Hotels in Chester
Search over 851 hotels from $103
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Top Rated Chester Hotels

D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Free Cancellation
Reserve now, pay when you stay
19.08 mi from city center
$121 nightly
The price is $135 total per night
$135 total
Feb 11 - Feb 12
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

Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
17.2 mi from city center
$121 nightly
The price is $136 total per night
$136 total
Mar 12 - Mar 13
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

The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
17.05 mi from city center
$93 nightly
The price is $103 total per night
$103 total
Feb 22 - Feb 23
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 tours or tickets, 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

Berkshires Untold
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
16.75 mi from city center
$98 nightly
The price is $110 total per night
$110 total
Mar 8 - Mar 9
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

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
Mar 1 - Mar 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 express check-out.
Pool
Air conditioning

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Free Cancellation
18.3 mi from city center
$102 nightly
The price is $114 total per night
$114 total
Mar 7 - Mar 8
Total with taxes and fees
Guests of Holiday Inn & Suites Pittsfield-Berkshires by IHG have access to an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, luggage storage, and tours or tickets. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly

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
$118 nightly
The price is $135 total per night
$135 total
Feb 19 - Feb 20
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 dry cleaning/laundry and securing valuables. Additional amenities include conference space, a 24-hour business center, and express check-in.
Pool
Parking included

Tru by Hilton Chicopee Springfield
440 Memorial Dr Chicopee MA
Free Cancellation
Reserve now, pay when you stay
21.78 mi from city center
$98 nightly
The price is $111 total per night
$111 total
Mar 2 - Mar 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.

The Red Lion Inn
30 Main Street Stockbridge MA
17.02 mi from city center
$183 nightly
The price is $205 total per night
$205 total
Mar 4 - Mar 5
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, securing valuables, and dry cleaning/laundry. Other amenities at this historic hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.

The Ellery
259 Elm Street Northampton MA
Free Cancellation
Reserve now, pay when you stay
17.28 mi from city center
$115 nightly
The price is $128 total per night
$128 total
Feb 26 - Feb 27
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

Fairfield Inn & Suites Springfield Northampton/Amherst
115A Conz Street Northampton MA
Free Cancellation
Reserve now, pay when you stay
18.16 mi from city center
$124 nightly
The price is $139 total per night
$139 total
Mar 1 - Mar 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 dry cleaning/laundry, luggage storage, and securing valuables. Additional amenities include meeting rooms, a business center, and coffee/tea in a common area.
Pool
Breakfast included

Residence Inn by Marriott West Springfield
64 Border Way West Springfield MA
Free Cancellation
Reserve now, pay when you stay
20.36 mi from city center
$116 nightly
The price is $133 total per night
$133 total
Feb 16 - Feb 17
Total with taxes and fees
Guests of Residence Inn by Marriott West Springfield enjoy an indoor pool, free WiFi in public areas, and a business center. Self parking is offered for USD 7 per day. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and securing valuables. Additional amenities include coffee/tea in a common area, free newspapers, and laundry facilities.
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.
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG is located 15.1 mi away, and this hotel has 2 indoor pools, 2 outdoor pools, and private balconies.
Close to central Chester, you'll find interesting places to visit like Chester Town Hall.
Chester hotels essential information
Accommodation | 851 hotels |
|---|---|
Lowest Price | $103 |
Highest Price | $205 |
Popular hotels | D. Hotel Suites & Spa, Berkshire Mountain Lodge, The Yankee, Trademark Collection by Wyndham, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Courtyard by Marriott West Springfield, Tru by Hilton Chicopee Springfield, The Red Lion Inn, The Ellery, Fairfield Inn & Suites Springfield Northampton/Amherst, Residence Inn by Marriott West Springfield |
Recent Reviews

Berkshires Untold
5/5 Excellent
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
A verified traveler stayed at Berkshires Untold
Posted 19 hours ago
More to Explore
- Hotels near Blandford Ski Area
- B&B in Blandford
- Hotels with Pool in Blandford
- Blandford Hotels
- Hotels near Otis Reservoir
- Hotels near Animagic Museum of Animation
- Hotels near Chesterfield Gorge
- Hotels near Chester Town Hall
- Tolland Hotels
- Hotels near Jacob's Pillow
- Hotels near Skyline Trail
- Inns in Washington
- 5 Star Hotels in Becket
- Farmstay in Becket
- Apartments in Becket
- Cabin Rentals in Becket
- Condo Rentals in Becket
- Cottages in Becket
- Guest Houses in Becket
- Beach Resorts & in Becket
- Cheap Hotels in Becket
- Kid Friendly Hotels in Becket
- Hotels with Pool in Becket
- Hotels with Restaurants in Becket
- Pet Friendly Hotels in Becket
- Romantic Getaways & Hotels in Becket
- Ski Resorts & in Becket
- Becket Hotels
- Lodges in Becket
- Motels in Becket
- Rv Parks in Becket
- Resorts in Becket
- 5 Star Hotels in Russell
- Cottages in Russell
- Inns in Russell
- Motels in Russell
- Apartments in Western Massachusetts
- Cabin Rentals in Western Massachusetts
- Cottages in Western Massachusetts
- Extended Stay Hotels in Western Massachusetts
- Boutique Hotels in Western Massachusetts
- Cheap Hotels in Western Massachusetts
- Kid Friendly Hotels in Western Massachusetts
- Golf Resorts & in Western Massachusetts
- Hotels with Hot Tubs in Western Massachusetts
- Romantic Getaways & Hotels in Western Massachusetts
- Spa Resorts & in Western Massachusetts
- Vacation Homes in Western Massachusetts
- Granville Hotels
- Hotels near Ashintully Gardens
- Hinsdale Hotels
- Southampton Hotels
- Monterey Hotels
- Hotels near Becket Land Trust Historic Quarry
- Hotels near Glendale Falls
- Hotels near Lee Premium Outlets
- B&B in Worthington
- Cottages in Worthington
- Guest Houses in Worthington
- Worthington Hotels
- Inns in Worthington
- Motels in Worthington
- Lee Hotels
- 5 Star Hotels in Norwich Lake
- Hotels near Littleville Lake
- Hotels near Berkshire Mountain Country Store
- Hotels near Bidwell House Museum
- Hotels near Otis Ridge
- The Berkshires Hotels
- Sandisfield Hotels
- 5 Star Hotels in Huntington
- Apartments in Huntington
- B&B in Huntington
- Cabin Rentals in Huntington
- Cottages in Huntington
- Inns in Huntington
- Vacation Homes in Huntington
- Middlefield Hotels
- Cummington Hotels
- Hotels near Pyramid Lake
- B&B in Otis
- Cabin Rentals in Otis
- Guest Houses in Otis
- Pet Friendly Hotels in Otis
- Otis Hotels
- Motels in Otis
- Vacation Homes in Otis
- Rv Parks in Otis
- Resorts in Otis



