Title: Berkshire County Vacation Home Rentals from CA $363: Search Top Private Vacation Homes for Rent | Expedia.ca [Berkshire County Hotels](https://expedia.ca/Destinations-In-Berkshire-County.d553248635083901436.Hotel-Destinations)[Vacation Rentals in Berkshire County](https://expedia.ca/Destinations-In-Berkshire-County.d553248635083901436.Vacation-Rental-Destinations)[Berkshire County Car Rentals](https://expedia.ca/Destinations-In-Berkshire-County.d553248635083901436.Car-Rental-Destinations)[Berkshire County Vacations](https://expedia.ca/Berkshire-County.d553248635083901436.Destination-Travel-Guides) ![Williamstown which includes café scenes](https://images.trvl-media.com/place/7859/20112747-2c45-42f7-89fe-e3ed195e2395.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Berkshire County Vacation Rentals ## Compare and save - ![](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 [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&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) ## Top Cities in Berkshire County ![Williamstown which includes café scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105596-Williamstown.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Williamstown [](https://expedia.ca/Williamstown-Private-Vacation-Homes.d7859-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![North Adams featuring autumn colours](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105306-The-Berkshires.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### North Adams [](https://expedia.ca/North-Adams-Private-Vacation-Homes.d9137-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Lenox featuring an administrative building](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105615-Lenox.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Lenox [](https://expedia.ca/Lenox-Private-Vacation-Homes.d8587-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Great Barrington](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/238000/238015-Great-Barrington.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Great Barrington [](https://expedia.ca/Great-Barrington-Private-Vacation-Homes.d110336-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/1/5c9675f1022a9d16db477be7ba7a1dae.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Stockbridge [](https://expedia.ca/Stockbridge-Private-Vacation-Homes.d162575-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Pittsfield showing a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105316-The-Berkshires.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Pittsfield [](https://expedia.ca/Pittsfield-Private-Vacation-Homes.d9478-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Our top choices for Berkshire County vacation homes ![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/406cc767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/121000000/120310000/120304900/120304823/59edf6fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, eco-friendly cleaning products](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/780d89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Great Barrington [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) 9.4/10 Exceptional (6) CA $279 CA $409 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.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) ![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) ![Interior](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/7d7a19ab.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) ### Vacation Home in Stockbridge [](https://www.expedia.ca/West-Stockbridge-Hotels-Location-Location-Berkshire-Glamour.h33932760.Hotel-Information) 10/10 Exceptional (135) "Clean house, well appointed, great location, responsive owner" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sara m. [](https://www.expedia.ca/West-Stockbridge-Hotels-Location-Location-Berkshire-Glamour.h33932760.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95210000/95207600/95207502/fb316035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95210000/95207600/95207502/e884a87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/96000000/95210000/95207600/95207502/1359a0ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95210000/95207600/95207502/0a528814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lanesborough [](https://www.expedia.ca/Lanesborough-Hotels-Cozy-Lake-House-With-Hot-Tub-Enjoy-Everything-The-Berkshires-Have-To-Offer.h95207502.Hotel-Information) 10/10 Exceptional (8) "Everything was just as advertised and we really enjoyed the view and the hot tub. Perfect spot for a quick getaway! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy B. [](https://www.expedia.ca/Lanesborough-Hotels-Cozy-Lake-House-With-Hot-Tub-Enjoy-Everything-The-Berkshires-Have-To-Offer.h95207502.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/afd0b229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/f26456ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/2598e461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/bc016b9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Sherwood Forest [](https://www.expedia.ca/Becket-Hotels-Peace-And-Quiet-On-The-Lake.h30777071.Hotel-Information) 9.6/10 Exceptional (230) "Great communication, comfortable home, love the location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan C. [](https://www.expedia.ca/Becket-Hotels-Peace-And-Quiet-On-The-Lake.h30777071.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/a5ddb496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/7e362400.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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/85b23873.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Beautiful-8-Bedroom.h33492239.Hotel-Information) 9.8/10 Exceptional (150) "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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah A. [](https://www.expedia.ca/Pittsfield-Hotels-Beautiful-8-Bedroom.h33492239.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) ![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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/65000000/64150000/64145900/64145854/0133e83c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lanesborough [](https://www.expedia.ca/Lanesborough-Hotels-Wildlife-Cottage-By-The-Lake.h64145854.Hotel-Information) 9.6/10 Exceptional (74) "This house is immaculate. Loved the fire pit and the jacuzzi. Very comfortable house. We spent quite a bit of time relaxing on the deck of the living room. We did get a bit lost getting there, but the caretaker, Jill, was readily available and not only helped us with directions, but gave us suggestions on where to go for groceries, etc. Very friendly and helpful woman. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara A. [](https://www.expedia.ca/Lanesborough-Hotels-Wildlife-Cottage-By-The-Lake.h64145854.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/f8fd77b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/36d358fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/2267bfa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/b18d7fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lee [](https://www.expedia.ca/Lee-Hotels-Cordelia-By-AvantStay-Amazing-Backyard.h101271254.Hotel-Information) 9.6/10 Exceptional (19) "Great communication, perfect location for everything we wanted to do that weekend and a beautiful home! We used the indoor and outdoor spaces and had a wonderful time!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie L. [](https://www.expedia.ca/Lee-Hotels-Cordelia-By-AvantStay-Amazing-Backyard.h101271254.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102040000/102036900/102036815/9492003f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102040000/102036900/102036815/2e9fc1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102040000/102036900/102036815/05c29f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102040000/102036900/102036815/w981h960x0y0-dffb4572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lee [](https://www.expedia.ca/Lee-Hotels-Lee-Manor-For-Lasting-Memories.h102036815.Hotel-Information) 10/10 Exceptional (21) "Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jennifer r. [](https://www.expedia.ca/Lee-Hotels-Lee-Manor-For-Lasting-Memories.h102036815.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) ![Living area](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/b2d17216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lenox [](https://www.expedia.ca/Lenox-Hotels-October-Mountain-Escape.h91593496.Hotel-Information) 9.2/10 Wonderful (33) "Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacquie S. [](https://www.expedia.ca/Lenox-Hotels-October-Mountain-Escape.h91593496.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/ecdea449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/4bbc4f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/162d61f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Sherwood Forest [](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information) 10/10 Exceptional (5) "We loved it! Lots of local hiking trails and a wonderful relaxing place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon K. CA $201 CA $515 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/fbda7092.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) ### Vacation Home in Stockbridge [](https://www.expedia.ca/Stockbridge-Hotels-A-Grand-Estate-In-Historic-Stockbridge.h33960335.Hotel-Information) 10/10 Exceptional (104) "Great house with gracious and responsive hosts. Everything in working order and the houseclean and grand." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David H. [](https://www.expedia.ca/Stockbridge-Hotels-A-Grand-Estate-In-Historic-Stockbridge.h33960335.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) ![Interior](https://images.trvl-media.com/lodging/78000000/77190000/77189600/77189557/cb79f2ea.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) ![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) ### Vacation Home in Otis [](https://www.expedia.ca/Otis-Hotels-The-Meadows-House-Otis-Ridge-W-7-Person-Hot-Tub.h77189557.Hotel-Information) 9.6/10 Exceptional (39) "Beautiful property and location. Excellent communication from the host. Recommend and would visit again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory G. [](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/115000000/114160000/114155600/114155589/f64acfa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114160000/114155600/114155589/a6f06d58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, computer monitors](https://images.trvl-media.com/lodging/115000000/114160000/114155600/114155589/e6c9b6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, computer monitors](https://images.trvl-media.com/lodging/115000000/114160000/114155600/114155589/835ef8e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Williamstown [](https://www.expedia.ca/Williamstown-Hotels-Charming-Berkshires-Retreat-Minutes-To-Williamstown.h114155589.Hotel-Information) 9.2/10 Wonderful (9) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael w. [](https://www.expedia.ca/Williamstown-Hotels-Charming-Berkshires-Retreat-Minutes-To-Williamstown.h114155589.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) ![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) ![Pool](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/afeca776.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) ### Vacation Home in Stockbridge [](https://www.expedia.ca/General-Williams-Estate-House-LenoxStockbridge.h33509020.Hotel-Information) 9.8/10 Exceptional (111) "The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanna T. [](https://www.expedia.ca/General-Williams-Estate-House-LenoxStockbridge.h33509020.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102410000/102401300/102401286/bd3a7441.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102410000/102401300/102401286/7f1582c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102410000/102401300/102401286/a12e7bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/103000000/102410000/102401300/102401286/5d692b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Hancock [](https://www.expedia.ca/Pittsfield-Hotels-Woodland-5-BR-Retreat-5-Min-To-Jiminy-Peak.h102401286.Hotel-Information) 10/10 Exceptional (13) "Kids thought the best part of their vacation was being at this house! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laurel J. [](https://www.expedia.ca/Pittsfield-Hotels-Woodland-5-BR-Retreat-5-Min-To-Jiminy-Peak.h102401286.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69650000/69640700/69640625/4567d4f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69650000/69640700/69640625/90c10b4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69650000/69640700/69640625/93610870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69650000/69640700/69640625/95f1b2ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Come-Experience-The-Berkshires.h69640625.Hotel-Information) 10/10 Exceptional (29) "Very nice, very clean property. Everything you need. Communication with owner is excellent. My family and I were extremely comfortable here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Pittsfield-Hotels-Come-Experience-The-Berkshires.h69640625.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/c50e9e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/e0f691bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Great Barrington [](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) 9.8/10 Exceptional (26) "Enjoyed our stay!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fred W. CA $215 CA $363 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/121000000/120630000/120627000/120626960/f3ef79db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120630000/120627000/120626960/a71faaaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120630000/120627000/120626960/cde57065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120630000/120627000/120626960/bb61173c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Hancock [](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Slopeside-Getaway-Ski-Adventure.h120626960.Hotel-Information) [](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Slopeside-Getaway-Ski-Adventure.h120626960.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83230000/83225400/83225357/39f48ac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83230000/83225400/83225357/4f43cfd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83230000/83225400/83225357/50799d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83230000/83225400/83225357/be06a090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Stockbridge [](https://www.expedia.ca/Stockbridge-Hotels-Spacious-Modern-Berkshires-Getaway.h83225357.Hotel-Information) 10/10 Exceptional (8) "Beautiful house in a perfect location for what we were looking for! Zach was helpful when we needed something and we would love to come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony L. [](https://www.expedia.ca/Stockbridge-Hotels-Spacious-Modern-Berkshires-Getaway.h83225357.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69560000/69551900/69551862/64da04d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/70000000/69560000/69551900/69551862/b21de6d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69560000/69551900/69551862/ff6cc55d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69560000/69551900/69551862/73fbabc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lenox [](https://www.expedia.ca/Lenox-Hotels-Sophisticated-Lenox-Retreat-By-Evergreen-Home.h69551862.Hotel-Information) 9.8/10 Exceptional (9) "Very quaint location, clean property, and great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adrian R. [](https://www.expedia.ca/Lenox-Hotels-Sophisticated-Lenox-Retreat-By-Evergreen-Home.h69551862.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=2025-12-31&endDate=2026-01-01®ionId=553248635083901436&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%2FBerkshire-County-Private-Vacation-Homes.d553248635083901436-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FBerkshire-County-Private-Vacation-Homes.d553248635083901436-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Berkshire County Hotel Reviews ![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 "This is a wonderful place to stay. The breakfast is delicious. The pool and hot tub are delightful. The staff are like family. " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Awesome for ski" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![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 "Very clean. Nice amenities. Had everything you needed. " [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "We had a very nice experience staying at the Red Lion Inn. Our room was upgraded when checking in which was a nice surprise. The hotel was beautifully decorated for the season. We loved the cozy feel of the fireplace in the lobby especially on such a cold day. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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 "Hot tub was relaxing. Parking was easy. Restaurant within walking distance. If you forget anything dollar general close." [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "The rooms were very clean and well kept. The beds were very comfortable. The breakfast: There was no cereal or variety of breads like bagels. Yogurts were great. I do give them the benefit of the doubt on this because it was an off week, in between holidays. It was very quiet. Staff was wonderful. We will definitely be back. " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Lovely little elegant hotel. Beautiful well appointed rooms. Comfortable bed. Reasonably price. Great find. " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Nice room" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Great hospitality " [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ## Find out more about Berkshire County ## Berkshire County Vacation Homes information | Number of reviews | 950 | | ----------------- | ------------------ | | Accommodation | 332 Vacation Homes | | Lowest Price | CA $363 | | Highest Price | CA $515 | ## Explore a world of travel with Expedia - 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