Find Hotels with a Pool in Chesterfield, MA

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Check availability on Chesterfield Hotels with a Pool

Our top choices for Chesterfield hotels with a pool

Indoor pool, open 7:00 AM to 10:00 PM, sun loungers
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1001)
"Everything was perfect: clean room, great breakfast, courteous staff!"
United States
Tiffany
$87 nightly
The price is $99
Dec 22 - Dec 23
Total with taxes and fees
Tru by Hilton Chicopee Springfield
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
$108 nightly
The price is $121
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2246)
"Very nice property, very friendly and accommodating staff and the restaurant onsite is fabulous "
United States
Susan
$121 nightly
The price is $135
Dec 15 - Dec 16
Total with taxes and fees
D. Hotel Suites & Spa
Indoor pool
Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG
2.5 star property
West Springfield
8.4 out of 10, Very Good, (795)
"Staff are awesome"
United States
Sherry
$84 nightly
The price is $96
Dec 14 - Dec 15
Total with taxes and fees
Candlewood Suites West Springfield by IHG
Indoor pool
Hampton Inn Westfield

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (816)
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
$104 nightly
The price is $116
Jan 12 - Jan 13, 2026
Total with taxes and fees
Hampton Inn Westfield
Indoor pool
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (984)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$93 nightly
The price is $104
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield
3.0 star property
West Springfield
9.2 out of 10, Wonderful, (582)
"Room was clean and staff was super friendly "
United States
Jessuca
$118 nightly
The price is $135
Dec 14 - Dec 15
Total with taxes and fees
Courtyard by Marriott West Springfield
Seasonal outdoor pool
Hampton Inn West Springfield

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very Good, (1001)
"nearby eateries"
United States
Majorie
$95 nightly
The price is $109
Dec 18 - Dec 19
Total with taxes and fees
Hampton Inn West Springfield
Indoor pool
TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.8 out of 10, Exceptional, (57)
"The property is very clean and pet friendly. The staff were very friendly and professional. I will definitely stay here again."
United States
Diana
$149 nightly
The price is $166
Dec 18 - Dec 19
Total with taxes and fees
TownePlace Suites by Marriott Hadley Amherst
Indoor pool
Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
2.5 star property
Holyoke
9.2 out of 10, Wonderful, (593)
"Beds are super comfortable room was very clean"
United States
Lisa
$118 nightly
The price is $132
Dec 14 - Dec 15
Total with taxes and fees
Fairfield Inn & Suites Springfield Holyoke
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 Chesterfield Hotel Reviews

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Stayed 3 nights, really great hotel and value. "
Vince 3-night trip
Posted 5 hours ago
D. Hotel Suites & Spa

Frequently asked questions

What are some hotels with pools in Chesterfield?
D. Hotel Suites & Spa: Offers 2 restaurants, an indoor pool, and a full-service spa. Berkshire Mountain Lodge: Provides free self parking, an indoor pool, and complimentary wireless internet access. Quality Inn West Springfield: Features buffet, a seasonal outdoor pool, and free self parking. Comfort Inn & Suites: Hotel located near University of Massachusetts Amherst. Offers full, an indoor pool, and complimentary wired internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features a health club, an indoor pool, and complimentary wired internet access.
What is there to see and do in Chesterfield?
Spend some time experiencing the great outdoors at Chesterfield Gorge and Knightville Dam & Reservation. During your stay, check out sights such as Chesterfield Public Library, Westfield River, and Chesterfield Town Hall.
When is the best time to book a hotel with a pool in Chesterfield?
Taking into account the local weather in Chesterfield can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Chesterfield are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.

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