Book 2 Star Hotels in Chester
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Featured Chester 2 Stars Hotels

The Black Swan Lee - Lenox, an Ascend Collection Hotel
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.
Breakfast included
Pet friendly

The Ellery
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
Mar 31 - Apr 1
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.
Breakfast included
Pet friendly

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
$130 nightly
The price is $145 total per night
$145 total
Apr 1 - Apr 2
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

Berkshires Untold
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 30 - Mar 31
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.
Pet friendly
Parking included

The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
17.05 mi from city center
$98 nightly
The price is $110 total per night
$110 total
Mar 30 - Mar 31
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.
Pool
Hot Tub

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
Apr 27 - Apr 28
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

D. Hotel Suites & Spa
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.
Pool
Hot Tub

Blue – A Modern Hotel, an Ascend Collection Hotel
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.
Parking included
Free WiFi

Baldwin Inn & Suites, SureStay Collection by Best Western
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.
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.
Chester hotels essential information
Accommodation | 873 hotels |
|---|---|
Lowest Price | $87 |
Highest Price | $155 |
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 |
Recent Reviews

D. Hotel Suites & Spa
5/5 Excellent
"No complaints."
A verified traveler stayed at D. Hotel Suites & Spa
Posted less than an hour ago


