Hotels in Chester

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May 14 - May 15
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Check prices in Chester for tonight, May 14 - May 15
May 15 - May 16
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Top Rated Chester Hotels

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
$113 nightly
The price is $126 total per night
$126 total
May 24 - May 25
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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
16.75 mi from city center
$111 nightly
The price is $124 total per night
$124 total
May 25 - May 26
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 water dispenser, and a fireplace in the lobby.
Pet friendly
Parking included
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Free Cancellation
20.56 mi from city center
$88 nightly
The price is $100 total per night
$100 total
May 31 - Jun 1
Total with 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
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
19.08 mi from city center
$200 nightly
The price is $224 total per night
$224 total
May 18 - May 19
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
Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

2.5 out of 5
117 Conz St Northampton MA
Free Cancellation
18.2 mi from city center
$130 nightly
The price is $145 total per night
$145 total
May 20 - May 21
Total with taxes and fees
Quality Inn & Suites Northampton - Amherst features a gym, free WiFi in public areas, and a business center. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and luggage storage. Additional amenities include coffee/tea in a common area, a meeting room, and a computer station.
Breakfast included
Parking included
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
$188 nightly
The price is $210 total per night
$210 total
May 27 - May 28
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 dry cleaning/laundry, securing valuables, and concierge services. 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
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
$143 nightly
The price is $160 total per night
$160 total
Jun 2 - Jun 3
Total with taxes and fees
Guests of The Ellery enjoy access to free WiFi in public areas, coffee in a common area, and microwave in a common area. 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. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include express check-out, a fireplace in the lobby, and a water dispenser.
Breakfast included
Pet friendly
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr Chicopee MA
21.78 mi from city center
$103 nightly
The price is $117 total per night
$117 total
Jun 2 - Jun 3
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.
Pool
Breakfast included
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
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
May 25 - May 26
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
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
$127 nightly
The price is $146 total per night
$146 total
May 31 - Jun 1
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, luggage storage, and securing valuables. Additional amenities include a computer station, express check-out, and free newspapers.
Parking included
Free WiFi
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
16.94 mi from city center
$119 nightly
The price is $133 total per night
$133 total
May 25 - May 26
Total with taxes and fees
Guests staying at Hampton Inn & Suites Berkshires-Lenox enjoy an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls, an off-leash area, and litter boxes. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Breakfast included
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
15.06 mi from city center
$145 nightly
The price is $162 total per night
$162 total
May 18 - May 19
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
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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:

  • 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.
  • D. Hotel Suites & Spa is located 19.1 mi away, and this hotel has a full-service spa, 2 restaurants, and a fitness center.

Chester hotels essential information

Accommodation
871 hotels
Lowest Price
$100
Highest Price
$224
Popular hotels
Berkshire Mountain Lodge, Berkshires Untold, Quality Inn West Springfield, D. Hotel Suites & Spa, Quality Inn & Suites Northampton - Amherst, The Red Lion Inn, The Ellery, Tru by Hilton Chicopee Springfield, La Quinta Inn & Suites by Wyndham Springfield MA, Blue – A Modern Hotel, an Ascend Collection Hotel, Hampton Inn & Suites Berkshires-Lenox, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Recent Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

4/5 Good
"Loved this place - and would probably come. again. My only issue is that check-out is at 10:00 am. I had friends staying there who were not checking out, so I was able to linger in their suite. I imagine that I could have eaten breakfast in the large sunny open lounge on the first floor - if this is available to guests after check-out I suggest making that clear at check-in or on the description. I totally understand that they need time to clean rooms and since all of the rooms are suites. I may come again as a "remote work" vacation spot."
A verified traveler stayed at Berkshire Mountain Lodge
Posted 5 hours ago
Berkshire Mountain Lodge

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