Title: TOP Romantic Hotels in The Berkshires, MA for 2026 - The Berkshires Romantic Getaways | 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://images.trvl-media.com/place/6047665/e95ad08c-cd3f-48ea-b01c-31171bbd50b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Photo courtesy of Berkshire Visitors Bureau ![](https://images.trvl-media.com/place/6047665/e95ad08c-cd3f-48ea-b01c-31171bbd50b7.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 availability on The Berkshires Romantic Hotels Tonight [21 Jan - 22 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2026-01-21&endDate=2026-01-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [22 Jan - 23 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2026-01-22&endDate=2026-01-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [23 Jan - 25 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [30 Jan - 1 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for The Berkshires romantic hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/dbcc78d8.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) ![Indoor pool, seasonal outdoor pool, pool loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3f4a1adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham [](https://www.expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) Lenox 9.2/10 Wonderful (1,008 reviews) "The hotel is very nice and clean. From the moment we checked in to check out, we had an amazing time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gina £77 includes taxes & fees 28 Jan - 29 Jan [](https://www.expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/6a569eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold [](https://www.expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) Lenox 9.0/10 Wonderful (842 reviews) "So charming, clean, thoughtful touches and a really special place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juliana £73 includes taxes & fees 22 Jan - 23 Jan [](https://www.expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/83421694.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 £82 includes taxes & fees 23 Jan - 24 Jan [](https://www.expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Front of property – evening/night](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/1ea731f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic Area](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/30e56504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/f3e43c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Williams Inn [](https://www.expedia.co.uk/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) Williamstown 9.6/10 Exceptional (564 reviews) "Great stay. Comfortable hotel and very friendly staff. Restaurant is very good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronica £147 includes taxes & fees 28 Jan - 29 Jan [](https://www.expedia.co.uk/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3e2d816d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/94cb14a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property – evening/night](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/4e4268ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn [](https://www.expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) Stockbridge 8.8/10 Excellent (1,003 reviews) "All was great! The atmosphere, food, and rooms were very clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brent £157 includes taxes & fees 25 Jan - 26 Jan [](https://www.expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/6d6c1dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/c08e3534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/3bd826d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/8bcde002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gedney Farm [](https://www.expedia.co.uk/Great-Barrington-Hotels-Gedney-Farm.h41178000.Hotel-Information) Great Barrington 9.2/10 Wonderful (134 reviews) "We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynda £151 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Great-Barrington-Hotels-Gedney-Farm.h41178000.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/6f32fa47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/3670f3af.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) ![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) ### 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 £159 includes taxes & fees 27 Jan - 28 Jan [](https://www.expedia.co.uk/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) ![Suite, Private Bathroom (RedBird Suite) | View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast ](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/w3000h1988x0y3-ae06d912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Parlour Suite) | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/d4b17f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/5312662c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood [](https://www.expedia.co.uk/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) Stockbridge 9.2/10 Wonderful (110 reviews) "Great breakfast, friendly helpful staff, pretty yard, good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah £279 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/614a1cdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/0ab1624d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/9ad8b813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/afbb4318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Village Carriage House - Super Private!! [](https://www.expedia.co.uk/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) Lanesborough 9.8/10 Exceptional (272 reviews) "It was a cute property- just what we needed. Nice location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda M. £158 includes taxes & fees 23 Jan - 24 Jan [](https://www.expedia.co.uk/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/74000000/73070000/73062200/73062141/857eb070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73070000/73062200/73062141/w1008h683x16y0-86131c43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73070000/73062200/73062141/2d6ee5bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73070000/73062200/73062141/ad9e5cfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn [](https://www.expedia.co.uk/Hancock-Hotels-Deluxe-Yeti-Suite-On-Jiminy-Mtn-1st-Flr-Sleeps-4-New-Fully-Redone-Country-Inn.h73062141.Hotel-Information) Hancock 9.8/10 Exceptional (22 reviews) "Great place to spend the new years holiday! Perfect location for skiing!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexandra D. £207 includes taxes & fees 22 Jan - 23 Jan [](https://www.expedia.co.uk/Hancock-Hotels-Deluxe-Yeti-Suite-On-Jiminy-Mtn-1st-Flr-Sleeps-4-New-Fully-Redone-Country-Inn.h73062141.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=2026-02-04&endDate=2026-02-05®ionId=6047665&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Find out more about The Berkshires ### The Berkshires attractions for couples The Berkshires is a paradise of experiences waiting to be explored. Start your adventure at the renowned Tanglewood Music Center, where you can enjoy a summer concert by the Boston Symphony Orchestra amidst the stunning natural backdrop. For art enthusiasts, the Massachusetts Museum of Contemporary Art (MASS MoCA) is a must-visit, showcasing groundbreaking installations and performances in a former mill turned vibrant art hub. Families will delight in a day at the Berkshire Museum, where interactive exhibits and a diverse aquarium offer fun for all ages. Outdoor lovers can hike the picturesque trails of Mount Greylock, the highest peak in Massachusetts, breathtaking panoramic views and well-maintained paths suitable for all skill levels. After a day of exploration, unwind in the charming town of Lenox, known for its luxurious accommodations like the historic Cranwell Spa & Golf Resort. With its elegant rooms and top spa services, it’s the perfect base for a comfortable stay while you delve into the region's rich culture and natural beauty. The Berkshires promises a delightful blend of artistic flair and outdoor adventure, ensuring memorable experiences for the entire family. ## Top The Berkshires Hotel Reviews ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Absolutely fabulous!" [](https://expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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 "Wow. This hotel is such a great find. Not only is it clean and unique, the rooms are large and the staff are super helpful and nice. Breakfast was nice. The pool was slightly colder than I expected but it was 5 degrees outside and windy so its understandable. The hot tub was very comfortable. I would love to stay here again. My kids said this is their favorite hotel we have ever stayed at which is high praise since we travel frequently and have stayed in a ton of hotels!" [](https://expedia.co.uk/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ## 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) - [Hotels near Animagic Museum of Animation ](https://www.expedia.co.uk/Animagic-Museum-Of-Animation-Hotels.0-l553248621560926701-0.Travel-Guide-Filter-Hotels) - [Becket Hotels ](https://www.expedia.co.uk/Becket-Hotels.d6005395.Travel-Guide-Hotels) - [Blandford Hotels ](https://www.expedia.co.uk/Blandford-Hotels.d80625.Travel-Guide-Hotels) - 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