Title: West Stockbridge Holiday Homes from £119: Search Holiday Homes in West Stockbridge | Expedia.co.uk [West Stockbridge Travel Guide](https://expedia.co.uk/West-Stockbridge.dx173346)[Hotels in West Stockbridge](https://expedia.co.uk/West-Stockbridge-Hotels.d173346.Travel-Guide-Hotels)[Holiday Rentals in West Stockbridge](https://expedia.co.uk/West-Stockbridge-Holiday-Rentals.d173346.Travel-Guide-HolidayRentals)[West Stockbridge Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-West-Stockbridge.d173346.Car-Hire-Guide)[West Stockbridge Holidays](https://expedia.co.uk/West-Stockbridge.d173346.Holidays-City-Breaks) ![Olivias Overlook - West Stockbridge, Massachusetts](https://images.trvl-media.com/place/173346/8a572978-a908-43ba-b1f1-0a856c5003da.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/173346/8a572978-a908-43ba-b1f1-0a856c5003da.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 In two weeks [17 Apr - 19 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=173346&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=173346&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [26 Jun - 28 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=173346&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [24 Jul - 26 Jul](https://www.expedia.co.uk/Hotel-Search?regionId=173346&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for West Stockbridge holiday homes ![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) ![Outdoor spa tub](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/1c7057e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/22ef1826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/807b3960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing [](https://www.expedia.co.uk/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information) Sherwood Forest 9.8/10 Exceptional (14 reviews) "Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew F. £289 includes taxes & fees 6 Apr - 7 Apr [](https://www.expedia.co.uk/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/0e4076ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/2e0581f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/c729995e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires! [](https://www.expedia.co.uk/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information) Sherwood Forest 10/10 Exceptional (5 reviews) "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. £280 includes taxes & fees 6 Apr - 7 Apr [](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/100000000/99250000/99243600/99243554/8de4c71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/6b5af50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/00cc85e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/43b40eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Near Tanglewood: Historic Summer Retreat [](https://www.expedia.co.uk/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information) New Lebanon 9.4/10 Exceptional (26 reviews) "Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul S. £259 includes taxes & fees 5 Apr - 6 Apr [](https://www.expedia.co.uk/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/c50e9e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/6137aab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home in Great Barrington [](https://www.expedia.co.uk/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) Great Barrington 9.8/10 Exceptional (28 reviews) "The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) maureen k. £241 includes taxes & fees 13 Apr - 14 Apr [](https://www.expedia.co.uk/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, electric kettle](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/52345b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/9af2b9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Riverside Berkshires Retreat [](https://www.expedia.co.uk/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) Great Barrington 9.2/10 Wonderful (13 reviews) "Close to a great bakery and near to a farm market and shopping mall. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cristine C. £222 includes taxes & fees 16 Apr - 17 Apr [](https://www.expedia.co.uk/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/4b325a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/f501a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-00a818b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-b25e9082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### All the comforts of home [](https://www.expedia.co.uk/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.Hotel-Information) Hudson 9.2/10 Wonderful (31 reviews) "The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia C. £119 includes taxes & fees 23 Apr - 24 Apr [](https://www.expedia.co.uk/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/bdc7550f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/a38bbe4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/811d3663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions! [](https://www.expedia.co.uk/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) Pittsfield 7.8/10 Good (7 reviews) "The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liz V. £363 includes taxes & fees 4 Apr - 5 Apr [](https://www.expedia.co.uk/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/w2439h1242x124y0-c2be86b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/d970b68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b86b4635.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b7940a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk into town, soak up sun on enclosed porch & steps away from nature trails! [](https://www.expedia.co.uk/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) Stockbridge 10/10 Exceptional (35 reviews) "A very special, well equipped, and comfortable house with a great kitchen, bedrooms and bathrooms as well as a lovely enclosed porch and outdoor area in an amazing location. Wonderful home with all amenities and thoughtful details provided for guests. A short walk to charming town and across from a beautiful hiking area. Excellent stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan £539 includes taxes & fees 4 Apr - 5 Apr [](https://www.expedia.co.uk/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/f0ba5959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/fbef3554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/23a17279.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/6d1211ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Berkshires Home Near Tanglewood, Trails & Wineries [](https://www.expedia.co.uk/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) Lebanon Springs 9.0/10 Wonderful (21 reviews) "Comfy beds, clean, great big deck with a view. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Corinne T. £287 includes taxes & fees 5 Apr - 6 Apr [](https://www.expedia.co.uk/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/665b8282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/ab946d75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/3e6e58ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/8f9296e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheerful 3-bedroom cottage with woodstove [](https://www.expedia.co.uk/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information) Sheffield 10/10 Exceptional (42 reviews) "The property was centrally located for skiing, and was a comfortable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly R. £370 includes taxes & fees 6 Apr - 7 Apr [](https://www.expedia.co.uk/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/127000000/126400000/126398500/126398409/db1d8490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/127000000/126400000/126398500/126398409/c79d5486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, Internet, bed sheets](https://images.trvl-media.com/lodging/127000000/126400000/126398500/126398409/9b4019a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/127000000/126400000/126398500/126398409/82eca24d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet [](https://www.expedia.co.uk/New-Lebanon-Hotels-NEW-Spacious-4BR-Ski-Getaway-Minutes-To-Jiminy-Bousquet.h126398409.Hotel-Information) New Lebanon £243 includes taxes & fees 3 Apr - 4 Apr [](https://www.expedia.co.uk/New-Lebanon-Hotels-NEW-Spacious-4BR-Ski-Getaway-Minutes-To-Jiminy-Bousquet.h126398409.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/w1419h960x21y0-4ecf9f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/768d59cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/34317c41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/68e2333c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Artists’ Hideaway in Old Chatham [](https://www.expedia.co.uk/Old-Chatham-Hotels-Artists-Hideaway-In-Old-Chatham.h121082559.Hotel-Information) Old Chatham £381 includes taxes & fees 13 Apr - 14 Apr [](https://www.expedia.co.uk/Old-Chatham-Hotels-Artists-Hideaway-In-Old-Chatham.h121082559.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/cd1323be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/d3c8327e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/621adf1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/25e02c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun Filled Lenox Retreat - Minutes to Tanglewood! [](https://www.expedia.co.uk/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information) Lee 9.8/10 Exceptional (6 reviews) "Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paulo I. £341 includes taxes & fees 5 Apr - 6 Apr [](https://www.expedia.co.uk/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information) ![TV, fireplace, printers](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/4d94597a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/61aeb8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/dc9a1bf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, printers](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/69c2e8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room [](https://www.expedia.co.uk/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.Hotel-Information) Great Barrington 10/10 Exceptional (4 reviews) "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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberta £997 includes taxes & fees 3 Apr - 4 Apr [](https://www.expedia.co.uk/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/9bc69856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/38d4cb32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/c41e9570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/6468f916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck [](https://www.expedia.co.uk/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122156037.Hotel-Information) Stephentown 9.0/10 Wonderful (2 reviews) "excellent communication with property manager." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy H. £410 includes taxes & fees 3 Apr - 4 Apr [](https://www.expedia.co.uk/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122156037.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/dac46480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/97c48259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/c0195267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/60aae901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hudson Hot Tub & Pet Escape [](https://www.expedia.co.uk/Hudson-Hotels-Hudson-Hot-Tub-Pet-Escape.h120658957.Hotel-Information) Stottville 10/10 Exceptional (2 reviews) £229 includes taxes & fees 6 Apr - 7 Apr [](https://www.expedia.co.uk/Hudson-Hotels-Hudson-Hot-Tub-Pet-Escape.h120658957.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/53ad91f9.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) ![Interior](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/ece4965a_edited_692a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/6f64b785_edited_9a5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable Berkshires retreat on mtn resort, SISO [](https://www.expedia.co.uk/Hancock-Hotels-Comfortable-Berkshires-Retreat-On-Mtn-Resort.h109434975.Hotel-Information) Hancock 9.0/10 Wonderful (7 reviews) "Kind and responsive host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Javier £398 includes taxes & fees 3 Apr - 4 Apr [](https://www.expedia.co.uk/Hancock-Hotels-Comfortable-Berkshires-Retreat-On-Mtn-Resort.h109434975.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711133/ba8bc3b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711133/cd7f7955.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711133/50598ac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711133/ee09debb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded escape w/ hot tub + pizza oven+ fireplace [](https://www.expedia.co.uk/Craryville-Hotels-Secluded-Escape-W-Hot-Tub-Pizza-Oven-Fireplace.h123711133.Hotel-Information) Taghkanic £716 includes taxes & fees 6 Apr - 7 Apr [](https://www.expedia.co.uk/Craryville-Hotels-Secluded-Escape-W-Hot-Tub-Pizza-Oven-Fireplace.h123711133.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/8b34823f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/9510eac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/b9c0be0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, ping pong](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/17bd9585.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5-bedroom house in charming Lee with WiFi [](https://www.expedia.co.uk/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information) Lee 8.8/10 Excellent (3 reviews) "House was clean and made our Thanksgiving great with it's size and amenities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Khalil S. £595 includes taxes & fees 9 Apr - 10 Apr [](https://www.expedia.co.uk/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/3bd0d6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/8b16599a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/399488d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/c34ecca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sweet Cozy Victorian in Housatonic. Close to everything. [](https://www.expedia.co.uk/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information) Housatonic 9.8/10 Exceptional (6 reviews) "Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl F. £217 includes taxes & fees 8 Apr - 9 Apr [](https://www.expedia.co.uk/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.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=2026-04-16&endDate=2026-04-17®ionId=173346&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=West+Stockbridge%2C+Massachusetts%2C+United+States+of+America®ionId=173346&latLong=42.333809%2C-73.36776&adults=2&startDate=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=West+Stockbridge%2C+Massachusetts%2C+United+States+of+America®ionId=173346&latLong=42.333809%2C-73.36776&adults=2&startDate=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=West+Stockbridge%2C+Massachusetts%2C+United+States+of+America®ionId=173346&latLong=42.333809%2C-73.36776&adults=2&startDate=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=APARTMENT) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=West+Stockbridge%2C+Massachusetts%2C+United+States+of+America®ionId=173346&latLong=42.333809%2C-73.36776&adults=2&startDate=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=CONDO) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=West+Stockbridge%2C+Massachusetts%2C+United+States+of+America®ionId=173346&latLong=42.333809%2C-73.36776&adults=2&startDate=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=COTTAGE) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=West+Stockbridge%2C+Massachusetts%2C+United+States+of+America®ionId=173346&latLong=42.333809%2C-73.36776&adults=2&startDate=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=VILLA) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=West+Stockbridge%2C+Massachusetts%2C+United+States+of+America®ionId=173346&latLong=42.333809%2C-73.36776&adults=2&startDate=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=CABIN) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=West+Stockbridge%2C+Massachusetts%2C+United+States+of+America®ionId=173346&latLong=42.333809%2C-73.36776&adults=2&startDate=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=CHALET) ![](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%2FWest-Stockbridge-Private-Holiday-Homes.d173346-aaPrivateHolidayHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWest-Stockbridge-Private-Holiday-Homes.d173346-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ## Top West Stockbridge Hotel Reviews ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375_y.jpg) ### Vacation Village in the Berkshires 6/10 Okay "I recently stayed in a one bedroom suite at this villa property and unfortunately the experience was disappointing, especially for business travel. When I booked the reservation, I expected the main amenities such as the clubhouse to be easily accessible. In reality, the clubhouse sits on top of a hill. While there is temporary parking directly in front of the entrance, the designated guest parking is located at the bottom of the hill. This means guests either have to walk up a steep hill or climb several flights of stairs to reach the clubhouse. This setup is very inconvenient, particularly in cold weather or when carrying items for activities like swimming. I also experienced maintenance issues in the unit. I reported a clogged faucet and maintenance came to address it, but the problem was not actually fixed. Instead, the clog appeared to shift from one side of the sink to the other, eventually causing unpleasant debris to come back up through the drain, which was unsanitary and frustrating. The location is also quite isolated with limited nearby restaurant or dining options. While the condominium setup may work for guests planning to cook, it is not ideal for business travelers who need convenience and easy access to food and services. Overall, I would not recommend this property for corporate travel." [](https://expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 8/10 Good "Room temperature was good. Breakfast coukd improve, lack of protein, muffins were not fresh. " [](https://expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "This was a very nice stay. The gentleman that checked us in was friendly, funny, knowledgeable and very welcoming. " [](https://expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "this has been absolutely amazing and incredible for incredibly difficult time for our family because of family medical emergency. everyone has been so amazing and beautiful and healing for our loved ones and we are grateful to be close to then" [](https://expedia.co.uk/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean, quiet, spacious, comfortable, and lovely furnishings! It was a very relaxing overnight." [](https://expedia.co.uk/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Quality Inn Great Barrington](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8_y.jpg) ### Quality Inn Great Barrington 8/10 Good "The Quality Inn in Great Barrington is a good value play. The room we had was clean; the staff was friendly and knowledgeable; and the heating was welcomed on this March day. Breakfast was a weak point, but the coffee was good and available throughout the day. And yes, I would stay there again. " [](https://expedia.co.uk/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg) ### Berkshires Untold 10/10 Excellent "Easy check-in, secure and clean" [](https://expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![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 "OK, the hotel needs updating, but the staff was so friendly and helpful it didn't even matter. We parked our car, walked everywhere, 2 min to the Colonial theater! Insider tip, if you buy a breakfast tix from the front desk it's less $ than paying at the restaurant. " [](https://expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5_y.jpg) ### Hotel On North 10/10 Excellent "Very clean room, friendly staff, and a feeling of being in a “fancy” hotel while still being within budget. The location was great - I enjoyed walking around and felt safe after dark. Easy walking distance from the Colonial Theater. " [](https://expedia.co.uk/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ## Find out more about West Stockbridge ## West Stockbridge Holiday Homes information | Number of reviews | 234 | | ----------------- | ----------------- | | Accommodation | 480 Holiday Homes | | Lowest Price | £119 | | Highest Price | £997 | ## Explore a world of travel with Expedia - More ways to book - [Book Holiday Homes in West Stockbridge on Expedia.com ](https://www.expedia.com/West-Stockbridge-Private-Vacation-Homes.d173346-aaPrivateVacationHomes.Travel-Guide-Accommodation)