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
$113 nightly
The price is $126 total per night
$126 total
Sep 28 - Sep 29
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

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
$119 nightly
The price is $135 total per night
$135 total
Oct 13 - Oct 14
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

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
$89 nightly
The price is $102 total per night
$102 total
Oct 8 - Oct 9
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 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

Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
20.56 mi from city center
$92 nightly
The price is $106 total per night
$106 total
Oct 8 - Oct 9
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
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
Oct 1 - Oct 2
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 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

Riverdale Inn
1500 Riverdale Street, On Route 5, 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
Sep 28 - Sep 29
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

Tru by Hilton Chicopee Springfield
440 Memorial Dr, Chicopee, MA
Free Cancellation
Reserve now, pay when you stay
21.84 mi from city center
$116 nightly
The price is $132 total per night
$132 total
Oct 12 - Oct 13
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, securing valuables, and luggage storage. Additional amenities include a 24-hour business center, an arcade/game room, and free newspapers.
Pool
Breakfast included

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free Cancellation
Reserve now, pay when you stay
15.06 mi from city center
$138 nightly
The price is $154 total per night
$154 total
Sep 28 - Sep 29
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 express check-out.

The Red Lion Inn
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
17.02 mi from city center
$219 nightly
The price is $245 total per night
$245 total
Sep 29 - Sep 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. The 24-hour front desk has multilingual staff ready to assist with securing valuables, 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.

Quality Inn & Suites Northampton - Amherst
117 Conz St, Northampton, MA
Free Cancellation
Reserve now, pay when you stay
18.2 mi from city center
$127 nightly
The price is $141 total per night
$141 total
Sep 29 - Sep 30
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

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
$149 nightly
The price is $170 total per night
$170 total
Sep 29 - Sep 30
Total with 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 securing valuables and dry cleaning/laundry. Additional amenities include conference space, a 24-hour business center, and express check-in.
Pool
Parking included

Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
16.75 mi from city center
$128 nightly
The price is $143 total per night
$143 total
Sep 29 - Sep 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.
Pet friendly
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:
- Berkshire Mountain Lodge is located 17.2 mi away, and this lodge has free WiFi, free parking, and in-room kitchens.
- 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.
- Red Roof Inn PLUS+ West Springfield is located 20.5 mi away, and this hotel has free WiFi, free parking, and comfy beds.
Close to central Chester, you'll find interesting places to visit like Chester Town Hall.
Chester hotels essential information
Accommodation | 828 hotels |
---|---|
Lowest Price | $102 |
Highest Price | $245 |
Popular hotels | Berkshire Mountain Lodge, La Quinta Inn & Suites by Wyndham Springfield MA, Red Roof Inn PLUS+ West Springfield, Quality Inn West Springfield, D. Hotel Suites & Spa, Riverdale Inn, Tru by Hilton Chicopee Springfield, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Red Lion Inn, Quality Inn & Suites Northampton - Amherst, Courtyard by Marriott West Springfield, Berkshires Untold |
Recent Reviews

Berkshire Mountain Lodge
5/5 Excellent
"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again. "
A verified traveler from Weymouth stayed at Berkshire Mountain Lodge
Posted 2 days ago