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
$106 nightly
The price is $118 total per night
$118 total
Dec 14 - Dec 15
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 aparthotel 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 $150 total per night
$150 total
Dec 14 - Dec 15
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 that can help 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

Blue A Modern Hotel, an Ascend Collection Hotel
1080 Riverdale St West Springfield MA
Free Cancellation
20.47 mi from city center
$104 nightly
The price is $119 total per night
$119 total
Dec 9 - Dec 10
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. 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 computer station, express check-out, and a vending machine.
Parking included
Free WiFi

The Yankee Inn
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
17.05 mi from city center
$123 nightly
The price is $138 total per night
$138 total
Nov 23 - Nov 24
Total with taxes and fees
The Yankee Inn features an indoor pool, an outdoor pool, and a 24-hour gym. 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 free WiFi in public areas, a hot tub, and a seasonal outdoor pool.
Pool
Hot Tub

Riverdale Inn
1500 Riverdale Street 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
Nov 15 - Nov 16
Total with 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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
190 Meadow Street South Lee MA
Free Cancellation
14.96 mi from city center
$128 nightly
The price is $143 total per night
$143 total
Nov 15 - Nov 16
Total with taxes and fees
Guests staying at Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires enjoy features like 2 indoor pools, 2 outdoor pools, and a business center. Front-desk staff can assist with dry cleaning/laundry and securing valuables. Other amenities at this ski hotel include a seasonal outdoor pool, an arcade/game room, and a terrace.
Pool
Air conditioning

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
$111 nightly
The price is $125 total per night
$125 total
Nov 16 - Nov 17
Total with 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 securing valuables and tours/tickets. Other amenities at this family-friendly hotel include meeting rooms, conference space, and a 24-hour business center.
Pool
Breakfast included

The Red Lion Inn
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
17.02 mi from city center
$197 nightly
The price is $220 total per night
$220 total
Nov 29 - Nov 30
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. If you drive, take advantage of free parking. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, luggage storage, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this golf hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa

Berkshires Untold
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
16.75 mi from city center
$118 nightly
The price is $132 total per night
$132 total
Nov 17 - Nov 18
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

Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street West Springfield MA
Free Cancellation
Reserve now, pay when you stay
20.44 mi from city center
$86 nightly
The price is $99 total per night
$99 total
Dec 1 - Dec 2
Total with taxes and fees
Guests of Red Roof Inn PLUS+ West Springfield enjoy free WiFi in public areas, coffee in a common area, and an ATM. Free parking is included with your stay. The 24-hour front desk has staff always at the ready. Additional amenities include a TV in a common area and a vending machine.
Pet friendly
Parking included

Hotel On North
297 North Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
18.41 mi from city center
$112 nightly
The price is $125 total per night
$125 total
Nov 29 - Nov 30
Total with taxes and fees
Hotel On North features free WiFi in public areas, meeting rooms, and a business center. There's free parking if you drive. The front desk is staffed 24 hours a day to help with concierge services and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this family-friendly hotel include coffee/tea in a common area, an ATM, and a banquet hall.
Pet friendly
Parking included

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Free Cancellation
17 mi from city center
$103 nightly
The price is $115 total per night
$115 total
Dec 13 - Dec 14
Total with taxes and fees
At Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The front desk is staffed 24 hours a day to help with concierge services and securing valuables. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub
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.
Stay near popular Chester attractions
Where should you stay in Chester?
What are some of the best hotels in Chester?
Consider these top hotels around Chester:
- Berkshire Mountain Lodge is located 17.2 mi away, and this aparthotel has free WiFi, free parking, and in-room kitchens.
- D. Hotel Suites & Spa is located 19.1 mi away, and this hotel has a full-service spa, 2 restaurants, and free breakfast.
- Hampton Inn West Springfield is located 20.8 mi away, and this hotel has free breakfast, free WiFi, and free parking.
Chester hotels essential information
Accommodation | 880 hotels |
|---|---|
Lowest Price | $99 |
Highest Price | $220 |
Popular hotels | Berkshire Mountain Lodge, D. Hotel Suites & Spa, Blue A Modern Hotel, an Ascend Collection Hotel, The Yankee Inn, Riverdale Inn, Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires, La Quinta Inn & Suites by Wyndham Springfield MA, The Red Lion Inn, Berkshires Untold, Red Roof Inn PLUS+ West Springfield, Hotel On North, Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG |
Recent Reviews

D. Hotel Suites & Spa
4/5 Good
"A decent place for travellers"
A verified traveler stayed at D. Hotel Suites & Spa
Posted 2 hours ago
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