Photo by Elizabeth Massa Peroulakis

Find Hotels with a Pool in Chester, MA

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Check availability on Chester Hotels with a Pool

Top Chester Hotels with a Pool

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (674)
"Great place to have a girls night for old friends when one of us is back in town for a night. Very convenient place well kept. "
$103 nightly
The price is $115
Nov 10 - Nov 11
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Element Lenox Berkshires
Indoor pool
Element Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (5)
"New hotel very nice"
$135 nightly
The price is $151
Nov 9 - Nov 10
Total with taxes and fees
Element Lenox Berkshires
D. Hotel Suites & Spa
Indoor pool
D. Hotel Suites & Spa
3.0 star property
9.4 out of 10, Exceptional, (2238)
"The staff is wonderful both at the hotel and dining ! "
$134 nightly
The price is $150
Oct 22 - Oct 23
Total with taxes and fees
D. Hotel Suites & Spa
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (898)
"Excellent customer service and great rooms"
$103 nightly
The price is $115
Nov 2 - Nov 3
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Candlewood Suites West Springfield by IHG
Indoor pool
Candlewood Suites West Springfield by IHG
2.5 star property
8.4 out of 10, Very Good, (771)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
$98 nightly
The price is $112
Oct 26 - Oct 27
Total with taxes and fees
Candlewood Suites West Springfield by IHG
Tru by Hilton Chicopee Springfield
Indoor pool, open 7:00 AM to 10:00 PM, sun loungers
Tru by Hilton Chicopee Springfield
2.5 star property
8.8 out of 10, Excellent, (1010)
" Staff was wonderful and hotel was spotless. Great breakfast also!"
$102 nightly
The price is $115
Nov 11 - Nov 12
Total with taxes and fees
Tru by Hilton Chicopee Springfield
Howard Johnson by Wyndham Lenox
Exterior
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (809)
"Good for the one night drive through! "
$79 nightly
The price is $88
Oct 19 - Oct 20
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Hampton Inn West Springfield
Seasonal outdoor pool
Hampton Inn West Springfield
2.5 star property
8.2 out of 10, Very Good, (1007)
"Will visit again "
$114 nightly
The price is $130
Nov 12 - Nov 13
Total with taxes and fees
Hampton Inn West Springfield
TownePlace Suites by Marriott Hadley Amherst
Indoor pool
TownePlace Suites by Marriott Hadley Amherst
3.0 star property
9.8 out of 10, Exceptional, (46)
"Nicely groomed "
$175 nightly
The price is $196
Nov 10 - Nov 11
Total with taxes and fees
TownePlace Suites by Marriott Hadley Amherst
Berkshire Mountain Lodge
Indoor pool
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (698)
"Great stay, perfect "
$106 nightly
The price is $118
Nov 3 - Nov 4
Total with taxes and fees
Berkshire Mountain Lodge
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.
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Top Chester Hotel Reviews

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Beautiful stay! Great restaurant, great pool/hot tub/ breakfast on the patio! "
Michelle 1-night trip
Posted 1 day ago
D. Hotel Suites & Spa

Frequently asked questions

What are some accommodations with pools in Chester?
La Quinta Inn & Suites by Wyndham Springfield MA: Hotel located near MGM Springfield. Features a snack bar/deli, an indoor pool, and buffet. Red Roof Inn PLUS+ West Springfield: Provides free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Hotel located near Big E. Features buffet, a seasonal outdoor pool, and free self parking. Quality Inn West Springfield: Features 2 restaurants, an indoor pool, and a full-service spa. Riverdale Inn: Offers a snack bar/deli, an indoor pool, and daily.
What is there to see and do in Chester?
Make a point to visit attractions like Ashintully Gardens and The Bookstore. Discover sights such as Chester Town Hall during your stay.
When is the best time to book a hotel with a pool in Chester?
Taking into account the local weather in Chester is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.

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