Title: Cheshire Holiday Homes from £145: Search Holiday Homes in Cheshire | Expedia.co.uk [Cheshire Travel Guide](https://expedia.co.uk/Cheshire.dx6005398)[Hotels in Cheshire](https://expedia.co.uk/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Holiday Rentals in Cheshire](https://expedia.co.uk/Cheshire-Holiday-Rentals.d6005398.Travel-Guide-HolidayRentals)[Flights to Cheshire](https://expedia.co.uk/Cheap-Flights-To-Cheshire.d6005398.Travel-Guide-Flights)[Cheshire Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Cheshire.d6005398.Car-Hire-Guide)[Cheshire Holidays](https://expedia.co.uk/Cheshire.d6005398.Holidays-City-Breaks) ![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.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=6005398&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=6005398&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=6005398&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=6005398&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 Cheshire holiday homes ![Exterior](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/493cc38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/775a6169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/010523ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/e8d7246a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat [](https://www.expedia.co.uk/Bennington-Hotels-Cozy-Vermont-Lodge-Hot-TubStream-Private-Wifi-SatTV.h61478133.Hotel-Information) Bennington 8.6/10 Excellent (35 reviews) "The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Malika R. £207 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Bennington-Hotels-Cozy-Vermont-Lodge-Hot-TubStream-Private-Wifi-SatTV.h61478133.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) ![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) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/06261f5b.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. £260 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w907h683x58y0-59aad182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w510h683x258y0-04b5e846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, printers](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w919h683x60y0-f3238385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w507h683x259y0-1d5f8c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Getaway Cottage [](https://www.expedia.co.uk/Williamstown-Hotels-Vacation-Getaway-Or-Remote-Workschool-Location.h60763766.Hotel-Information) Williamstown 9.2/10 Wonderful (24 reviews) "We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carole S. £330 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Williamstown-Hotels-Vacation-Getaway-Or-Remote-Workschool-Location.h60763766.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) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/a133e616.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) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/0e4076ff.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. £281 includes taxes & fees 1 Apr - 2 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/101000000/100730000/100720400/100720354/eab00089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/3d81b129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/516bcaba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/296ae5ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 14mi to Mt. Snow! Arcade, Private Suite, King Bed! [](https://www.expedia.co.uk/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information) Whitingham 10/10 Exceptional (14 reviews) "Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacklyn D. £374 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/2f78aa12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/09a3de30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/08591748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/04847bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charlemont Chalet - A 15 Acre Private Retreat [](https://www.expedia.co.uk/Charlemont-Hotels-Charlemont-Chalet-Where-The-Mountains-Meet-Luxury.h121902882.Hotel-Information) Charlemont £361 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Charlemont-Hotels-Charlemont-Chalet-Where-The-Mountains-Meet-Luxury.h121902882.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/126000000/125190000/125189700/125189667/7d01424e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125190000/125189700/125189667/e9e79509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/126000000/125190000/125189700/125189667/e9ba60b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/126000000/125190000/125189700/125189667/74d8d7b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Home in Pownal VT [](https://www.expedia.co.uk/Pownal-Hotels-Cozy-Home-In-Pownal-VT.h125189667.Hotel-Information) Pownal 10/10 Exceptional (1 review) "This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jess M. £145 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Pownal-Hotels-Cozy-Home-In-Pownal-VT.h125189667.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) ![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/44aa4835.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) ### 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. £365 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/6c6cf45f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/5dc2bebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/972c3b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/e012bbab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Florida Mountain Log Cabin [](https://www.expedia.co.uk/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.Hotel-Information) Florida 10/10 Exceptional (4 reviews) "Place was super clean. Beds were comfortable. Location was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tristan e. £252 includes taxes & fees 5 Apr - 6 Apr [](https://www.expedia.co.uk/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.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) ![Dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b7940a62.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) ### 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 £541 includes taxes & fees 1 Apr - 2 Apr [](https://www.expedia.co.uk/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/9f36ff80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/8d6ee530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/fc000043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel cot, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/9751d742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5BR Berkshire Home Mins To The Mountain [](https://www.expedia.co.uk/Charlemont-Hotels-1920s-Inspired-Spacious-5-Bedroom-Home-Minutes-To-Berkshire-East.h122227227.Hotel-Information) Charlemont 10/10 Exceptional (3 reviews) "What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason F. £463 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Charlemont-Hotels-1920s-Inspired-Spacious-5-Bedroom-Home-Minutes-To-Berkshire-East.h122227227.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) ![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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/fbef3554.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. £288 includes taxes & fees 5 Apr - 6 Apr [](https://www.expedia.co.uk/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/2802a7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/20ff0e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/f0716890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/58aa3713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Barn Retreat — All-Season Escape Awaits! [](https://www.expedia.co.uk/East-Chatham-Hotels-Spectacular-Barn-With-1-Bedroom-1-Loft.h108908975.Hotel-Information) East Chatham 10/10 Exceptional (2 reviews) "Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy S. [](https://www.expedia.co.uk/East-Chatham-Hotels-Spectacular-Barn-With-1-Bedroom-1-Loft.h108908975.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) ![Interior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/34317c41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/4fb2bcba.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) ### Artists’ Hideaway in Old Chatham [](https://www.expedia.co.uk/Old-Chatham-Hotels-Artists-Hideaway-In-Old-Chatham.h121082559.Hotel-Information) Old Chatham £383 includes taxes & fees 2 Apr - 3 Apr [](https://www.expedia.co.uk/Old-Chatham-Hotels-Artists-Hideaway-In-Old-Chatham.h121082559.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) ![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) ![Dining](https://images.trvl-media.com/lodging/127000000/126400000/126398500/126398409/db949e8d.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 £244 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/New-Lebanon-Hotels-NEW-Spacious-4BR-Ski-Getaway-Minutes-To-Jiminy-Bousquet.h126398409.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) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/412632db.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 9.6/10 Exceptional (5 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. £343 includes taxes & fees 1 Apr - 2 Apr [](https://www.expedia.co.uk/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.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) ![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) ![5 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/636f9a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 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. £597 includes taxes & fees 6 Apr - 7 Apr [](https://www.expedia.co.uk/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.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) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/4be6f104.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) ![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/38d4cb32.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. £412 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) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/125328cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/212e3685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/e73deee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/e143fb83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Greylock Cabin [](https://www.expedia.co.uk/North-Adams-Hotels-True-Cabin-In-The-Woods-New-Log-Cabin-With-View-Of-Mt-Greylock.h119137863.Hotel-Information) Florida 10/10 Exceptional (6 reviews) "the hosts were great very helpful and pleasant" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ron L. £274 includes taxes & fees 16 Apr - 17 Apr [](https://www.expedia.co.uk/North-Adams-Hotels-True-Cabin-In-The-Woods-New-Log-Cabin-With-View-Of-Mt-Greylock.h119137863.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/f305b62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/597105fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/d80b29aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/037efde9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverbend Berkshire East Basecamp - 3 bedrooms available [](https://www.expedia.co.uk/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information) Charlemont 10/10 Exceptional (2 reviews) "Very nice house and the stay was unproblematic!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noah K. £357 includes taxes & fees 3 Apr - 4 Apr [](https://www.expedia.co.uk/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.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=2026-04-13&endDate=2026-04-14®ionId=6005398&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=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=CABIN) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=VACATION_HOME) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=APARTMENT) Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=APART_HOTEL) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=COTTAGE) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=CONDO) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=VILLA) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&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%2FCheshire-Private-Holiday-Homes.d6005398-aaPrivateHolidayHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Private-Holiday-Homes.d6005398-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ## Top Cheshire Hotel Reviews ![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) ![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 10/10 Excellent "Breakfast is excellent, quiet place is peaceful you can relax really well it has an Indian cuisine restaurant inside also a bar the restaurant is excellent all you request they will do it as long that they have it they will do everything is excellent to this In. Friendly staff." [](https://expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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) ![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 "Room was comfortable and quiet. Staff accommodated a request to change rooms after check-in as we discovered there was someone next door who was constantly on the phone speaking loudly in a voice that carried on something business related. Relocating us was very appreciated." [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "The hotel is a great, upscale business hotel with friendly staff and a great restaurant." [](https://expedia.co.uk/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 8/10 Good "Staff was very accommodating. Room was ok but toilet didn’t flush without the water constantly running. Shower gel, shampoo & condition bottles were all empty in the shower. Had to call for new ones. " [](https://expedia.co.uk/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "very clean and friendly staff" [](https://expedia.co.uk/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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 "Great place to enjoy with the whole family!!!" [](https://expedia.co.uk/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ## Find out more about Cheshire ## Cheshire Holiday Homes information | Number of reviews | 137 | | ----------------- | ----------------- | | Accommodation | 282 Holiday Homes | | Lowest Price | £145 | | Highest Price | £597 | ## Explore a world of travel with Expedia - More ways to book - [Book Holiday Homes in Cheshire on Expedia.com ](https://www.expedia.com/Cheshire-Private-Vacation-Homes.d6005398-aaPrivateVacationHomes.Travel-Guide-Accommodation)