Title: Book the Best Pittsfield WINERY Hotels in 2026 | Expedia.ca [Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d9478.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d9478.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d9478.Destination-Travel-Guides) ![Pittsfield showing a city](https://images.trvl-media.com/place/9478/b5f5430c-dc51-405d-9103-478c33e1bf14.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Pittsfield, MA from CA $153 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Pittsfield Winery Hotels Tonight [Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-12-26&endDate=2025-12-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-12-27&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pittsfield hotels with winery ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/4fd790fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) Lee 9.0/10 Wonderful (1000) "Room was clean and the staff was super friendly and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ethan CA $137 CA $153 total includes taxes & fees Jan 15 - Jan 16, 2026 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Private kitchen](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/61ae6bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/22135a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/fbd2cba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Rock Inn [](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) Great Barrington 9.4/10 Exceptional (36) "We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $167 CA $187 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/ecdea449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/4bbc4f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/83d3f833_edited_d758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake! [](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information) Sherwood Forest 10/10 Exceptional (5) "We loved it! Lots of local hiking trails and a wonderful relaxing place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon K. CA $199 CA $511 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/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/1000000/900000/894100/894066/78b361f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/16c514f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/5e7062a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Triple Room](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/648d8aa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Valley Inn [](https://www.expedia.ca/Williamstown-Hotels-Berkshire-Valley-Inn.h894066.Hotel-Information) Williamstown 9.2/10 Wonderful (564) "We had a short but pleasant stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott CA $171 CA $191 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Williamstown-Hotels-Berkshire-Valley-Inn.h894066.Hotel-Information) ![Loft, Private Bathroom (Skylight Loft)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/48ea2807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Tanglewood Suite)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/c348a91f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/86910798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/eb4406db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Farm Inn [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information) Lenox 9.4/10 Exceptional (164) "Everything was perfect - location and accommodation." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information) ![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/85000000/84360000/84357600/84357520/6d1211ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/f0ba5959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/65181381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Berkshires Home Near Tanglewood, Trails & Wineries [](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) Lebanon Springs 8.8/10 Excellent (20) "It was great - just what we were looking for. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kaye S. CA $185 CA $508 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) ![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) ![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/c3446830.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.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information) New Lebanon 9.4/10 Exceptional (23) "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. CA $265 CA $607 total includes taxes & fees Dec 27 - Dec 28 [](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/9eeeead4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/6873f6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/w1424h960x16y0-bffb2a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/4f2c31bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy. Clean. Free bagel shop. 3 Fireplaces. [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.Hotel-Information) Great Barrington 10/10 Exceptional (1) "The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary R. CA $465 CA $803 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/e9c2fca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/8250863a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/930055e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/b7039a07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer [](https://www.expedia.ca/Great-Barrington-Hotels-Close-To-Tanglewood-2BR-King-Bed-Fireplace-Sleeps-6-Mountain-View-Gem.h103845853.Hotel-Information) Great Barrington CA $615 CA $774 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Great-Barrington-Hotels-Close-To-Tanglewood-2BR-King-Bed-Fireplace-Sleeps-6-Mountain-View-Gem.h103845853.Hotel-Information) ![Room (King Room)](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/b5aaacce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/ed32e5ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/1274c274.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) ### Gateways Inn & Restaurant [](https://www.expedia.ca/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information) Lenox 8.0/10 Very good (193) "Very well kept property, nice restaurant and is in a great area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Josephine CA $219 CA $256 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-09&endDate=2026-01-10®ionId=9478&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield Hotel Reviews ![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 "Wonderful breakfast, amazing relaxing hot tub, Beautiful clean room, staff friendly very helpful. Will stay again !!" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Loved having coffee and tea 24/7" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [B&B in Berkshire County ](https://www.expedia.ca/Berkshire-County-Bed-And-Breakfast.d553248635083901436-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Berkshire County ](https://www.expedia.ca/Berkshire-County-Chalets.d553248635083901436-aaChalets.Travel-Guide-Accommodation) - [Inns in Berkshire County ](https://www.expedia.ca/Berkshire-County-Inns.d553248635083901436-aaInns.Travel-Guide-Accommodation) - [Resorts in Berkshire County ](https://www.expedia.ca/Berkshire-County-Resort-Hotels.d553248635083901436-aaResortHotels.Travel-Guide-Accommodation) - [Aparthotels in Dalton ](https://www.expedia.ca/Dalton-Apart-Hotels.d6911-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Dalton ](https://www.expedia.ca/Dalton-Bed-And-Breakfast.d6911-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Dalton ](https://www.expedia.ca/Dalton-Hotels-Cheap-Hotels.0-0-d6911-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Dalton ](https://www.expedia.ca/Dalton-Hotels-Family-Hotel.0-0-d6911-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Dalton ](https://www.expedia.ca/Dalton-Hotels-Spa-Hotel.0-0-d6911-tSpaHotel.Travel-Guide-Filter-Hotels) - [Dalton Hotels ](https://www.expedia.ca/Dalton-Hotels.d6911.Travel-Guide-Hotels) - [Lodges in Dalton ](https://www.expedia.ca/Dalton-Lodges.d6911-aaLodges.Travel-Guide-Accommodation) - [Motels in Dalton ](https://www.expedia.ca/Dalton-Motels.d6911-aaMotels.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Berkshire County ](https://www.expedia.ca/Destinations-In-Berkshire-County-Beach-Hotel.0-0-d553248635083901436-tBeachHotel.Hotel-Filter-Destinations) - [Hotels with a Pool in Berkshire County ](https://www.expedia.ca/Destinations-In-Berkshire-County-Hotel-With-Pool.0-0-d553248635083901436-tHotelwithPool.Hotel-Filter-Destinations) - [Luxury Hotels in Berkshire County ](https://www.expedia.ca/Destinations-In-Berkshire-County-Luxury-Hotel.0-0-d553248635083901436-tLuxuryHotel.Hotel-Filter-Destinations) - [Pet-Friendly Hotels in Berkshire County ](https://www.expedia.ca/Destinations-In-Berkshire-County-Pet-Friendly-Hotel.0-0-d553248635083901436-tPetfriendlyHotel.Hotel-Filter-Destinations) - [Ski Hotels in Berkshire County ](https://www.expedia.ca/Destinations-In-Berkshire-County-Ski-Hotel.0-0-d553248635083901436-tSkiHotel.Hotel-Filter-Destinations) - [Berkshire County Hotels ](https://www.expedia.ca/Destinations-In-Berkshire-County.d553248635083901436.Hotel-Destinations) - [Hotels with Early Check-in in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Hotel-With-Early-Check-In.0-0-d223-thotelwithearlycheckin.Hotel-Filter-Destinations) - [Hotels with a Lazy River in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Hotels-With-A-Lazy-River.0-0-d223-tHotelswithaLazyRiver.Hotel-Filter-Destinations) - [Hotels with Free Breakfast in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Hotels-With-Free-Breakfast.0-0-d223-tHotelswithFreeBreakfast.Hotel-Filter-Destinations) - [Mountain Hotels in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Mountain-Hotels.0-0-d223-tMountainHotels.Hotel-Filter-Destinations) - [Scuba Diving Hotels in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Scuba-Diving-Vacations.0-0-d223-tscubadivingvacations.Hotel-Filter-Destinations) - [Farmstay in Hancock ](https://www.expedia.ca/Hancock-Agritourism.d112303-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Hancock ](https://www.expedia.ca/Hancock-Apart-Hotels.d112303-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Hancock ](https://www.expedia.ca/Hancock-Bed-And-Breakfast.d112303-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Rentals in Hancock ](https://www.expedia.ca/Hancock-Condos.d112303-aaCondos.Travel-Guide-Accommodation) - [Guest Houses in Hancock ](https://www.expedia.ca/Hancock-Guest-Houses.d112303-aaGuestHouses.Travel-Guide-Accommodation) - [Boutique Hotels in Hancock ](https://www.expedia.ca/Hancock-Hotels-Boutique-Hotel.0-0-d112303-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Hancock ](https://www.expedia.ca/Hancock-Hotels-Cheap-Hotels.0-0-d112303-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Hancock ](https://www.expedia.ca/Hancock-Hotels-Historic-Hotel.0-0-d112303-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Hancock ](https://www.expedia.ca/Hancock-Hotels-Luxury-Hotel.0-0-d112303-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Hancock ](https://www.expedia.ca/Hancock-Hotels-Mountain-Hotels.0-0-d112303-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Hancock ](https://www.expedia.ca/Hancock-Hotels-Pet-Friendly-Hotel.0-0-d112303-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Hancock Hotels ](https://www.expedia.ca/Hancock-Hotels.d112303.Travel-Guide-Hotels) - [Inns in Hancock ](https://www.expedia.ca/Hancock-Inns.d112303-aaInns.Travel-Guide-Accommodation) - [Resorts in Hancock ](https://www.expedia.ca/Hancock-Resort-Hotels.d112303-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Hancock Shaker Village ](https://www.expedia.ca/Hancock-Shaker-Village-Hotels.0-l6091849-0.Travel-Guide-Filter-Hotels) - [Guest Houses in Hinsdale ](https://www.expedia.ca/Hinsdale-Guest-Houses.d6005406-aaGuestHouses.Travel-Guide-Accommodation) - [Luxury Hotels in Hinsdale ](https://www.expedia.ca/Hinsdale-Hotels-Luxury-Hotel.0-0-d6005406-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Hinsdale ](https://www.expedia.ca/Hinsdale-Hotels-Spa-Hotel.0-0-d6005406-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hinsdale Hotels ](https://www.expedia.ca/Hinsdale-Hotels.d6005406.Travel-Guide-Hotels) - [Hotels near Jiminy Peak Mountain Resort ](https://www.expedia.ca/Jiminy-Peak-Mountain-Resort-Hotels.0-l553248621532665536-0.Travel-Guide-Filter-Hotels) - [Guest Houses in Lanesborough ](https://www.expedia.ca/Lanesborough-Guest-Houses.d6005408-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Lanesborough ](https://www.expedia.ca/Lanesborough-Hotels-Cheap-Hotels.0-0-d6005408-tCheapHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in Lanesborough ](https://www.expedia.ca/Lanesborough-Hotels-Spa-Hotel.0-0-d6005408-tSpaHotel.Travel-Guide-Filter-Hotels) - [Lanesborough Hotels ](https://www.expedia.ca/Lanesborough-Hotels.d6005408.Travel-Guide-Hotels) - [Inns in Lanesborough ](https://www.expedia.ca/Lanesborough-Inns.d6005408-aaInns.Travel-Guide-Accommodation) - [Vacation Homes in Lanesborough ](https://www.expedia.ca/Lanesborough-Private-Vacation-Homes.d6005408-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Aparthotels in Lenox ](https://www.expedia.ca/Lenox-Apart-Hotels.d8587-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Lenox ](https://www.expedia.ca/Lenox-Bed-And-Breakfast.d8587-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Castles in Lenox ](https://www.expedia.ca/Lenox-Castles.d8587-aaCastles.Travel-Guide-Accommodation) - [Chalets in Lenox ](https://www.expedia.ca/Lenox-Chalets.d8587-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Lenox ](https://www.expedia.ca/Lenox-Guest-Houses.d8587-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Lenox ](https://www.expedia.ca/Lenox-Holiday-Parks.d8587-aaHolidayParks.Travel-Guide-Accommodation) - [Adults Only Resorts & in Lenox ](https://www.expedia.ca/Lenox-Hotels-Adults-Only-Resorts.0-0-d8587-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Beach-Hotel.0-0-d8587-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Boutique-Hotel.0-0-d8587-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Cheap-Hotels.0-0-d8587-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Family-Hotel.0-0-d8587-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Historic-Hotel.0-0-d8587-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Lenox ](https://www.expedia.ca/Lenox-Hotels-Honeymoon-Hotels.0-0-d8587-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Lenox ](https://www.expedia.ca/Lenox-Hotels-Hotels-With-Indoor-Pool.0-0-d8587-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-LGBT-Friendly-Hotel.0-0-d8587-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Luxury-Hotel.0-0-d8587-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Romantic-Hotel.0-0-d8587-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Spa-Hotel.0-0-d8587-tSpaHotel.Travel-Guide-Filter-Hotels) - [Lenox Hotels ](https://www.expedia.ca/Lenox-Hotels.d8587.Travel-Guide-Hotels) - [Inns in Lenox ](https://www.expedia.ca/Lenox-Inns.d8587-aaInns.Travel-Guide-Accommodation) - [Resorts in Lenox ](https://www.expedia.ca/Lenox-Resort-Hotels.d8587-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Mount Greylock State Reservation Visitor Center ](https://www.expedia.ca/Mount-Greylock-State-Reservation-Visitor-Center-Hotels.0-l6272782-0.Travel-Guide-Filter-Hotels) - [Hotels near Pittsfield Station ](https://www.expedia.ca/Pittsfield-Station-Hotels.d6195403.Travel-Guide-Hotels) - [Motels in Pittsfield Station ](https://www.expedia.ca/Pittsfield-Station-Motels.d6195403-aaMotels.Travel-Guide-Accommodation) - [Aparthotels in Richmond ](https://www.expedia.ca/Richmond-Apart-Hotels.d151138-aaApartHotels.Travel-Guide-Accommodation) - [Chalets in Richmond ](https://www.expedia.ca/Richmond-Chalets.d151138-aaChalets.Travel-Guide-Accommodation) - [Holiday Park Resorts in Richmond ](https://www.expedia.ca/Richmond-Holiday-Parks.d151138-aaHolidayParks.Travel-Guide-Accommodation) - [Richmond Hotels ](https://www.expedia.ca/Richmond-Hotels.d151138.Travel-Guide-Hotels) - [Hotels near Tanglewood Music Center ](https://www.expedia.ca/Tanglewood-Music-Center-Hotels.0-l503292-0.Travel-Guide-Filter-Hotels) - [Hotels near Ventfort Hall Mansion and Gilded Age Museum ](https://www.expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Hotels.0-l553248621532665270-0.Travel-Guide-Filter-Hotels) - [Flights to Lenox ](https://www.expedia.ca/Cheap-Flights-To-Lenox.d8587.Travel-Guide-Flights) - [Flights from Lenox ](https://www.expedia.ca/lp/flights/8587/flights-from-lenox) - [Flights from Bangor (BGR) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/bgr/psf/bangor-to-pittsfield) - [Flights from Boston (BOS) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/bos/psf/boston-to-pittsfield) - [Flights from Ithaca (ITH) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/ith/psf/ithaca-to-pittsfield) - [Flights from Plattsburgh (PBG) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/pbg/psf/plattsburgh-to-pittsfield) - [Flights from Phoenix (PHX) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/phx/psf/phoenix-to-pittsfield) - [Flights from Richmond (RIC) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/ric/psf/richmond-to-pittsfield) - [Flights from Seattle (SEA) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/sea/psf/seattle-to-pittsfield) - [Flights from Toronto (YYZ) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/yyz/psf/toronto-to-pittsfield) - [Canoe Meadows Wildlife Sanctuary ](https://www.expedia.ca/Canoe-Meadows-Wildlife-Sanctuary-Pittsfield.d553248621532665285.Vacation-Attraction) - [Hancock Shaker Village ](https://www.expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction) - [Lenox Library ](https://www.expedia.ca/Lenox-Library-Lenox.d553248621532665268.Vacation-Attraction) - [Richmond Vacations ](https://www.expedia.ca/Richmond.d151138.Destination-Travel-Guides) - [Ventfort Hall Mansion and Gilded Age Museum ](https://www.expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction) - [Avis Rental Cars in Lenox ](https://www.expedia.ca/Avis-Car-Rentals-In-Lenox.d8587-c41.Car-Rental-Guide-Suppliers) - [Car rental Hancock ](https://www.expedia.ca/Car-Rentals-In-Hancock.d112303.Car-Rental-Guide) - [Car rentals near Jiminy Peak Mountain Resort ](https://www.expedia.ca/Car-Rentals-In-Jiminy-Peak-Mountain-Resort.d553248621532665536.Car-Rental-Guide) - [Car rental Lenox ](https://www.expedia.ca/Car-Rentals-In-Lenox.d8587.Car-Rental-Guide) - [Rental cars Pittsfield Municipal airport ](https://www.expedia.ca/Car-Rentals-In-Pittsfield-Municipal.d6031274.Car-Rental-Guide) - [Dalton Vacation Rentals ](https://www.expedia.ca/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals) - [Book Winery Hotels in Pittsfield on Expedia.com ](https://www.expedia.com/Pittsfield-Hotels-Winery-Hotel.0-0-d9478-tWineryHotel.Travel-Guide-Filter-Hotels)