Title: Chester Vacation Home Rentals from CA $383: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6005399.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6005399.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6005399.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6005399.Destination-Travel-Guides) ![An amazing keystone arch bridge!](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Chris Addams ![](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.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 prices for these dates In two weeks [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester vacation homes ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111950000/111942700/111942669/3219fa05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111950000/111942700/111942669/d1d1a287_edited_5b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111950000/111942700/111942669/1b404b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/112000000/111950000/111942700/111942669/dead818f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Home in Holyoke with 3 bedrooms [](https://www.expedia.ca/Holyoke-Hotels-Cozy-Home-In-Holyoke-With-2-Bedrooms.h111942669.Hotel-Information) Holyoke 9.8/10 Exceptional (14 reviews) "Very neat and clean. Decorated for Fall, which was nice. All amenities made for a really nice time." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacy G. CA $178 CA $452 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Holyoke-Hotels-Cozy-Home-In-Holyoke-With-2-Bedrooms.h111942669.Hotel-Information) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110170000/110169900/110169858/d5a3643f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110170000/110169900/110169858/4b576c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110170000/110169900/110169858/e597dbad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110170000/110169900/110169858/6f0714e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Townhouse with Pool Table - Renovated w/ King Bed [](https://www.expedia.ca/Chicopee-Hotels-Townhouse-With-Pool-Table-Renovated-W-King-Bed.h110169858.Hotel-Information) Chicopee 10/10 Exceptional (12 reviews) "Perfect stay for a family. Enjoyed the pool table. Beds were comfortable. Showers were perfect. Beautifully decorated. We felt right at home. Would definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tonya Z. CA $246 CA $526 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Chicopee-Hotels-Townhouse-With-Pool-Table-Renovated-W-King-Bed.h110169858.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/123000000/122420000/122414000/122413946/w1318h869x1y0-41846b87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122420000/122414000/122413946/w1318h874x1y9-cd7269f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/123000000/122420000/122414000/122413946/w1318h872x1y0-9cb07866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/123000000/122420000/122414000/122413946/w1316h879x2y3-65b770cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Welcoming 3-bedroom house- Gardner home [](https://www.expedia.ca/Chicopee-Hotels-Welcoming-3-Bedroom-House-Gardner-Home.h122413946.Hotel-Information) Chicopee 10/10 Exceptional (1 review) "Overall had a great stay, the space is cozy and welcoming." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gracie B. CA $205 CA $529 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Chicopee-Hotels-Welcoming-3-Bedroom-House-Gardner-Home.h122413946.Hotel-Information) ![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/4626de59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/08d859c6.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) ![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 (73 reviews) "The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Connie P. CA $246 CA $383 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Easthampton-Hotels-The-Creation-Station-Is-A-Cozy-Place-So-Make-Yourself-At-Home.h34080135.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/dba15cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/8c55822c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/2281e60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/4e64ac0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine [](https://www.expedia.ca/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information) Sherwood Forest 9.8/10 Exceptional (11 reviews) "Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew F. CA $219 CA $540 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/cd1323be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/621adf1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/d3c8327e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/412632db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun Filled Lenox Retreat - Minutes to Tanglewood! [](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information) Lee 9.6/10 Exceptional (4 reviews) "The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah D. CA $246 CA $626 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/7377fc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/b924c628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/0f27818f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/f63afa55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Big farmhouse in the foothills of the Berkshires [](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information) Russell 10/10 Exceptional (143 reviews) "Perfect spot for a family celebration!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerry P. CA $201 CA $414 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/055ed8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, electric kettle](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/52345b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Ski Getaway in the Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) Great Barrington 9.2/10 Wonderful (9 reviews) "Close to a great bakery and near to a farm market and shopping mall. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cristine C. CA $277 CA $407 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/w2439h1242x124y0-c2be86b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b7940a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/d970b68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/9046d578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk into town, soak up sun on enclosed porch & steps away from nature trails! [](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) Stockbridge 10/10 Exceptional (33 reviews) "A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) cathy c. CA $409 CA $889 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/f9227a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/411deb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/079bb1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/3bbdf637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-bedroom house in beautiful Berkshires, close to amenities! [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information) Pittsfield CA $254 CA $427 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/bdc7550f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/a38bbe4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/44aa4835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/811d3663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions! [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) Pittsfield 7.8/10 Good (7 reviews) "The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liz V. CA $368 CA $677 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/125000000/124370000/124366500/124366451/19d8b324.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124370000/124366500/124366451/6e2041a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/125000000/124370000/124366500/124366451/3b1fbe78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124370000/124366500/124366451/5ec4e5d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King Bed w/ Game Room near Massmutual w/ Riverview [](https://www.expedia.ca/Chicopee-Hotels-King-Bed-W-Game-Room-Near-Massmutual-W-Riverview.h124366451.Hotel-Information) Chicopee CA $427 CA $828 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Chicopee-Hotels-King-Bed-W-Game-Room-Near-Massmutual-W-Riverview.h124366451.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/8b34823f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/9510eac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/17bd9585.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/b9c0be0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5-bedroom house in charming Lee with WiFi [](https://www.expedia.ca/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information) Lee 8.8/10 Excellent (3 reviews) "House was clean and made our Thanksgiving great with it's size and amenities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Khalil S. CA $650 CA $1,178 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/528fbc22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/a296b140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/d9eeb6ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/1c2ae12d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket. [](https://www.expedia.ca/Becket-Hotels-Secluded-Sophistication-In-The-Berkshires-49-Acres-Of-Quiet-Luxury-In-Becket.h120275326.Hotel-Information) Becket CA $458 CA $843 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Becket-Hotels-Secluded-Sophistication-In-The-Berkshires-49-Acres-Of-Quiet-Luxury-In-Becket.h120275326.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=2026-02-23&endDate=2026-02-24®ionId=6005399&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=APARTMENT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VILLA) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CABIN) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CONDO) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VACATION_HOME) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Private-Vacation-Homes.d6005399-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Private-Vacation-Homes.d6005399-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Residence Inn by Marriott West Springfield](https://images.trvl-media.com/lodging/1000000/860000/852800/852716/fb4f9524_y.jpg) ### Residence Inn by Marriott West Springfield 10/10 Excellent "Great friendly helpful staff, clean room and amenities " [](https://expedia.ca/Springfield-Hotels-Residence-Inn-By-Marriott-West-Springfield.h852716.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, safe, quiet, and comfortable. Fantastic full breakfast as always." [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Only stayed for 1 night but was very impressed with this property. The room was very clean and spacious. Bed was comfortable as well. Had my two kids with me so the pool and hot tub was an amazing amenity. Left early in the morning to ski so the stay was short, but would’ve loved to stay longer and will definitely look to return to this property in the future. " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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 "Rooms were clean and spacious. Our room had 2 queen beds and they easily accommodated 2 of us and our late teen children. It's only 20 minutes from Jiminy Peak skiing area. There are several breakfast and food places nearby. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "loved " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.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) ![Tru by Hilton Chicopee Springfield](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/2bcbba21_y.jpg) ### Tru by Hilton Chicopee Springfield 10/10 Excellent "Friendly clean accommodation were just what we needed. " [](https://expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Springfield MA](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/71c77a60_y.jpg) ### La Quinta Inn & Suites by Wyndham Springfield MA 10/10 Excellent "I had a great night of sleep" [](https://expedia.ca/Springfield-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Springfield-MA.h18056.Hotel-Information) ## Find out more about Chester ## Chester Vacation Homes information | Number of reviews | 305 | | ----------------- | ------------------ | | Accommodation | 263 Vacation Homes | | Lowest Price | CA $383 | | Highest Price | CA $1,178 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Otis ](https://www.expedia.ca/3Star-Otis-Hotels.s30-0-d6005412.Travel-Guide-Filter-Hotels) - [B&B in Becket ](https://www.expedia.ca/Becket-Bed-And-Breakfast.d6005395-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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