Title: The Berkshires Vacation Rentals from CA $151: 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 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [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 two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in The Berkshires ## Our top choices for The Berkshires vacation rentals ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.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) ![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) ### Vacation Village in the Berkshires Williamstown 8.6/10 Excellent (2017) "All around loved everything about the place! " CA $127 CA $157 total includes taxes & fees Oct 7 - Oct 8 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/662f1ebe.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/1000000/920000/911400/911313/9c53d20e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jiminy Peak Mountain Resort Hancock 8.2/10 Very good (979) "Staff was very nice and helpful. Property was a little bit outdated but very clean and functional. Surroundings are beautiful!!" CA $206 CA $230 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) ![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/b421cb54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/9dd9ba23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Tent](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/24b6d0d6.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 $136 CA $151 total includes taxes & fees Sep 25 - Sep 26 [](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) ![Game room](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f251fc45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ponds at Foxhollow Lenox 8.6/10 Excellent (130) "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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/e43d10e1.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 $223 CA $656 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Hancock-Hotels-Comfortable-Berkshires-Retreat-On-Mtn-Resort.h109434975.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/aa330ef5.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) ![Exterior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/5d0aa061.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) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c8837e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/34fa691f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hancock Village Inn at Jiminy Peak Hancock 10/10 Exceptional (13) "Amazing Inn. Cozy and everything we needed. " CA $829 CA $1,537 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/e175fcb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amore Estate - beautiful room with many places to explore and relax in. Lenox 9.0/10 Wonderful (28) "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/20000000/19220000/19210700/19210630/4f0cf212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19220000/19210700/19210630/21d7f1c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19220000/19210700/19210630/178916ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19220000/19210700/19210630/22dc99a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating Sherwood Forest 9.6/10 Exceptional (223) "Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires." [](https://www.expedia.ca/Becket-Hotels-Quiet-Comfortable-Cabin-5-Min-Walk-To-Swimming-And-Boating.h19210630.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) ![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) ![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) ![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 $510 CA $953 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.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) ![Outdoor dining](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/e427035e.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) ![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) ### 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) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/a5ddb496.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) ![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) ### Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table Pittsfield 9.8/10 Exceptional (147) "Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! " [](https://www.expedia.ca/Pittsfield-Hotels-Beautiful-8-Bedroom.h33492239.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/113000000/112910000/112907100/112907040/a9aff9ef_edited_2bff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112910000/112907100/112907040/803617dd.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/a355d2d8_edited_d350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, jetted tub, hair dryer, towels](https://images.trvl-media.com/lodging/113000000/112910000/112907100/112907040/1e5dd261_edited_4f4d.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) "We had a wonderful four night stay at this home in Williamstown. Kathy, the owner, was great and easy to reach. The home was thoughtfully and thoroughly appointed, comfortably accommodating our extended family of ten. The grounds were beautifully maintained and the views of the Berkshires were breathtaking. We wouldn’t hesitate to stay again and we would highly recommend this lovely property. " [](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/35000000/34350000/34341700/34341645/40ba9321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34341700/34341645/889170d3.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) ![Golf](https://images.trvl-media.com/lodging/35000000/34350000/34341700/34341645/w640h476x0y4-5c1b61d6.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) ![Interior](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/f0e2a743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/5809b528.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/c604c489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/232fb1b8.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) ![Interior](https://images.trvl-media.com/lodging/35000000/34010000/34008000/34007913/a4d043dc.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) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/35000000/34010000/34008000/34007913/2cd290f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Enjoy comfortable elegance in this secluded grand home located in town Lenox 10/10 Exceptional (73) "Great location for access to both Tanglewood and Lenox center. " [](https://www.expedia.ca/Lenox-Hotels-Enjoy-Comfortable-Elegance-In-This-Secluded-Grand-Home-Located-In-Town.h34007913.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/411deb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/f9227a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/ab438b32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/21218e1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-bedroom house in beautiful Berkshires, close to amenities! Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/5d30ef99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/f1ce2b15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/b7f5b609.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/2d1b7442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Florida Mountain Log Cabin! Florida 10/10 Exceptional (4) "Place was super clean. Beds were comfortable. Location was great." CA $294 CA $587 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.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) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39960000/39954400/39954364/e601a37c.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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/fbda7092.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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/9a679a9c.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=2025-10-08&endDate=2025-10-09®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 ![Hotel Downstreet, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Totally perfect for mass mocha" [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "everything-loved it!" [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.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 "Probably the nicest Holiday Inn Express we've stayed at. Clean, well-appointed rooms. Everything looks updated. And did I say clean?Really excellent coffee and generous hot breakfast. Friendly and helpful desk staff. " [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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 "Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//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 "We stayed for 5 nights and really enjoyed the surroundings and the drive to the property. The area is peaceful and quiet, with plenty to do for kids, including a mountain hike that even our 2- and 6-year-olds managed well. The grounds are beautiful for photos, very well maintained, and we often saw the crew cleaning and painting the sidewalks. I booked 2 suites, which were a good size for a family of four and offered plenty of space. The only downsides were that check-in felt a bit tedious it took several tries to swipe my card and there was no housekeeping service or follow-up to check on amenities during our stay. A self check-in option would make things smoother. Overall, we loved the quietness, the family-friendly activities, and the clean, well-kept property. With a few improvements in guest service, this could easily be a 5-star experience." [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Jiminy Peak Mountain Resort](//images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830_y.jpg) ### Jiminy Peak Mountain Resort 10/10 Excellent "Absolutely beautiful " [](https://expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Excellent location. Friendly staff. " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![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 "Perfect for an overnight for the Tanglewood concert" [](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 "A great place if you appreciate and like history. The lobby is filled with antiques and the porch is great to rock in a chair and sip some wine. Parking is no issue and you can walk to local restaurants and shops. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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 $151 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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[Things to do in Cape Cod](https://expedia.ca/Things-To-Do-In-Cape-Cod.d180061.Travel-Guide-Activities) - [Things to do in Salem](https://expedia.ca/Things-To-Do-In-Salem.d6600.Travel-Guide-Activities) Packages - [Salem Vacations](https://expedia.ca/Salem.d6600.Destination-Travel-Guides) - [Cape Cod Vacations](https://expedia.ca/Cape-Cod.d180061.Destination-Travel-Guides) - [Martha's Vineyard Vacations](https://expedia.ca/Marthas-Vineyard.d6047691.Destination-Travel-Guides) Vacation Rentals - [Cape Cod Vacation Rentals](https://expedia.ca/Cape-Cod-Vacation-Rentals.d180061.Travel-Guide-VacationRentals) General - [Visit Downtown Boston](https://expedia.ca/Boston-Downtown-Boston.dx6340396) - [Visit Charlestown](https://expedia.ca/Boston-Charlestown.dx88542) - [Visit Seaport District](https://expedia.ca/Boston-Seaport-District.dx6146535) - [Visit Cape Cod](https://expedia.ca/Cape-Cod.dx180061) - [Visit Martha's Vineyard](https://expedia.ca/Marthas-Vineyard.dx6047691) - [Visit Hyannis Port](https://expedia.ca/Hyannis-Port.dx183332) - 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