Hotels in Chester

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Mar 28 - Mar 29
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Check prices in Chester for tonight, Mar 28 - Mar 29
Mar 29 - Mar 30
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Top Rated Chester Hotels

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Free Cancellation
19.08 mi from city center
$134 nightly
The price is $149 total per night
$149 total
Mar 30 - Mar 31
Total with 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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
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
Apr 26 - Apr 27
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.
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
16.75 mi from city center
$78 nightly
The price is $87 total per night
$87 total
Mar 29 - Mar 30
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 fireplace in the lobby, and a water dispenser.
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
15.06 mi from city center
$130 nightly
The price is $145 total per night
$145 total
Mar 30 - Mar 31
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.
Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western

2.5 out of 5
21 Baldwin Street West Springfield MA
Free Cancellation
Reserve now, pay when you stay
22.47 mi from city center
$101 nightly
The price is $116 total per night
$116 total
Apr 5 - Apr 6
Total with taxes and fees
Guests staying at Baldwin Inn & Suites, SureStay Collection by Best Western enjoy free WiFi in public areas, express check-out, and a TV in a common area. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include a vending machine and a water dispenser.
Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 out of 5
1080 Riverdale St West Springfield MA
Free Cancellation
20.62 mi from city center
$111 nightly
The price is $128 total per night
$128 total
Apr 26 - Apr 27
Total with taxes and fees
Renovated in 2025, Blue – A Modern Hotel, an Ascend Collection Hotel offers a 24-hour gym, free WiFi in public areas, and coffee in a common area. If you decide to drive, there's free parking. Multilingual staff at the front desk are standing by 24/7 to help with access to locker space, securing valuables, and dry cleaning/laundry. Additional amenities include a computer station, express check-out, and free newspapers.
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
14.66 mi from city center
$94 nightly
The price is $105 total per night
$105 total
Apr 6 - Apr 7
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.
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
17.05 mi from city center
$98 nightly
The price is $110 total per night
$110 total
Mar 29 - Mar 30
Total with 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, a seasonal outdoor pool, and coffee/tea in a common area.
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
Free Cancellation
Reserve now, pay when you stay
17.28 mi from city center
$139 nightly
The price is $155 total per night
$155 total
Apr 7 - Apr 8
Total with 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 fireplace in the lobby, and a garden.
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr Chicopee MA
Free Cancellation
Reserve now, pay when you stay
21.78 mi from city center
$106 nightly
The price is $120 total per night
$120 total
Apr 7 - Apr 8
Total with 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 dry cleaning/laundry, luggage storage, and securing valuables. Additional amenities include a 24-hour business center, an arcade/game room, and free newspapers.
Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst

3 out of 5
115A Conz Street Northampton MA
Free Cancellation
Reserve now, pay when you stay
18.16 mi from city center
$152 nightly
The price is $170 total per night
$170 total
Apr 1 - Apr 2
Total with taxes and fees
Guests staying at Fairfield Inn & Suites Springfield Northampton/Amherst enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. You can take advantage of free parking if you drive. The 24-hour front desk has staff standing by to help with luggage storage, securing valuables, and dry cleaning/laundry. Additional amenities include meeting rooms, a business center, and coffee/tea in a common area.
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
17.02 mi from city center
$189 nightly
The price is $211 total per night
$211 total
Apr 7 - Apr 8
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. The 24-hour front desk has multilingual staff ready to assist with concierge services, dry cleaning/laundry, and luggage storage. Other amenities at this historic hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
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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.

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.
  • Berkshire Mountain Lodge is located 17.2 mi away, and this lodge has free WiFi, free parking, and in-room kitchens.
  • Berkshires Untold is located 16.8 mi away, and this lodge has free WiFi, free parking, and concierge services.

Chester hotels essential information

Accommodation
873 hotels
Lowest Price
$87
Highest Price
$211
Popular hotels
D. Hotel Suites & Spa, Berkshire Mountain Lodge, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Baldwin Inn & Suites, SureStay Collection by Best Western, Blue – A Modern Hotel, an Ascend Collection Hotel, The Black Swan Lee - Lenox, an Ascend Collection Hotel, The Yankee, Trademark Collection by Wyndham, The Ellery, Tru by Hilton Chicopee Springfield, Fairfield Inn & Suites Springfield Northampton/Amherst, The Red Lion Inn

Recent Reviews

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western

2/5 Poor
"The bed was covered in someone’s hair. Like loads of it. In the sheets. On the pillows. On the comforter. It was disgusting. Parking was fine. Air conditioner kind of worked. Front desk staff was great. The rest, not so much. "
A verified traveler stayed at Baldwin Inn & Suites, SureStay Collection by Best Western
Posted 11 hours ago
Baldwin Inn & Suites, SureStay Collection by Best Western

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