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 [Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-02-06&endDate=2026-02-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 7 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-02-07&endDate=2026-02-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-02-06&endDate=2026-02-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-02-13&endDate=2026-02-15&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/1000000/10000/2100/2067/91284a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a97806ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) Pittsfield 8.0/10 Very good (1,001 reviews) "Staff was very courteous and rooms clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $140 CA $156 total includes taxes & fees Mar 7 - Mar 8 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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/dffd5115.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 (1,003 reviews) "Friendly clean accommodation were just what we needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carrie CA $133 CA $151 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/b1dcd87b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/e036973a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/dc02db60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/ab501d5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites West Springfield by IHG [](https://www.expedia.ca/Springfield-Hotels-Candlewood-Suites-West-Springfield.h897535.Hotel-Information) West Springfield 8.4/10 Very good (836 reviews) "Nice staff clean room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Damian CA $108 CA $124 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Springfield-Hotels-Candlewood-Suites-West-Springfield.h897535.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) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/d26efba1.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/c31a7f40.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 $102 CA $117 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-West-Springfield.h21212.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) ![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/a06cdca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/d1319a54.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 (1,005 reviews) "Very clean rooms, comfy bed, decent breakfast in the morning. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda CA $153 CA $171 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Springfield-Hotels-Comfort-Inn-Suites.h558078.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34.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 9.2/10 Wonderful (2,238 reviews) "Great service, clean & quiet rooms, and a solid breakfast to start the day" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie CA $141 CA $164 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/5c3a2624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/8c645106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/90293a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/eaa5d51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott West Springfield [](https://www.expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information) West Springfield 9.2/10 Wonderful (597 reviews) "Nice and very clean hotel ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Morgan CA $162 CA $185 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.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) ![Property amenity](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/d0f01d8b.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) ![Snack bar](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/4592453d.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 (608 reviews) "Room was spotless, staff were nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose I Medina CA $161 CA $180 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-Holyoke.h15914307.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/w696h390x1y0-dec65b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/27ba18f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/b6081d93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/bba60f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Lenox Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) Pittsfield 9.2/10 Wonderful (665 reviews) " Nice staff - beautiful hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARY CA $186 CA $208 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/60000/50500/50480/1b5466c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50500/50480/e190a2f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/60000/50500/50480/750b55e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/60000/50500/50480/894ab711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites West Springfield [](https://www.expedia.ca/Springfield-Hotels-Comfort-Inn-Suites.h50480.Hotel-Information) West Springfield 7.6/10 Good (913 reviews) "Very helpful staff, comfy beds! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $146 CA $167 total includes taxes & fees Feb 21 - Feb 22 [](https://www.expedia.ca/Springfield-Hotels-Comfort-Inn-Suites.h50480.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=2026-02-20&endDate=2026-02-21®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 Ocean view 5 stars Hot tub ## Top Chesterfield Hotel Reviews ![Hotel UMass](https://images.trvl-media.com/lodging/1000000/490000/480800/480785/4e423f91_y.jpg) ### Hotel UMass 10/10 Excellent "Great " [](https://expedia.ca/Springfield-Hotels-Hotel-UMass.h480785.Hotel-Information) ![Fairfield Inn & Suites Springfield Northampton/Amherst](https://images.trvl-media.com/lodging/9000000/8450000/8449800/8449737/e6abed3c_y.jpg) ### Fairfield Inn & Suites Springfield Northampton/Amherst 10/10 Excellent "Gorgeous room amazing stay" [](https://expedia.ca/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-NorthamptonAmherst.h8449737.Hotel-Information) ![Quality Inn & Suites Northampton - Amherst](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/f86e1269_y.jpg) ### Quality Inn & Suites Northampton - Amherst 10/10 Excellent "Great room, very clean and welcoming, helpful staff. Breakfast was pretty good too!" [](https://expedia.ca/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.Hotel-Information) ![Comfort Inn & Suites](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/d1319a54_y.jpg) ### Comfort Inn & Suites 10/10 Excellent "Clean room, friendly staff, " [](https://expedia.ca/Springfield-Hotels-Comfort-Inn-Suites.h558078.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 10/10 Excellent "Great hotel to stay in. Staff is super friendly and pays attention to a details. Rooms are kept fresh and clean. I will return in future" [](https://expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-Hadley-Amherst.h1658945.Hotel-Information) ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "Clean, cozy on a very cold night! Breakfast had a good variety and staff was pleasant. Will definitely go back " [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b_y.jpg) ### Red Roof Inn PLUS+ South Deerfield – Amherst 10/10 Excellent "All good. Strange stay as there was a large storm approaching." [](https://expedia.ca/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) ![The Ellery](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/0b76727c_y.jpg) ### The Ellery 10/10 Excellent "Comfortable room, great breakfast with cozy fireplace. Friendly and efficient staff. Easy parking. Walkable area amidst Smith College and fifteen minute walk to downtown Northampton attractions and restaurants. " [](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.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 10/10 Excellent "great room . wish they had better breakfast " [](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) - 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