Title: The Berkshires Vacation Rentals from CA $118: Short-Term Rentals for 2025 | Expedia.ca [The Berkshires Travel Guide](https://expedia.ca/The-Berkshires.dx6047665)[Hotels in The Berkshires](https://expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[Flights to The Berkshires](https://expedia.ca/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Car Rentals](https://expedia.ca/Car-Rentals-In-The-Berkshires.d6047665.Car-Rental-Guide)[The Berkshires Vacation Packages](https://expedia.ca/The-Berkshires.d6047665.Destination-Travel-Guides) ![The Berkshires showing snow and snowboarding](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/71000/71823-The-Berkshires.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # The Berkshires 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 In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in The Berkshires ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/18127ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/16150550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires Williamstown 8.6/10 Excellent (2039) "Really nice place at a reasonable price" CA $92 CA $118 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 Bedroom Condo 1/2 mile from base | In-room dining](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/40940c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/662f1ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jiminy Peak Mountain Resort Hancock 8.2/10 Very good (981) "Staff was very nice and helpful. Property was a little bit outdated but very clean and functional. Surroundings are beautiful!!" CA $193 CA $216 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/137f5231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/3f004a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/2b2e1d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Tent](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/b96863a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Huttopia Berkshires Williamstown 10/10 Exceptional (4) "Perfect place for a relaxing getaway! We loved everything! " CA $137 CA $153 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) ![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f5477a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/ebd04e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ponds at Foxhollow Lenox 8.6/10 Excellent (131) "We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights" [](https://www.expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/5bf808fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/92ba9b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/aa306e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/d7946d7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Kemble- Built by a US Secretary of State in Lenox Lenox 10/10 Exceptional (17) "Loved the property. Perfect for our gathering." [](https://www.expedia.ca/Lenox-Hotels-The-Kemble-Built-By-A-US-Secretary-Of-State-In-Lenox.h76003386.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) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/e175fcb2.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 9.0/10 Wonderful (30) "Beautiful, spacious house in a great location!" [](https://www.expedia.ca/Lenox-Hotels-October-Mountain-Escape.h91593496.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/5d0aa061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c8837e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/ed3ffaa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c189cee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hancock Village Inn at Jiminy Peak Hancock 10/10 Exceptional (14) "Amazing Inn. Cozy and everything we needed. " CA $836 CA $1,550 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/18066543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/e43d10e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/dcf5df54_edited_d00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/f076ba69_edited_5004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable Berkshires retreat on mtn resort, SISO Hancock 8.8/10 Excellent (6) "Kind and responsive host." CA $225 CA $662 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Hancock-Hotels-Comfortable-Berkshires-Retreat-On-Mtn-Resort.h109434975.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) ![Exterior](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/bc016b9b.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) ### Peace and quiet on the lake Sherwood Forest 9.6/10 Exceptional (222) "Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. " [](https://www.expedia.ca/Becket-Hotels-Peace-And-Quiet-On-The-Lake.h30777071.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/9fa6f837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/565807cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/13f82703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/edf60411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Guesthouse Cabin vacation rentals in Berkshire County Sheffield 10/10 Exceptional (9) "Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. " CA $515 CA $969 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.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) ![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) ![3 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/113000000/112910000/112907100/112907040/e281c397.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Contemporary Berkshire Home with Views of Taconic Golf Course Williamstown 10/10 Exceptional (8) "Lovely property. Well kept house, nicely decorated. Very much enjoyed our stay." [](https://www.expedia.ca/Williamstown-Hotels-Contemporary-Berkshire-Home-With-Views-Of-Taconic-Golf-Course.h112907040.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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/85b23873.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 (149) "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) ![Interior](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/4b89dca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, free WiFi](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/eb0a776d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/w1024h683x0y1-30c5b99d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/61b3f659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Island - Largest Fresh Water Reservoir in Mass Otis 8.8/10 Excellent (8) "We had a great time. The owner Bill was a great host." [](https://www.expedia.ca/Otis-Hotels-Private-Island-On-Largest-Fresh-Water-Reservoir-In-Mass-Ski-Boat-Included.h67255071.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107880000/107876100/107876022/20a59d87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/108000000/107880000/107876100/107876022/679a9bd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107880000/107876100/107876022/221764d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107880000/107876100/107876022/25996a66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton Dalton 10/10 Exceptional (12) "We came out to see James Taylor on the 4th. Kathy and Kit were terrific hosts. Friendly, accommodating and their home was very comfortable and clean. We would definitely rent from them again. Thank you! " [](https://www.expedia.ca/Dalton-Hotels-Bright.h107876022.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34341700/34341645/40ba9321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/35000000/34350000/34341700/34341645/w640h476x0y4-5c1b61d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/35000000/34350000/34341700/34341645/2e6a29c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/35000000/34350000/34341700/34341645/820f3267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox Hancock 9.8/10 Exceptional (69) "Beautiful location, very spacious, comfortable and clean." [](https://www.expedia.ca/Williamstown-Hotels-Huge-Beautiful-House-Fits-2-Families-16-Acres-Low-Rates-2-Min-From-Jiminy-Peak.h34341645.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) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/4ebdefe3.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) ![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) ![Interior](https://images.trvl-media.com/lodging/35000000/34010000/34008000/34007913/a4d043dc.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) ![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/772f14ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/f98a9691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, printers](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/6ef7616b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/ee5ac04d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room Great Barrington 10/10 Exceptional (1) "Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!" CA $878 CA $1,965 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.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) ![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) ![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) ### Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB! Great Barrington 10/10 Exceptional (55) "We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!" [](https://www.expedia.ca/Great-Barrington-Hotels-Premiere-Berkshire-Country-Estate-W-Private-Pool-Tennis-Court-5-Mins-To-GB.h39954364.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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/9a679a9c.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) ### 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) 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=2025-10-20&endDate=2025-10-21®ionId=6047665&adults=2&sort=RECOMMENDED&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%2FThe-Berkshires-Vacation-Rentals.d6047665.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FThe-Berkshires-Vacation-Rentals.d6047665.Travel-Guide-VacationRentals) ## Top The Berkshires 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 "Clean place. Good breakfast and friendly staff" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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 "Great place! Food excellent ss well!" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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 "I honestly just spent the night as part of a longer road-trip, but I found it quiet and comfortable, and the room was very clean when I arrived. Slept well, but unfortunately had to leave before breakfast." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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 "Great!" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/4c557ede_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Comfortable, quiet and in a great location" [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "There was construction noise next door." [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Clean Room, good parking, conveniently located near down town." [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![The Williams Inn](//images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Lovely place with lovely people. Food is great. " [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Absolutely loved this place. It was quant, hip, affordable and just all around stunning! Worth it all! Would stay there again in a heartbeat. " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ## Find out more about The Berkshires **Everything you need to know about** **The Berkshires** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the The Berkshires vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect The Berkshires vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **The Berkshires vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in The Berkshires. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A The Berkshires vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of The Berkshires vacation rentals we have selected for you start as low as CA $118 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on The Berkshires rentals** At Expedia, we put the best The Berkshires vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top The Berkshires rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream The Berkshires vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around The Berkshires. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Recommended Vacation Rental Destinations - Trending destinations on Expedia.ca - All accommodation types in The Berkshires - [Stamford Vacation Rentals](https://expedia.ca/Stamford-Vacation-Rentals.d6489.Travel-Guide-VacationRentals) - [Lake George Vacation Rentals](https://expedia.ca/Lake-George-Vacation-Rentals.d6055969.Travel-Guide-VacationRentals) - [Providence Vacation Rentals](https://expedia.ca/Providence-Vacation-Rentals.d180015.Travel-Guide-VacationRentals) - [New York Vacation Rentals](https://expedia.ca/New-York-Vacation-Rentals.d178293.Travel-Guide-VacationRentals) - [Boston Vacation Rentals](https://expedia.ca/Boston-Vacation-Rentals.d178239.Travel-Guide-VacationRentals) - [Brighton Vacation Rentals](https://expedia.ca/Brighton-Vacation-Rentals.d10657.Travel-Guide-VacationRentals) - 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[Osoyoos Vacation Rentals](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals) - [Mont Tremblant Vacation Rentals](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals) - [Big White Ski Resort Vacation Rentals](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals) - [Ontario Vacation Rentals](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations) - [British Columbia Vacation Rentals](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations) - [Prince Edward Island Vacation Rentals](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations) - [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals) - [Vacation Homes in The Berkshires](https://expedia.ca/The-Berkshires-Private-Vacation-Homes.d6047665-aaPrivateVacationHomes.Travel-Guide-Accommodation) - 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[Visit Nantucket Island](https://expedia.ca/Nantucket-Island.dx6047676) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)