lowest Price | $88 |
Highest Price | $222 |
Popular hotels | D. Hotel Suites & Spa, La Quinta Inn & Suites by Wyndham Springfield MA, Quality Inn West Springfield, Tru by Hilton Chicopee Springfield, Red Roof Inn PLUS+ West Springfield, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Holiday Inn & Suites Pittsfield-Berkshires by IHG, FairBridge Inn Express, Best Western Plus Berkshire Hills Inn & Suites, Berkshire Mountain Lodge, Courtyard by Marriott West Springfield |
Recent Reviews

D. Hotel Suites & Spa
5/5 Excellent
Wonderful Stay!
"My husband and I celebrated our 15 year anniversary at the D Hotel and Spa. The staff went above and beyond decorating our room making it incredibly special for us. We stayed in the one bedroom double queen suite with our two kids. The staff also included treats for our kids. This stay is something our family looks forward to every year and we already cant wait to come back. The room was clean and comfy. The pool and jacuzzi was awesome. Our spa experience was awesome. Breakfast was delicious! We had a wonderful time!"
A verified traveler stayed at D. Hotel Suites & Spa
Posted 2 days ago
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