Title: Holiday Rentals The Berkshires from £95: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [The Berkshires Travel Guide](https://expedia.co.uk/The-Berkshires.dx6047665)[Hotels in The Berkshires](https://expedia.co.uk/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[Flights to The Berkshires](https://expedia.co.uk/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-The-Berkshires.d6047665.Car-Hire-Guide)[The Berkshires Holidays](https://expedia.co.uk/The-Berkshires.d6047665.Holidays-City-Breaks) ![The Berkshires featuring flowers](https://images.trvl-media.com/place/6047665/e95ad08c-cd3f-48ea-b01c-31171bbd50b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Photo courtesy of Berkshire Visitors Bureau # Search Holiday Rentals in The Berkshires - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 Tonight [17 Dec - 18 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-12-17&endDate=2025-12-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [18 Dec - 19 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-12-18&endDate=2025-12-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [19 Dec - 21 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [26 Dec - 28 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for The Berkshires holiday 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) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.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) ### Condo in Williamstown [](https://www.expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) 8.8/10 Excellent (2175) "Awesome for ski" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lazar £95 includes taxes & fees 14 Jan - 15 Jan 2026 [](https://www.expedia.co.uk/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/1000000/920000/911400/911313/9c53d20e.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo resort in Hancock [](https://www.expedia.co.uk/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) 8.2/10 Very good (987) "nice and clean, good customer service, but the room is smell. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Huang £150 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/250d56fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/69ce761a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/bae121bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/0ac89dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hancock [](https://www.expedia.co.uk/Hancock-Hotels-Must-See-Pirate-Suite-Ski-OnOff-Jiminy-Mtn-View-Fully-Redone-Decor.h98512708.Hotel-Information) 10/10 Exceptional (5) "It was great experience and we loved the ammenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carrie C. £184 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Hancock-Hotels-Must-See-Pirate-Suite-Ski-OnOff-Jiminy-Mtn-View-Fully-Redone-Decor.h98512708.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/70501210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/805904c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/32688657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/739b3363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hancock [](https://www.expedia.co.uk/Hancock-Hotels-Must-See-Cabin-Suite-Jiminy-Sleeps-4-Mountainview-Ski-OnOff-Country-Inn-Redone.h90182167.Hotel-Information) 10/10 Exceptional (8) "We had a wonderful 3 day weekend! Perfect location for families." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric B. £184 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Hancock-Hotels-Must-See-Cabin-Suite-Jiminy-Sleeps-4-Mountainview-Ski-OnOff-Country-Inn-Redone.h90182167.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/9c846f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/2a4ba750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/w1008h683x16y0-72a8567d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/a110f773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hancock [](https://www.expedia.co.uk/Hancock-Hotels-SKI-ONOFF-1BR-SUITE-1ST-FLR-SLEEPS-4-JIMINY-PEAK.h69787457.Hotel-Information) 10/10 Exceptional (23) "This property is spacious, clean and well- appointed. I would stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda M. £184 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Hancock-Hotels-SKI-ONOFF-1BR-SUITE-1ST-FLR-SLEEPS-4-JIMINY-PEAK.h69787457.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/b5482417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/9e312028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/w905h678x0y5-7353a588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/3663d99c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hancock [](https://www.expedia.co.uk/Hancock-Hotels-Disney-Magic-At-Jiminy-Must-See-Gorgeous-Sleeps-4.h78537603.Hotel-Information) 9.8/10 Exceptional (18) "We enjoyed our stay in this adorable Disney Themed condo. The attention to detail in the theming was fantastic and the condo was perfect for our February Vacation ski trip." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allison V. £184 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Hancock-Hotels-Disney-Magic-At-Jiminy-Must-See-Gorgeous-Sleeps-4.h78537603.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/dcb799f2.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) ### Holiday Home in Great Barrington [](https://www.expedia.co.uk/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. £202 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1080h783x0y5-9ee375ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h806x0y5-6945b1ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/a814c17c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/c54967a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Hancock [](https://www.expedia.co.uk/Hancock-Hotels-UNIQUE-Gnome-Themed-1BR-Condo.h74312811.Hotel-Information) 10/10 Exceptional (14) "Clean, comfortable place with nice amenities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike H. £290 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Hancock-Hotels-UNIQUE-Gnome-Themed-1BR-Condo.h74312811.Hotel-Information) ![TV, DVD player, books](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/b31564d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/a21be151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/w1333h900x16y0-bf275b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/56cd6111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hancock [](https://www.expedia.co.uk/Hancock-Hotels-Must-See-Jurassic-Dino-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h90786767.Hotel-Information) 10/10 Exceptional (3) "We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jen B. £184 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Hancock-Hotels-Must-See-Jurassic-Dino-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h90786767.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/949e9107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/97765f2f_edited_8669.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/63833f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/643b3865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hancock [](https://www.expedia.co.uk/Hancock-Hotels-Chic-2BR-Suite-On-Jiminy-Mtn-Sleeps-8-Gorgeous.h76713290.Hotel-Information) 9.6/10 Exceptional (30) "Great and clean property! Very easy to access and good parking too." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd A. £248 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Hancock-Hotels-Chic-2BR-Suite-On-Jiminy-Mtn-Sleeps-8-Gorgeous.h76713290.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/c3b6bbdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/b3464458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/9c369939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/83729050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Lanesborough [](https://www.expedia.co.uk/Lanesborough-Hotels-Cozy-Rustic-Apt-In-18th-C-Berkshire-Farmhouse.h73728934.Hotel-Information) 9.6/10 Exceptional (67) "We had a lovely stay! The studio was comfortable, clean, and just what we needed. Our hosts were friendly and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janice L. [](https://www.expedia.co.uk/Lanesborough-Hotels-Cozy-Rustic-Apt-In-18th-C-Berkshire-Farmhouse.h73728934.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/34492d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/82468102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/d1c43c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/7e1d3e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Hancock [](https://www.expedia.co.uk/Hancock-Hotels-2-BR-Condo-Mountain-Views-At-Jiminy-Peak-Sleeps-7.h111663271.Hotel-Information) 8.0/10 Very good (8) "Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) PK N. £257 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Hancock-Hotels-2-BR-Condo-Mountain-Views-At-Jiminy-Peak-Sleeps-7.h111663271.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/5dc2bebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/14ecae77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/12b81391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/f0c8191e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Florida [](https://www.expedia.co.uk/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.Hotel-Information) 10/10 Exceptional (4) "Place was super clean. Beds were comfortable. Location was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tristan e. £258 includes taxes & fees 23 Dec - 24 Dec [](https://www.expedia.co.uk/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.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) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/83d3f833_edited_d758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/162d61f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Sherwood Forest [](https://www.expedia.co.uk/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. £285 includes taxes & fees 22 Dec - 23 Dec [](https://www.expedia.co.uk/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/8a26cf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/11a36f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/976ef973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/184c6f2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Hancock [](https://www.expedia.co.uk/Hancock-Hotels-Spacious-3BR-3BA-Ski-OnOff-Jiminy-Mountain-Resort.h67635438.Hotel-Information) 9.8/10 Exceptional (72) "We had a wonderful stay, thank you! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary L. £410 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Hancock-Hotels-Spacious-3BR-3BA-Ski-OnOff-Jiminy-Mountain-Resort.h67635438.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/ec8e2057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/4fb8018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/0ab9f2e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/137726e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Hinsdale [](https://www.expedia.co.uk/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information) 9.8/10 Exceptional (34) "Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lindsey E. £368 includes taxes & fees 21 Dec - 22 Dec [](https://www.expedia.co.uk/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/af01e53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/347359ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/c04d3199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/dba15cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Sherwood Forest [](https://www.expedia.co.uk/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information) 9.6/10 Exceptional (10) "Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James D. £290 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information) ![1 bedroom, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/a0875211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/dabbf205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/4ee3217b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/edf0cab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Adams [](https://www.expedia.co.uk/Adams-Hotels-Penthouse-Apartment-On-Park-Street.h122136838.Hotel-Information) 9.6/10 Exceptional (13) "Adams is a beautiful town and looks and feels like the appalachian trail! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) judy r. £184 includes taxes & fees 17 Jan - 18 Jan 2026 [](https://www.expedia.co.uk/Adams-Hotels-Penthouse-Apartment-On-Park-Street.h122136838.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) ### Cabin in Sheffield [](https://www.expedia.co.uk/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information) 10/10 Exceptional (9) "Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) deborah d. £530 includes taxes & fees 21 Dec - 22 Dec [](https://www.expedia.co.uk/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/4ac9d6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Bungalow | Living area](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/bc7f49dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/fd380371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Camping in Williamstown [](https://www.expedia.co.uk/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) 10/10 Exceptional (7) "Perfect place for a relaxing getaway! We loved everything! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cammie £142 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Williamstown-Hotels-Huttopia-Berkshires.h113777287.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.co.uk/Hotel-Search?startDate=2025-12-31&endDate=2026-01-01®ionId=6047665&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=CABIN) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=APARTMENT) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=COTTAGE) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=CONDO) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=CHALET) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=VILLA) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FThe-Berkshires-Holiday-Rentals.d6047665.Travel-Guide-HolidayRentals)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FThe-Berkshires-Holiday-Rentals.d6047665.Travel-Guide-HolidayRentals) ## Top The Berkshires Hotel Reviews ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful . " [](https://expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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.co.uk/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.co.uk/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![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 "The room was fantastic, cozy as can be! Also, as soon as you walk into the lobby it looked wonderful! The Manager, Jennifer was so nice to talk too! She made sure everything with room, etc. was good! She was a delight!" [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.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.co.uk/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 "Clean room, friendly staff. " [](https://expedia.co.uk/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.co.uk/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.co.uk/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.co.uk/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ## Find out more about The Berkshires **Everything you need to know about** **The Berkshires** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the The Berkshires holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **The Berkshires holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of The Berkshires holiday rentals we have selected for you start as low as £95 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 holiday 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 holiday. 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 Holiday Rental Destinations - Trending destinations on Expedia.co.uk - All accommodation types in The Berkshires - [Stamford Holiday Rentals ](https://expedia.co.uk/Stamford-Holiday-Rentals.d6489.Travel-Guide-HolidayRentals) - [Dorset Holiday Rentals ](https://expedia.co.uk/Dorset-Holiday-Rentals.d184046.Travel-Guide-HolidayRentals) - [Lake George Holiday Rentals ](https://expedia.co.uk/Lake-George-Holiday-Rentals.d6055969.Travel-Guide-HolidayRentals) - [Providence Holiday Rentals ](https://expedia.co.uk/Providence-Holiday-Rentals.d180015.Travel-Guide-HolidayRentals) - [New York Holiday Rentals ](https://expedia.co.uk/New-York-Holiday-Rentals.d178293.Travel-Guide-HolidayRentals) - [Boston Holiday Rentals ](https://expedia.co.uk/Boston-Holiday-Rentals.d178239.Travel-Guide-HolidayRentals) - 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