Title: Top Cheshire Cabin Rentals | Expedia.ca [Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d6005398.Travel-Guide-VacationRentals)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.ca/Cheshire.d6005398.Destination-Travel-Guides) ![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Cabins in Cheshire for Rent from CA $254 - ![](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 Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cheshire cabin rentals ![Exterior detail](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/a78d5e6a_edited_6c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/02d3bd96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/d249528d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/78f91337.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Sand Lake 10/10 Exceptional (13) "Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanna R. CA $173 CA $255 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Sand-Lake-Hotels-Cabin-In-The-Woods.h101301745.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/ec8e2057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/137726e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/edecce8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/0ab9f2e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Hinsdale 9.8/10 Exceptional (34) "Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lindsey E. CA $247 CA $608 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/072199c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/3f3d1749.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/fe676105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/e67896be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Stephentown 7.0/10 Good (2) "It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bill B. CA $182 CA $402 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Stephentown-Hotels-Charming-3-Bedroom-Cabin-For-Nature-Lovers.h112619076.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102620000/102613300/102613211/ba127977.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102620000/102613300/102613211/2c6abeb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102620000/102613300/102613211/d7345ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102620000/102613300/102613211/197da850.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Sand Lake 10/10 Exceptional (1) "The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Georgia M. CA $173 CA $254 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Sand-Lake-Hotels-Taborton-Harvest-Timber-TrailsUnique-Cabin-Experience.h102613211.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/w1024h593x0y45-2966e99d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/730ec918.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/4fcb5611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/w508h683x258y0-18d1cb27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Charlemont 10/10 Exceptional (43) "We enjoyed our stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hillary S. CA $554 CA $829 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Charlemont-Hotels-Bear-Creek-Cabin.h91621591.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93410000/93401900/93401870/e6030a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93410000/93401900/93401870/4fa6909a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93410000/93401900/93401870/c7323063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93410000/93401900/93401870/c2b10b31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Averill Park 10/10 Exceptional (3) "Our family had a great weekend get-away at the Lake House! Thank you for the kind special touches, such as the milk and eggs from June Farm. The lake access and screened in porch were huge hits with everyone." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea N. CA $890 CA $1,590 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Averill-Park-Hotels-A-Spectacularly-Charming-LAKE-HOUSE-On-Gorgeous-Burden-Lake.h93401870.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=2025-12-24&endDate=2025-12-25®ionId=6005398&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%2FCheshire-Cabins.d6005398-aaCabins.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Cabins.d6005398-aaCabins.Travel-Guide-Accommodation) ## Top Cheshire Hotel Reviews ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Excellent stay, nice, clean 2 bedroom Villa, staff excellent, amenities excellent, great location would definitely stay again " [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 10/10 Excellent "Comfortable, quiet, clean, great breakfast " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick. " [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.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 "Great staff especially Katherine " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Spacious rooms. Attentive staff. Free parking behind the hotel." [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "I don’t have a single complaint about this hotel! Everything was perfect! Staff was great, parking was easy, everything was clean! My family and I will definitely be staying here again in the future! " [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "My room was so big! Very clean, huge bathroom, claw foot tub. Highly recommend this place. It had a great vibe. Was not industrial like a hotel, had a very clean and comforting feeling, like you were visiting a relative. I stayed here for my brother’s wedding at MoCA. Great experience all around. Definitely will be back. " [](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "It was all well cared for." [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "I am a cross country traveling nurse. The Berkshire Mountain Lodge was perfect for my needs. A fully functioning well appointed kitchen. Spacious living quarters with excellent views. The best water pressure on a shower that I have ever known. Fantastic after a long day of work or out hiking the many nature trails here. And the bed was so perfectly firm and cozy that I drifted effortlessly to sleep. The grounds, the amenities and the coordinated activities to bring you together in community made me feel included. Definitely a place I will continue to return to for many years." [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ## Find out more about Cheshire ## Cheshire Cabin Rentals information | Number of reviews | 92 | | ----------------- | ---------------- | | Accommodation | 26 Cabin Rentals | | Lowest Price | CA $254 | | Highest Price | CA $1,590 | ## Frequently asked questions ### What are the best cabins near Cheshire? ### Are there cheap cabins in Cheshire? ### What are the best mountain cabins near Cheshire? ### What are the best river cabins near Cheshire? ### What are the best cabins with pools near Cheshire? ### Can I find beach cabins near Cheshire? ### What are the best weekend cabin rentals in Cheshire? ### What are the best cabin prices in Cheshire? ### Can I find log cabins in Cheshire? ### What are the highest-rated cabins in Cheshire? ### Why should I book a cabin in Cheshire? ### What are the top nature cabins in Cheshire? ### What are some of the best cabins near Tanglewood Music Centre in Cheshire? ## Explore a world of travel with Expedia - 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