Title: Chester Vacation Home Rentals from CA $498: 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) ![](https://mediaim.expedia.com/destination/2/5376b74ed08fb0cd0348035ae5ca74c9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Elizabeth Massa Peroulakis # Chester Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-10-10&endDate=2025-10-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Vacation Homes ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/a5ddb496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/85b23873.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/89102e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/63cb703a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table Pittsfield 9.8/10 Exceptional (148) "We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved." [](https://www.expedia.ca/Pittsfield-Hotels-Beautiful-8-Bedroom.h33492239.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94720000/94712400/94712371/48ff3e72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/95000000/94720000/94712400/94712371/026f0762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94720000/94712400/94712371/a7563638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, desk, free WiFi](https://images.trvl-media.com/lodging/95000000/94720000/94712400/94712371/ccb30f95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old World Charm, Modern Conveniences - 3 BR private home in quiet setting Easthampton 10/10 Exceptional (24) "This beautiful home was perfect for our short stay in Western Massachusetts. Everything was just lovely, clean, comfortable, quiet. Great hosts and so kind and accommodating to our needs. Thank you so much. We will definitely look to stay here again for future family visits. " [](https://www.expedia.ca/Easthampton-Hotels-Private-HomeOld-World-Charm.h94712371.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/34000000/33710000/33704200/33704131/0d5d0135.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33704200/33704131/d2474d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33704200/33704131/8aad64c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33704200/33704131/ae89362d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stockbridge Village in Summer Stockbridge 9.0/10 Wonderful (18) "This is a great home within walking distance of the interesting town of Stockbridge. The place is well equipped and has a charm consistent of what you can expect for a historic farm house. We would stay here again." [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Village-In-Summer.h33704131.Hotel-Information) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/636f9a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, dishwasher](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/8b34823f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/378fd21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/d06b32cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5-bedroom house in charming Lee with WiFi Lee CA $627 CA $1,144 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/02c7301e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/960bf7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/a366bf74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/e175fcb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amore Estate - beautiful room with many places to explore and relax in. Lenox 9.0/10 Wonderful (29) "Beautiful, spacious house in a great location!" [](https://www.expedia.ca/Lenox-Hotels-October-Mountain-Escape.h91593496.Hotel-Information) ![Fireplace, books](https://images.trvl-media.com/lodging/33000000/32740000/32734000/32733978/606953af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32740000/32734000/32733978/bc5f9f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32740000/32734000/32733978/4166b2dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32740000/32734000/32733978/81e69b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest Cummington 9.6/10 Exceptional (37) "My friends and I had the most beautiful rainy weekend here to celebrate my 40th birthday. The spot was perfect for the 5 of us and the river was such a wonderful bonus to our peaceful trip!" [](https://www.expedia.ca/Cummington-Hotels-Beautiful-3BR-River-View.h32733978.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/65000000/64150000/64145900/64145854/3d8d954d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64150000/64145900/64145854/1e9190a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/65000000/64150000/64145900/64145854/4034ab20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64150000/64145900/64145854/3e04c670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location Lanesborough 9.6/10 Exceptional (72) "Beautiful house and location that was perfect for a family weekend. Would 100% recommend!" [](https://www.expedia.ca/Lanesborough-Hotels-Wildlife-Cottage-By-The-Lake.h64145854.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/2ae49251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/95ce4320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/afeca776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/d0befd42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### General Williams Estate House Lenox/Stockbridge Stockbridge 9.8/10 Exceptional (110) "The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot." [](https://www.expedia.ca/General-Williams-Estate-House-LenoxStockbridge.h33509020.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/1993f238.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/145ce996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/w2439h1242x124y0-c2be86b7.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! Stockbridge 10/10 Exceptional (25) "We had a wonderful time in this home. It accommodated our family of 4 easily. Several of us had to work the first day there and there were ample quiet spots and quality wifi for us. So easy to walk to town to restaurants etc" [](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69770000/69763300/69763258/bf60ebb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69770000/69763300/69763258/07ea0eda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69770000/69763300/69763258/92cb5f01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/70000000/69770000/69763300/69763258/af8950e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hearts Desire is a furnished whole house in a small, colorful garden center. Lanesborough 10/10 Exceptional (93) "This was our third time at this property. We still love it and look forward to returning again." [](https://www.expedia.ca/Lanesborough-Hotels-Hearts-Desire-Is-A-Furnished-Whole-House-In-A-Small.h69763258.Hotel-Information) ![Lake](https://images.trvl-media.com/lodging/19000000/18770000/18761000/18760908/8493ce06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/19000000/18770000/18761000/18760908/2a49e9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/19000000/18770000/18761000/18760908/786e1f41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/19000000/18770000/18761000/18760908/b603a1ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++ Lenox 9.4/10 Exceptional (60) "I had such a great stay with a bunch of friends at the Fox Hollow Estate. The house is exactly as described, and very spacious. At no point did I ever feel packed into the house, there are so many activities that you can do around the area. If you're visiting for foliage, the property has wonderful viewpoints and is within a close 20 or less minute drive to the best views. I would gladly stay at the place again if I was in the area." [](https://www.expedia.ca/Lenox-Hotels-Luxury-Fox-Hollow-Estate-Home-On-Laurel-Lake-Dream-Location.h18760908.Hotel-Information) ![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/be941bed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/9e7f1a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/d795e81b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/13f97fa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut! Great Barrington 10/10 Exceptional (27) "Spacious, welcoming, so well stocked, we felt lucky to find the property." [](https://www.expedia.ca/Great-Barrington-Hotels-Minutes-From-Ski-Butternut.h78701034.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34010000/34008000/34007913/2800c888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/35000000/34010000/34008000/34007913/2cd290f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34008000/34007913/b0c97427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34010000/34008000/34007913/03d7dde0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Enjoy comfortable elegance in this secluded grand home located in town Lenox 10/10 Exceptional (73) "Great location for access to both Tanglewood and Lenox center. " [](https://www.expedia.ca/Lenox-Hotels-Enjoy-Comfortable-Elegance-In-This-Secluded-Grand-Home-Located-In-Town.h34007913.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) ![Exterior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/0e82b119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/508c5b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/af5c0679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Big farmhouse in the foothills of the Berkshires Russell 10/10 Exceptional (140) "Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!" CA $279 CA $498 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/78000000/77190000/77189600/77189557/w905h683x60y0-9a0589c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/78000000/77190000/77189600/77189557/c79d7de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/78000000/77190000/77189600/77189557/21a80444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/78000000/77190000/77189600/77189557/e20a0740.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Meadows House @ Otis Ridge w/ 7-person hot tub Otis 9.6/10 Exceptional (37) "We had a lovely time. Peaceful and cozy house, great private hot tub" [](https://www.expedia.ca/Otis-Hotels-The-Meadows-House-Otis-Ridge-W-7-Person-Hot-Tub.h77189557.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/222fc9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/10587e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/9a679a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, music library](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/0152068c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Grand property in Historic Stockbridge Stockbridge 10/10 Exceptional (102) "The Taggart House was a wonderful place to gather with friends and family to celebrate my birthday. The house is beautiful; the rooms are large; kitchen is great; bugs kept us from hanging out in the backyard but the conservatory was light and bright and a perfect spot for cocktails. We loved the proximity to the town of Stockbridge and we would walk back and forth a couple times a day. We had a couple of small issues, and Caitlin was very responsive in answering my questions/concerns. All in... [](https://www.expedia.ca/Stockbridge-Hotels-A-Grand-Estate-In-Historic-Stockbridge.h33960335.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29640000/29631700/29631677/21fd7b1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29640000/29631700/29631677/43b676df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/30000000/29640000/29631700/29631677/w1409h929x0y11-871fbc5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29640000/29631700/29631677/d3cf9fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Linny's Lakeview Cottage - Cozy, fun & updated Southwick 10/10 Exceptional (63) "Very great location, close to my family. Great spot!!" [](https://www.expedia.ca/Springfield-Hotels-Fully-Renovated-Lakeview-Cottage.h29631677.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114150000/114146500/114146475/530b7b48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/115000000/114150000/114146500/114146475/44d29ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/115000000/114150000/114146500/114146475/f2396fec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114150000/114146500/114146475/7b7a2a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Williams House 2-bedroom downtown Northampton with AC, WiFi Northampton 10/10 Exceptional (2) "Great location & unique charming place!" [](https://www.expedia.ca/Northampton-Hotels-Historic-Williams-House-2-Bedroom-Downtown-Northampton-With-AC.h114146475.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/51000000/50650000/50648800/50648773/90-3f5642cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/51000000/50650000/50648800/50648773/8adf5169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/51000000/50650000/50648800/50648773/30e3ed6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/51000000/50650000/50648800/50648773/461765c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stockbridge Village Cottage With Mountain View’s and walk to town Stockbridge 9.8/10 Exceptional (63) "Perfect long weekend with family at this lovely home!" [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Village-Cottage-With-Mountain-Views-And-Walk-To-Town.h50648773.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/63595554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/62b3ce52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/35eff0e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/eccd60b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country Stockbridge 10/10 Exceptional (128) "Close to Lenox and Stockbridge, lots to do. Beautiful yard and comfortable home. We had a great time and would definitely return to this house." [](https://www.expedia.ca/West-Stockbridge-Hotels-Location-Location-Berkshire-Glamour.h33932760.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=2025-10-17&endDate=2025-10-18®ionId=6005399&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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 ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Great place! Food excellent ss well!" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Tru by Hilton Chicopee Springfield](//images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/2bcbba21_y.jpg) ### Tru by Hilton Chicopee Springfield 10/10 Excellent "Pleasant stay" [](https://expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) ![Quality Inn West Springfield](//images.trvl-media.com/lodging/1000000/10000/7500/7486/7f7ace74_y.jpg) ### Quality Inn West Springfield 10/10 Excellent "Clean place " [](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ![D. Hotel Suites & Spa](//images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "Hotel is nice and rooms are nice. They could use some updating of the furniture in the room I stayed at but overall a nice place with a nice breakfast included " [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Quality Inn Chicopee - Springfield](//images.trvl-media.com/lodging/1000000/860000/856300/856259/4454c273_y.jpg) ### Quality Inn Chicopee - Springfield 10/10 Excellent "The staff was very friendly and professional. Rooms are very clean and quiet. Will definitely stay again." [](https://expedia.ca/Springfield-Hotels-Quality-Inn-Chicopee-Springfield.h856259.Hotel-Information) ![Baldwin Inn & Suites, SureStay Collection by Best Western](//images.trvl-media.com/lodging/1000000/20000/15800/15705/43807f20_y.jpg) ### Baldwin Inn & Suites, SureStay Collection by Best Western 10/10 Excellent "We stayed here when we went to an event at the eastern states exposition. It was coles, by so we were able to walk from the hotel to the fairgrounds" [](https://expedia.ca/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information) ![Courtyard by Marriott West Springfield](//images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/90293a2b_y.jpg) ### Courtyard by Marriott West Springfield 10/10 Excellent "Ryan at front desk was friendly and courteous over the phone and upon arrival! " [](https://expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information) ![The Ellery](//images.trvl-media.com/lodging/1000000/900000/892700/892654/0b76727c_y.jpg) ### The Ellery 10/10 Excellent "Great stay" [](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "The staff was helpful, friendly. Nice location. The room was very clean and quiet, but so much of the place is brown. Brown carpet, brown paneled walls, brown chair, brown furniture, brown lamps. A minor detraction, but I look at hotel decor with a discerning eye and I like things to be less bland/mundane." [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ## Find out more about Chester ## Chester Vacation Homes information | Number of reviews | 1,034 | | --- | --- | | Accommodation | 280 Vacation Homes | | Lowest Price | CA $498 | | Highest Price | CA $1,144 | ## 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) - [Chalets in Becket](https://www.expedia.ca/Becket-Chalets.d6005395-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Becket](https://www.expedia.ca/Becket-Guest-Houses.d6005395-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Becket](https://www.expedia.ca/Becket-Hotels-Cheap-Hotels.0-0-d6005395-tCheapHotels.Travel-Guide-Filter-Hotels) - 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