Title: Berkshire County Vacation Home Rentals from CA $417: 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) ![The Berkshires featuring snow as well as a family](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/71000/71827-The-Berkshires.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 Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [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) ## Featured Vacation Homes in Berkshire County ![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/406cc767.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) ![Exterior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/c57b8d60.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) ### Pet Friendly Riverfront Home in Great Barrington Great Barrington 8.8/10 Excellent (3) "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 $284 CA $417 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51270000/51267800/51267781/7815c72a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51270000/51267800/51267781/8f540e43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/52000000/51270000/51267800/51267781/ef48a18d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/52000000/51270000/51267800/51267781/15d1bd07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE Great Barrington 10/10 Exceptional (40) "Our stay exceeded our expectations.The home is beautiful, cozy, very well maintained, appointed and located. We felt relaxed from the moment we walked in the door. We will definitely be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Courtney S. [](https://www.expedia.ca/Great-Barrington-Hotels-NEWLY-REMODELED-3-BEDROOM-COUNTRY-CASTLE.h51267781.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) ![Interior](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/7d7a19ab.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) ### Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country Stockbridge 10/10 Exceptional (132) "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) ![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) ![Living area](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/b2d17216.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) ![Interior](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/960bf7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amore Estate - beautiful room with many places to explore and relax in. Lenox 9.2/10 Wonderful (32) "Beautiful property with tons of space and fantastic for a group of friends or family" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg S. [](https://www.expedia.ca/Lenox-Hotels-October-Mountain-Escape.h91593496.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) ![Interior](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/2267bfa7.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) ![Smart TV, fireplace, foosball](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/8b9796c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge! Lee 9.6/10 Exceptional (16) "My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Annie C. [](https://www.expedia.ca/Lee-Hotels-Cordelia-By-AvantStay-Amazing-Backyard.h101271254.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39960000/39954400/39954364/c74b811e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/40000000/39960000/39954400/39954364/392c12f5.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/40000000/39960000/39954400/39954364/c7aa0091.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39960000/39954400/39954364/c3f7f916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB! Great Barrington 10/10 Exceptional (55) "We were taking our first family ski trip and were lucky to stay at this great house which is only 10 minutes from Butternut. Super convenient, very comfortable and the huge kitchen was a perfect place for our family to gather after a day on the slopes. We loved it and would happily return next year!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin R. [](https://www.expedia.ca/Great-Barrington-Hotels-Premiere-Berkshire-Country-Estate-W-Private-Pool-Tennis-Court-5-Mins-To-GB.h39954364.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119780000/119777200/119777182/832bba64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119780000/119777200/119777182/29d47a86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119780000/119777200/119777182/52af850a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119780000/119777200/119777182/a13ca413.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quiet 2BR/1BA Forest-View Barn Apartment – Newly Renovated, Peaceful Escape West Stockbridge 7.4/10 Good (3) "Beautiful quiet escape. Host was very prompt with answers to questions I had. Very nice re-model. I will definitely be back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher W. [](https://www.expedia.ca/West-Stockbridge-Hotels-Quiet-2BR1BA-Forest-View-Barn-Apartment-Newly-Renovated.h119777182.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101580000/101578300/101578238/95374065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101580000/101578300/101578238/42453f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101580000/101578300/101578238/9dd63711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101580000/101578300/101578238/1bd07673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stay Lakeside This Summer! Great Barrington 9.8/10 Exceptional (79) "Beautiful lake views, comfy and cozy house! We had a wonderful time. Thank you for sharing your home with us. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne-Marie A. [](https://www.expedia.ca/Great-Barrington-Hotels-Lakeside-Retreat-In-Great-Barrington.h101578238.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/58b0972d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/636f9a34.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/fb68a83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5-bedroom house in charming Lee with WiFi Lee 8.0/10 Very good (1) "House was large, clean, and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John Z. CA $595 CA $1,108 total includes taxes & fees Dec 4 - Dec 5 [](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/31000000/30780000/30777100/30777071/afd0b229.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) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/0f6c9404.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) ### Peace and quiet on the lake Sherwood Forest 9.6/10 Exceptional (227) "Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anika J. [](https://www.expedia.ca/Becket-Hotels-Peace-And-Quiet-On-The-Lake.h30777071.Hotel-Information) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/113000000/112910000/112907100/112907040/59936f37_edited_32df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112910000/112907100/112907040/c77460d1_edited_b3c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112910000/112907100/112907040/bd5917a8_edited_d7e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112910000/112907100/112907040/94cc6453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Contemporary Berkshire Home with Views of Taconic Golf Course Williamstown 10/10 Exceptional (11) "Lovely property. Well kept house, nicely decorated. Very much enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARK S. [](https://www.expedia.ca/Williamstown-Hotels-Contemporary-Berkshire-Home-With-Views-Of-Taconic-Golf-Course.h112907040.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78440000/78432200/78432175/56ecd142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78440000/78432200/78432175/267faaac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78440000/78432200/78432175/1cc2075b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78440000/78432200/78432175/ee760f47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee. Lee 10/10 Exceptional (25) "We had another great weekend stay with friends! Can’t say enough good things about the house and property and location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robin M. [](https://www.expedia.ca/Lee-Hotels-Lakeview-Retreat-Mins-To-Downtown-Lenox.h78432175.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) ![Exterior](https://images.trvl-media.com/lodging/70000000/69770000/69763300/69763258/128e06d4.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) ### Hearts Desire is a furnished whole house in a small, colorful garden center. Lanesborough 10/10 Exceptional (97) "This was our third time at this property. We still love it and look forward to returning again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa P. [](https://www.expedia.ca/Lanesborough-Hotels-Hearts-Desire-Is-A-Furnished-Whole-House-In-A-Small.h69763258.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/119000000/118950000/118948800/118948741/255e6372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118950000/118948800/118948741/8d79ff6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118950000/118948800/118948741/62abcc3d.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/119000000/118950000/118948800/118948741/b4775802.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded 4 bedroom home with sweeping mountain views in Williamstown Williamstown 9.6/10 Exceptional (5) [](https://www.expedia.ca/Williamstown-Hotels-Secluded-4-Bedroom-Home-With-Sweeping-Mountain-Views-In-Williamstown.h118948741.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) ![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/95ce4320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/461d5056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### General Williams Estate House Lenox/Stockbridge Stockbridge 9.8/10 Exceptional (110) "This was a great place to house our family of 12 during the weekend of our daughter’s wedding. There was plenty of space for everyone to gather. The beds were comfortable and all the bedrooms upstairs had their own bathroom - so nice! The house made our weekend extra special. Definitely recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fern L. [](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) ![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) ![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) ### Woodland 5-BR Retreat 5-Min to Jiminy Peak Hancock 10/10 Exceptional (12) "The house was beautiful, very clean and well kept." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica G. [](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/46000000/45680000/45675900/45675829/10f0cfa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/46000000/45680000/45675900/45675829/d3f7ae31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/46000000/45680000/45675900/45675829/ddf6e6e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/46000000/45680000/45675900/45675829/59176dc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Victorian Walk to Main Street Great Barrington 10/10 Exceptional (25) "The house was perfect for our long weekend in Great Barrington. It’s very comfortable, clean, and well taken care of. The location is perfect. We loved being able to walk right into town. Highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine L. [](https://www.expedia.ca/Great-Barrington-Hotels-Modern-Victorian-Walk-To-Main-Street.h45675829.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) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69560000/69551900/69551862/a85107c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sophisticated Lenox Retreat by Evergreen Home Lenox 9.8/10 Exceptional (9) "Well laid out, and great set-up for our family stay in Lenox for a wedding. All the amenities we needed, and back deck was comfortable for some down time. Highly recommended." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul B. [](https://www.expedia.ca/Lenox-Hotels-Sophisticated-Lenox-Retreat-By-Evergreen-Home.h69551862.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69650000/69640700/69640625/93610870.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) ### Country Living just minutes from Everything! Pittsfield 10/10 Exceptional (29) "Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle D. [](https://www.expedia.ca/Pittsfield-Hotels-Come-Experience-The-Berkshires.h69640625.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18761000/18760908/270-12286aa8.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) ### Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++ Lenox 9.4/10 Exceptional (62) "We had a wonderful stay. The house was well appointed and comfortable for hanging out." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mallory V. [](https://www.expedia.ca/Lenox-Hotels-Luxury-Fox-Hollow-Estate-Home-On-Laurel-Lake-Dream-Location.h18760908.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=2025-11-18&endDate=2025-11-19®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 ![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Everything was fine just no shampoo in the dispencer" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean, convenience, great staff, quiet, beautiful and secluded yet close to everything! Thank you" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Vacation Village in the Berkshires](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "The amenities are great. The pool and hot tub are very comfortable temperatures, pool tables, ping pong, foosball, arcade games, movie theater, and more." [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Staff was friendly, nice area, near things but set back so you didn’t hear the traffic." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Williams Inn](//images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Didn’t have the breakfast. Only drawback was the beds. Mattresses made our backs hurt." [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Monument Mountain Motel](//images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94_y.jpg) ### Monument Mountain Motel 10/10 Excellent "Yes" [](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Lovely hotel in the middle of a non very busy town. " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "The restaurant was so delicious …the fries were the best fries I have ever had …will never forget how tasty they were !!!" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "The Red Lion Hotel was a great place to stay!! I would definitley come back again and stay there! I loved the bar downstairs and the restaurant! Our room was perfect and we had lots of room! The bed was super comfy - a marshmallow bed!! LOL! The location was nice to walk to the different shops in town! Fun place! " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ## Find out more about Berkshire County ## Berkshire County Vacation Homes information | Number of reviews | 821 | | --- | --- | | Accommodation | 337 Vacation Homes | | Lowest Price | CA $417 | | Highest Price | CA $1,108 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Aparthotels in Dalton](https://www.expedia.ca/Dalton-Apart-Hotels.d6911-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Dalton](https://www.expedia.ca/Dalton-Bed-And-Breakfast.d6911-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Dalton](https://www.expedia.ca/Dalton-Hotels-Cheap-Hotels.0-0-d6911-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Dalton](https://www.expedia.ca/Dalton-Hotels-Family-Hotel.0-0-d6911-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Dalton](https://www.expedia.ca/Dalton-Hotels-Spa-Hotel.0-0-d6911-tSpaHotel.Travel-Guide-Filter-Hotels) - 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