Title: TOP Hotels with Connecting Rooms in The Berkshires, MA for 2025 | Expedia.co.uk [The Berkshires Travel Guide](https://expedia.co.uk/The-Berkshires.dx6047665)[Hotels in The Berkshires](https://expedia.co.uk/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[Holiday Rentals in The Berkshires](https://expedia.co.uk/The-Berkshires-Holiday-Rentals.d6047665.Travel-Guide-HolidayRentals)[Flights to The Berkshires](https://expedia.co.uk/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-The-Berkshires.d6047665.Car-Hire-Guide)[The Berkshires Holidays](https://expedia.co.uk/The-Berkshires.d6047665.Holidays-City-Breaks) ![The Berkshires featuring flowers](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/71000/71831-The-Berkshires.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Hotels with Connecting Rooms in The Berkshires ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on The Berkshires Hotels with Connecting Rooms Tonight [24 Oct - 25 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [25 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [24 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [31 Oct - 2 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top The Berkshires Hotels with Connecting Rooms ![Front of property – evening/night](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/9e766351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds | Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/651f878e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c3ea2282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel On North Pittsfield 9.6/10 Exceptional (786) "Nice hotel. Very friendly and professional staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Magen £82 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Pittsfield-Hotels-Hotel-On-North.h10246103.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.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/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (917) "Enjoyable stay. Staff were very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claire £86 includes taxes & fees 8 Nov - 9 Nov [](https://www.expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillow-top beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/11bb9318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/62ab3ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG Great Barrington 8.8/10 Excellent (678) "This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tina £85 includes taxes & fees 13 Nov - 14 Nov [](https://www.expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One King Bed, Non-Smoking, Accessible | View from room](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/5d049cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 8:00 AM to 10:00 PM, pool loungers](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/ceca8706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/e55e7242.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Berkshires-Lenox Lenox 9.2/10 Wonderful (1003) "Very clean, nice amenities , great location!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin £93 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Fireplace | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f43c89bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham Lenox 9.0/10 Wonderful (1018) "Good breakfast King rooms are the best facing the mountains Recently remodeled " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan M £106 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Non Lakeside Superior Room, 2 Queen beds | Premium bedding, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.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) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel Lee 9.2/10 Wonderful (1004) "Great Indian restaurant in the hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris £89 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun deck](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a02c1cad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 Queen Bed | Living area | TV](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/d32c867e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 King Bed | 1 bedroom, individually decorated, individually furnished](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/f3a87415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cornell Inn, Lenox & The Berkshires Lenox 9.0/10 Wonderful (1000) "Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob £136 includes taxes & fees 27 Oct - 28 Oct [](https://www.expedia.co.uk/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![Hypo-allergenic bedding, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216.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/1000000/10000/3000/2943/433bbf3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/5e762248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 6:00 AM to 10 PM, pool loungers](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/ecbe7d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Downstreet, an Ascend Collection Hotel North Adams 8.8/10 Excellent (1002) "Staff was very nice!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David £120 includes taxes & fees 20 Nov - 21 Nov [](https://www.expedia.co.uk/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/5fa17ca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/507a7437.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch LCD TV with cable/satellite TV channels, TV, MP3 dock](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/8f88194e.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) ### Hilton Garden Inn Lenox Pittsfield Pittsfield 9.2/10 Wonderful (653) "Nice quiet hotel, easy in and out, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard £107 includes taxes & fees 16 Nov - 17 Nov [](https://www.expedia.co.uk/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/9d0420c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/32c535e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/f2aaf746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires Great Barrington 9.4/10 Exceptional (745) "The property is very nice and the staff was extremely friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg £120 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2025-11-07&endDate=2025-11-08®ionId=6047665&adults=2&room_amenities_group_explore=connecting_rooms_available&sort=RECOMMENDED&openPlayBack=true) ## Top The Berkshires Hotel Reviews ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "In a very nice annex suite." [](https://expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well. " [](https://expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Staff was very welcoming and friendly! They provided great tips on restaurants and things to do in are." [](https://expedia.co.uk/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Great stay-- would stay here again-- safe, nice welcome from Cameron at front desk, room was clean and cozy. Bed was very comfortable. Didn't have breakfast. I usually stay in Pittsfield at a hotel that has given me a discount since March when my mother was put into a nursing home. I normally try to come down twice a month from CNY--needless to say it is expensive for me.. Random question-- do you offer discounts?" [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Felt comfortable and safe. Nice pool and gym facility." [](https://expedia.co.uk/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ## Frequently asked questions ### How much do hotels with connecting rooms in The Berkshires cost? > You can expect to pay from to per night for hotels with connecting rooms in The Berkshires. Whatever your budget, you'll find the perfect stay on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### What are the best hotels with connecting rooms in The Berkshires? > The Berkshires has multiple hotels with connecting rooms, with a total average guest review rating of . Organising an escape to Lenox? Put your bags down at [Hotel On North](https://www.expedia.co.uk/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information), a popular 3.5-star option with mountain views and a restaurant. Another highly recommended choice with connecting rooms is [Hilton Garden Inn Lenox Pittsfield](https://www.expedia.co.uk/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information). It has a 3-star rating and conveniences that include a terrace and a swimming pool. ### How many hotels with adjoining rooms are there in The Berkshires? > The Berkshires has hotels with adjoining rooms on offer. Enter your destination and travel dates and book your ideal holiday today. ### What are the top motels with connecting rooms in The Berkshires? > Providing guests with extra space and convenience, motels with connecting rooms in The Berkshires are a budget-friendly way to holiday with your whole crew. If you're eager to visit Williamstown, book a few days at [Willows Motel Williamstown](https://www.expedia.co.uk/Williamstown-Hotels-Willows-Motel-Williamstown.h1753359.Hotel-Information). It's 1 mi southeast of downtown and includes amenities like a garden and a terrace. Another top pick is [Williamstown Motel](https://www.expedia.co.uk/Williamstown-Hotels-Williamstown-Motel.h2758858.Hotel-Information). It has a barbecue grill and individually decorated rooms and is located about 1 mi southeast of the centre of Williamstown.There are plenty of things to keep you entertained in Williamstown. [Williamstown Theatre Festival](https://www.expedia.co.uk/Williamstown-Theatre-Festival-Williamstown.d553248621532665542.Vacation-Attraction) and [Sterling and Francine Clark Art Institute](https://www.expedia.co.uk/Sterling-And-Francine-Clark-Art-Institute-Williamstown.d6091835.Vacation-Attraction) are two great places to start. ### Are there any family-friendly hotels with connecting rooms in The Berkshires? > There sure are, so gather the family and start planning that trip to The Berkshires! If Lenox is on your travel itinerary, stay at [Hotel On North](https://www.expedia.co.uk/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information). This 3.5-star option is a favourite family-friendly hotel with connecting rooms. It also comes with room service and housekeeping services. Another excellent choice is [Hilton Garden Inn Lenox Pittsfield](https://www.expedia.co.uk/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information). Also in Lenox, it has a 3-star rating and comes with housekeeping services, laundry facilities and connecting rooms. Lenox has tons of family-friendly attractions when you're ready to sightsee. [Hancock Shaker Village](https://www.expedia.co.uk/Hancock-Shaker-Village-Pittsfield.d6091849.Attraction) and [Berkshire Museum](https://www.expedia.co.uk/Berkshire-Museum-Pittsfield.d553248621532665288.Attraction) will keep your crew entertained. ### Why book your hotel with connecting rooms in The Berkshires with Expedia? > Booking a hotel with connecting rooms in The Berkshires is as simple as clicking on your travel dates and picking an option that meets your requirements. After something luxurious or low cost, or a stay that also includes free WiFi? Use Expedia's search filters to further narrow your search results and find the perfect fit. ### How can I find cheap hotels with connecting rooms in The Berkshires? > Expedia can help you narrow your search for cheap hotels with connecting rooms in The Berkshires. To reserve the perfect stay in a matter of clicks, try out our convenient filter tool to tailor your search results by star rating, amenities and budget. ### What is there to do in The Berkshires near my hotel with connecting rooms? > Whatever you're into, there are almost endless things to put on your to-do list in The Berkshires. If you're holidaying in Williamstown, be sure to look around [Sterling and Francine Clark Art Institute](https://www.expedia.co.uk/Sterling-And-Francine-Clark-Art-Institute-Williamstown.d6091835.Vacation-Attraction), [Williams College Museum of Art](https://www.expedia.co.uk/Williams-College-Museum-Of-Art-Williamstown.d6091837.Vacation-Attraction) and [Hopkins Observatory](https://www.expedia.co.uk/Hopkins-Observatory-Williamstown.d6091831.Vacation-Attraction). Escaping to Pittsfield? [Bousquet Ski Area](https://www.expedia.co.uk/Bousquet-Ski-Area-Pittsfield.d553248621532665283.Vacation-Attraction), [Barrington Stage Company](https://www.expedia.co.uk/Barrington-Stage-Company-Pittsfield.d553248621532665294.Vacation-Attraction) and [Berkshire Museum](https://www.expedia.co.uk/Berkshire-Museum-Pittsfield.d553248621532665288.Vacation-Attraction) are some major attractions here. ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - More ways to book - [3 Star Hotels in Great Barrington](https://www.expedia.co.uk/3Star-Great-Barrington-Hotels.s30-0-d110336.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Chester](https://www.expedia.co.uk/4Star-Chester-Hotels.s40-0-d6005399.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Great Barrington](https://www.expedia.co.uk/4Star-Great-Barrington-Hotels.s40-0-d110336.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Great Barrington](https://www.expedia.co.uk/5Star-Great-Barrington-Hotels.s50-0-d110336.Travel-Guide-Filter-Hotels) - 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