Title: Book the Best Hotels with POOL in Chesterfield in 2026 | Expedia.ca [Hotels in Chesterfield](https://expedia.ca/Chesterfield-Hotels.d89029.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.ca/Chesterfield-Vacation-Rentals.d89029.Travel-Guide-VacationRentals)[Chesterfield Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterfield.d89029.Car-Rental-Guide)[Chesterfield Vacation Packages](https://expedia.ca/Chesterfield.d89029.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chesterfield Hotels with a Pool Tonight [Mar 24 - Mar 25](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-03-24&endDate=2026-03-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 25 - Mar 26](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-03-25&endDate=2026-03-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-03-27&endDate=2026-03-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-04-03&endDate=2026-04-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesterfield hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/f1b53b76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/efe975c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive King Room](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/4ae0b464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### D. Hotel Suites & Spa [](https://www.expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) Holyoke 9.4/10 Exceptional (2,220 reviews) "This has become our company's preferred hotel for business trips to the Holyoke/Northampton area. It is clean, quiet, safe, convenient, and the breakfast is stellar." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander CA $150 CA $174 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/201806cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/6761ce21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/465e60d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Mountain Lodge [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) Pittsfield 9.0/10 Wonderful (885 reviews) "Very comfortable and very close to ski slope and restaurants" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frederick CA $125 CA $170 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/07d4dc21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/13980508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/w4000h2663x0y4-2923be4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/cb762de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Hadley Amherst [](https://www.expedia.ca/Hadley-Hotels-TownePlace-Suites-By-Marriott-Hadley-Amherst.h34260.Hotel-Information) Hadley 9.8/10 Exceptional (75 reviews) "Everything is great here and pet friendly :) " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan CA $209 CA $233 total includes taxes & fees Apr 8 - Apr 9 [](https://www.expedia.ca/Hadley-Hotels-TownePlace-Suites-By-Marriott-Hadley-Amherst.h34260.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/fc5fc5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Accessible, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/65617a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/c31a7f40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/683c1f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn West Springfield [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-West-Springfield.h21212.Hotel-Information) West Springfield 8.2/10 Very good (1,000 reviews) "Very good place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gloria CA $145 CA $166 total includes taxes & fees Apr 2 - Apr 3 [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-West-Springfield.h21212.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/5b7eab2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/4592453d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/2a79c048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/c682c6c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites Springfield Holyoke [](https://www.expedia.ca/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-Holyoke.h15914307.Hotel-Information) Holyoke 9.2/10 Wonderful (619 reviews) "staff is nice and kind" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wanjiang CA $162 CA $181 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-Holyoke.h15914307.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/41b28621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/a06cdca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/f0e51cc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/e6cbbcf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Hadley - Amherst [](https://www.expedia.ca/Springfield-Hotels-Comfort-Inn-Suites.h558078.Hotel-Information) Hadley 9.2/10 Wonderful (1,006 reviews) "We had a quick one night stay and found everything clean and the staff was attentive." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $164 CA $183 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Springfield-Hotels-Comfort-Inn-Suites.h558078.Hotel-Information) ![Indoor pool, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/a0205904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/40e8ece9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/f36d24b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/b9956cb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru by Hilton Chicopee Springfield [](https://www.expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) Chicopee 9.0/10 Wonderful (1,005 reviews) "Friendly clean accommodation were just what we needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carrie CA $145 CA $165 total includes taxes & fees Apr 2 - Apr 3 [](https://www.expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/35e3e6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Refrigerator](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/w4600h3096x0y4-086b73d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/eda0b159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/0d525668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Westfield [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-By-Hilton-Westfield.h2076197.Hotel-Information) Westfield 8.4/10 Very good (834 reviews) "Excelente " ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Angelica Enid Miranda CA $151 CA $168 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-By-Hilton-Westfield.h2076197.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/21075738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/e3cded0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/4626de59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/e43c1750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Creation Station is a cozy place so make yourself at home. [](https://www.expedia.ca/Easthampton-Hotels-The-Creation-Station-Is-A-Cozy-Place-So-Make-Yourself-At-Home.h34080135.Hotel-Information) Easthampton Ma. 10/10 Exceptional (75 reviews) "An amazing location with the most friendly host! My mom, dog and i absolutely enjoyed this spot. Perfect for a fall get away and would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly Z. CA $247 CA $385 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Easthampton-Hotels-The-Creation-Station-Is-A-Cozy-Place-So-Make-Yourself-At-Home.h34080135.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/dcc4e9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/67e1adab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w6714h4455x8y0-7f30ce4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w4000h2467x0y0-95fb3171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) Pittsfield 9.2/10 Wonderful (87 reviews) "Amazing stuff they went above and beyond to accommodate on fridge cold day, good breakfast, hot tub is amazing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paulo Eduardo CA $181 CA $202 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-04-07&endDate=2026-04-08®ionId=89029&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Chesterfield Breakfast included 4 stars 5 stars Hot tub Spa ## Top Chesterfield Hotel Reviews ![The Ellery](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/143e42a0_y.jpg) ### The Ellery 8/10 Good "Yes" [](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) ![Fairfield Inn & Suites Springfield Holyoke](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/2a79c048_y.jpg) ### Fairfield Inn & Suites Springfield Holyoke 10/10 Excellent "We enjoyed our 3 nights it was quiet and very clean " [](https://expedia.ca/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-Holyoke.h15914307.Hotel-Information) ![Candlewood Suites West Springfield by IHG](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/537cea4c_y.jpg) ### Candlewood Suites West Springfield by IHG 8/10 Good "The staff is friendly and helpful. " [](https://expedia.ca/Springfield-Hotels-Candlewood-Suites-West-Springfield.h897535.Hotel-Information) ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "The staff were very friendly, making the entire stay pleasant from check-in to check-out. The hotel was clean and well-maintained, and the surroundings were quiet, which made it easy to relax. The room was also quite spacious, providing plenty of comfort during the stay. It’s a great choice for anyone visiting Amherst, as the location is very convenient. " [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Courtyard by Marriott Hadley Amherst](https://images.trvl-media.com/lodging/2000000/1660000/1659000/1658945/978d1151_y.jpg) ### Courtyard by Marriott Hadley Amherst 6/10 Okay "Clean room. No conditioner in the shower and soap almost out. " [](https://expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-Hadley-Amherst.h1658945.Hotel-Information) ![Comfort Inn & Suites Hadley - Amherst](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/f0e51cc3_y.jpg) ### Comfort Inn & Suites Hadley - Amherst 8/10 Good "N/A" [](https://expedia.ca/Springfield-Hotels-Comfort-Inn-Suites.h558078.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Staff was pleasant! Clean and the restaurant was excellent!" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Quality Inn West Springfield](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/58b2bc45_y.jpg) ### Quality Inn West Springfield 10/10 Excellent "Clean, comfortable, and breakfast!" [](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ![Blue – A Modern Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/02a266b2_y.jpg) ### Blue – A Modern Hotel, an Ascend Collection Hotel 8/10 Good "Sketchy pulling in, old abandon place in front." [](https://expedia.ca/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Chesterfield? ### What is there to see and do in Chesterfield? ### When is the best time to book a hotel with a pool in Chesterfield? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Beach Hotel Hotels in Cambridge ](https://www.expedia.ca/Cambridge-Hotels-Beach-Hotel.0-0-d8093-tBeachHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Cambridge ](https://www.expedia.ca/Cambridge-Hotels-Couples-Resorts-Hotels.0-0-d8093-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Cambridge ](https://www.expedia.ca/Cambridge-Hotels-Hotel-With-Pool.0-0-d8093-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Winery Hotels in Cambridge ](https://www.expedia.ca/Cambridge-Hotels-Winery-Hotel.0-0-d8093-tWineryHotel.Travel-Guide-Filter-Hotels) - 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