Title: Hotels in Windsor, MA - Best Windsor Hotels from £52 - Fully Refundable Options - Expedia.co.uk [Holiday Rentals in Windsor](https://expedia.co.uk/Windsor-Holiday-Rentals.d6005427.Travel-Guide-HolidayRentals)[Windsor Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Windsor.d6005427.Car-Hire-Guide)[Windsor Holidays](https://expedia.co.uk/Windsor.d6005427.Holidays-City-Breaks) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.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 ## Go beyond your typical stay in Windsor Pool [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&amenities=POOL) Apart­ment [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=APARTMENT) Pet friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&amenities=PETS) Farm [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=AGRITOURISM) Cabin [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=CABIN) Family friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&travelerType=family_friendly) Hot tub [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&amenities=HOT_TUB) Condo [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=CONDO) Cottage [](https://www.expedia.co.uk/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=COTTAGE) ## Check prices for these dates Tonight [26 Feb - 27 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6005427&startDate=2026-02-26&endDate=2026-02-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [27 Feb - 28 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6005427&startDate=2026-02-27&endDate=2026-02-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6005427&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [6 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6005427&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor hotels ![Family House | Terrace/patio](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/26677985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 1 Queen Bed, Non Smoking | Individually furnished, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/182327c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/e51296ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House | Private kitchen | Fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/9e3d1bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Becket Motel [](https://www.expedia.co.uk/Becket-Hotels-Becket-Motel.h27064222.Hotel-Information) Becket 6.8/10 (60 reviews) "Comfortable stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul £108 includes taxes & fees 28 Feb - 1 Mar [](https://www.expedia.co.uk/Becket-Hotels-Becket-Motel.h27064222.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/85000000/84370000/84362200/84362148/f94cd23f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Accessible | Mountain view](https://images.trvl-media.com/lodging/85000000/84370000/84362200/84362148/caf79b73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room | In-room safe, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84370000/84362200/84362148/d0c9280e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/85000000/84370000/84362200/84362148/954b171c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Vista Motor Lodge [](https://www.expedia.co.uk/North-Adams-Hotels-Blue-Vista-Motor-Lodge.h84362148.Hotel-Information) North Adams 9.8/10 Exceptional (202 reviews) "Great stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ALEKSey £139 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/North-Adams-Hotels-Blue-Vista-Motor-Lodge.h84362148.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/4d496801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/087b92a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/bf0ac5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/75ab7331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Travel Lodge [](https://www.expedia.co.uk/Albany-Hotels-Berkshire-Travel-Lodge.h1793522.Hotel-Information) Austerlitz 5.4/10 (463 reviews) "Nice location for my needs. Breakfast was not good or healthy. A little old, but had everything I needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cameron £52 includes taxes & fees 28 Feb - 1 Mar [](https://www.expedia.co.uk/Albany-Hotels-Berkshire-Travel-Lodge.h1793522.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/d9cb5b56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 1 King Bed, Non Smoking | Egyptian cotton sheets, premium bedding, down duvets, Tempur-Pedic beds](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/8eb2abf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 1 King Bed, Non Smoking | Living area | IPod dock, MP3 dock](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/c882608e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/515036a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Kenmore Hall [](https://www.expedia.co.uk/Richmond-Hotels-Inn-At-Kenmore-Hall.h27551652.Hotel-Information) Richmond 10/10 Exceptional (27 reviews) "Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret £465 includes taxes & fees 28 Feb - 1 Mar [](https://www.expedia.co.uk/Richmond-Hotels-Inn-At-Kenmore-Hall.h27551652.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/66dde072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/59498ff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/a1e89c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/4417504a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Porches Inn at Mass MoCA [](https://www.expedia.co.uk/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) North Adams 9.4/10 Exceptional (459 reviews) "The great people!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie £135 includes taxes & fees 29 Mar - 30 Mar [](https://www.expedia.co.uk/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/4092a889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/5a448032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/d652d2fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Suite- NO PETS ALLOWED | Individually furnished, iron/ironing board, cots/infant beds](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/e75ce45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites [](https://www.expedia.co.uk/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) Pittsfield 8.6/10 Excellent (358 reviews) "Very helpful staff, clean and spacious rooms. Has everything you need - well equipped." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn £84 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/bb79982b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Private Bathroom (Field of Dreams) | Individually decorated, individually furnished, free WiFi, bed sheets](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/903dd1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/b3ee4f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/8a6408f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbour House Inn [](https://www.expedia.co.uk/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) Cheshire 9.4/10 Exceptional (53 reviews) "Nice place for a weekend away." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory £186 includes taxes & fees 9 Mar - 10 Mar [](https://www.expedia.co.uk/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/c5994ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/cfdb82a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/w488h380x9y0-567859b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/4037455f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 33 Main [](https://www.expedia.co.uk/Lenox-Hotels-33-Main.h20033760.Hotel-Information) Lenox 10/10 Exceptional (74 reviews) "Beautiful place. Wonderful owner and staff. Our stay there was a total delight." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James £379 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Lenox-Hotels-33-Main.h20033760.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/43cacb6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/cfde231b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rosalyn Elkan Suite, Cottage | Fireplace](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/01b23076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/057b9dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Terrace Inn [](https://www.expedia.co.uk/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) Lenox 9.0/10 Wonderful (43 reviews) "Comfortable bed. Quiet location. Excellent breakfast. Friendly host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen £180 includes taxes & fees 28 Feb - 1 Mar [](https://www.expedia.co.uk/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b138d836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/3a99baa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b4275c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Accessible | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/644deeee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Inn [](https://www.expedia.co.uk/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) Pittsfield 7.8/10 Good (844 reviews) "This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARIA J £69 includes taxes & fees 5 Mar - 6 Mar [](https://www.expedia.co.uk/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) ![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/7f42759d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/71df138f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/b35035ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/3f592f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jiminy Peak Mountain Resort [](https://www.expedia.co.uk/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) Hancock 8.2/10 Very good (989 reviews) "nice and clean, good customer service, but the room is smell. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Huang £156 includes taxes & fees 11 Mar - 12 Mar [](https://www.expedia.co.uk/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/5bcca6ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![28-inch TV with digital channels, Netflix, pay films](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/be3999ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, individually decorated](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/d0afa322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/2bb92acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Trail in Adams - Berkshires’ Art Hotel [](https://www.expedia.co.uk/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.Hotel-Information) Adams 9.0/10 Wonderful (144 reviews) "Staff was great, very clean, Breakfast was terrific" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael £143 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.Hotel-Information) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/27ba18f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/w696h390x1y0-dec65b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/1715f4d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/1026298b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Lenox Pittsfield [](https://www.expedia.co.uk/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) Pittsfield 9.2/10 Wonderful (668 reviews) " Nice staff - beautiful hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARY £112 includes taxes & fees 22 Mar - 23 Mar [](https://www.expedia.co.uk/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/17f29286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/20495b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Lenox [](https://www.expedia.co.uk/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) Lenox 7.6/10 Good (834 reviews) "Clean room and the bed was very comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arlan £57 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/f2737e42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/078c714a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pines Duplex Suite | Living area | 38-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/445f9562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/354e34f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Silver Maple Farm [](https://www.expedia.co.uk/East-Chatham-Hotels-Inn-At-Silver-Maple-Farm.h17094013.Hotel-Information) East Chatham 9.8/10 Exceptional (101 reviews) "Great property, very comfortable, incredible staff, easy access to skiing in the area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dominick £98 includes taxes & fees 24 Mar - 25 Mar [](https://www.expedia.co.uk/East-Chatham-Hotels-Inn-At-Silver-Maple-Farm.h17094013.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/91284a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a97806ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG [](https://www.expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) Pittsfield 8.0/10 Very good (1,000 reviews) "Staff was very courteous and rooms clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven £85 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/69e879d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/47826e47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/bd7aa934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pilates](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/c06c6b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gateways Inn & Restaurant [](https://www.expedia.co.uk/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information) Lenox 8.0/10 Very good (197 reviews) "Gateways Inn is a fantastic place to stay! The staff was very courteous and the room was spacious and very clean. The breakfast was included and very tasty. I highly suggest a stay there if you are planning on visiting the Berkshires!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miguel £154 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information) ![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/90dd9d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/83c805e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites [](https://www.expedia.co.uk/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) Pittsfield 8.6/10 Excellent (1,006 reviews) "Very friendly and good Breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesse £79 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/f0d9797c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/047ef967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/28728ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/48ee1fed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Whitlock [](https://www.expedia.co.uk/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information) Lenox 8.6/10 Excellent (290 reviews) "Super cute place and walking distance to a bunch of great shops and food! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gina £98 includes taxes & fees 4 Mar - 5 Mar [](https://www.expedia.co.uk/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information) ![55-inch LCD TV with digital channels, printers](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/0a4a8480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 King Bed (Room 4) | Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/219287f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 King Bed (Room 4) | Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/674accb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/f9501b50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Revival House [](https://www.expedia.co.uk/Adams-Hotels-The-Revival-House.h113486763.Hotel-Information) Adams 9.0/10 Wonderful (26 reviews) "Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) melissa £124 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Adams-Hotels-The-Revival-House.h113486763.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=2026-03-13&endDate=2026-03-14®ionId=6005427&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=HTG_SPRING_PROMO_6005427) ![](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%2FWindsor-Hotels.d6005427.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Hotels.d6005427.Travel-Guide-Hotels) ## Top Windsor Hotel Reviews ![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 "Room was so clean and had kitchen supplys! We enjoyed the pool and Jacuzzi tub! So close to so many ski areas and cute country stores." [](https://expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Overall pleasant stay; great facilities, staff, and location" [](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/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Very spacious and comfortable. Great for families." [](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 "Clean room nice staff" [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Affordable price, clean bedroom and close to everything. " [](https://expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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 "My wife and I just got back from a 2 night stay at the Hotel Downstreet in North Adams MA. We were very happy with this hotel and definitely plan to return! Several things stood out to us: first, upon checking in the front desk staff placed us in a quiet room located at the end of a hallway. This was very considerate, as there were numerous young families staying at this hotel (it was school vacation week). Second, our room was spotless and the bed was comfortable. The amenities at the hotel looked great - indoor pool, fitness center, and laundry (very useful if staying with young children). Location: walking distance to Mass MoCA, grocery store (Big Y), and pharmacy (CVS) and several restaurants; driving distance to attractions in the Berkshires, southern VT, and the NY capital region. And finally - an outstandingly reasonable price. Well worth a stay if you are looking for a trip in NW Massachusetts/the Berkshires." [](https://expedia.co.uk/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "Rooms were unique. Staff friendly. Pool and hot tub open late. Would come again." [](https://expedia.co.uk/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Elegant and oupdated decor throughout, spotlessly clean Welocation, " [](https://expedia.co.uk/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "convenient location, wonderful breakfast, very clean and comfortable" [](https://expedia.co.uk/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ## More cheap stays in Windsor ![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Howard Johnson by Wyndham Lenox 462 Pittsfield Rd Lenox MA £57 1 Mar - 2 Mar includes taxes & fees 7.6/10 Good! (834 reviews) [](https://expedia.co.uk/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn 170 Housatonic Street Lee MA £71 26 Mar - 27 Mar includes taxes & fees 8.4/10 Very Good! (1,000 reviews) [](https://expedia.co.uk/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Red Roof Inn PLUS+ South Deerfield – Amherst 9 Greenfield Rd South Deerfield MA £72 2 Mar - 3 Mar includes taxes & fees 7.2/10 Good! (1,005 reviews) [](https://expedia.co.uk/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Yankee, Trademark Collection by Wyndham 461 Pittsfield Rd Lenox MA £76 8 Mar - 9 Mar includes taxes & fees 9.2/10 Wonderful! (1,000 reviews) [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Berkshires-Lenox 445 Pittsfield Rd Lenox MA £92 8 Mar - 9 Mar includes taxes & fees 9.2/10 Wonderful! (1,000 reviews) [](https://expedia.co.uk/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Fairfield Inn & Suites by Marriott Williamstown](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/5d49dcf2_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Fairfield Inn & Suites by Marriott Williamstown 430 Main St Williamstown MA £112 30 Mar - 31 Mar includes taxes & fees 8.8/10 Excellent! (405 reviews) [](https://expedia.co.uk/Williamstown-Hotels-Fairfield-Inn-Suites-By-Marriott-Williamstown.h35099355.Hotel-Information) ## Frequently asked questions ### What is the best area to stay in Windsor? > This central area is the heart of Windsor, offering easy pedestrian access to many of the town's key attractions. You'll find a wide selection of shops, restaurants, and pubs here, all within a short stroll of Windsor Castle and the Long Walk. The streets are generally well-kept and easy to navigate. > > > Couples looking for a romantic getaway will find the town centre ideal. With the castle on your doorstep, charming cobbled streets, and a variety of dining options from casual to fine dining, it provides a refined and convenient base for exploring. You can easily spend your days touring the castle, enjoying a boat trip on the River Thames, or simply relaxing in one of the many cafes. > > > Families will also appreciate the convenience of staying in the town centre. Being close to the castle means less travel time with little ones, and there are several parks nearby, including Alexandra Gardens along the river, superb for children to play. ### When is the best time to go to Windsor? > Summer offers warm, pleasant weather, ideal for outdoor activities like hiking, fishing, and exploring the natural beauty of the Berkshire Mountains. The days are long, allowing ample time for sightseeing and enjoying the region's lakes and rivers. This is a great time for families looking for a relaxed holiday with plenty of fresh air and nature. > > > Early autumn brings cooler temperatures and the spectacular colours of the fall foliage. This period is particularly good for couples or solo travellers who appreciate scenic drives, photography, and outdoor adventures in a picturesque setting. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Windsor hotel booking with Expedia? ### How much is the nightly rate at a Windsor hotel? ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - More ways to book - [4 Star Hotels in Western Massachusetts ](https://www.expedia.co.uk/4Star-Western-Massachusetts-Hotels.s40-0-d6234063.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Cheshire ](https://www.expedia.co.uk/5Star-Cheshire-Hotels.s50-0-d6005398.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Worthington ](https://www.expedia.co.uk/5Star-Worthington-Hotels.s50-0-d6005428.Travel-Guide-Filter-Hotels) - [Adams Hotels ](https://www.expedia.co.uk/Adams-Hotels.d6005393.Travel-Guide-Hotels) - [Ashfield Hotels ](https://www.expedia.co.uk/Ashfield-Hotels.d3000421239.Travel-Guide-Hotels) - 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