Title: Book the Best ROMANTIC Hotels in The Berkshires, MA - The Berkshires Romantic Getaways | Expedia.ca [The Berkshires Travel Guide](https://expedia.ca/The-Berkshires.dx6047665)[Hotels in The Berkshires](https://expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[Vacation Rentals in The Berkshires](https://expedia.ca/The-Berkshires-Vacation-Rentals.d6047665.Travel-Guide-VacationRentals)[Flights to The Berkshires](https://expedia.ca/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Car Rentals](https://expedia.ca/Car-Rentals-In-The-Berkshires.d6047665.Car-Rental-Guide)[The Berkshires Vacation Packages](https://expedia.ca/The-Berkshires.d6047665.Destination-Travel-Guides) ![The Berkshires which includes flowers](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/71000/71831-The-Berkshires.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in The Berkshires, MA ![](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 The Berkshires Romantic Hotels Tonight [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top The Berkshires Romantic Hotels ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.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 drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a25612d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (930) "Friendly staff and clean rooms. Loved the onsite restaurant & bar." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carmen CA $144 CA $160 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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) ![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f3c92221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.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 (1021) "Fresh breakfast menu, clean and great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gail CA $149 CA $167 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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) ![Lobby](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/f3e43c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/d48c4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/c60f19d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Williams Inn Williamstown 9.6/10 Exceptional (530) "Nice place to stay for a wedding " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy CA $275 CA $307 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d969459c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Firehouse)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds (Main Inn)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1022) "Picture perfect Inn" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jeff CA $195 CA $281 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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) ![Room, Private Bathroom (Victorian Room)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/49947e81.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) ![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) ### Brook Farm Inn Lenox 9.4/10 Exceptional (162) "Comfortable, quiet, convenient location, very friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $219 CA $244 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/663f69c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/7b669948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed (Dewey Carriage House Inn)](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/468cf971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/w2880h1917x0y0-550a94f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Constance by the Lenox Collection Lenox 8.4/10 Very good (557) "Everything was very nice. A very simple experience." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $137 CA $153 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Lenox-Hotels-Rookwood-Inn.h4945461.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) ![Garden](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/985aaf3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, garden views ](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/720e4e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, individually furnished, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/3c75b29c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gedney Farm Great Barrington 9.2/10 Wonderful (131) "Great property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Blair CA $262 CA $334 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Great-Barrington-Hotels-Gedney-Farm.h41178000.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/17dab433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/3ff5efd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/bc78d43e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/5fa6f6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whistler's Inn Bed & Breakfast Lenox 7.8/10 Good (500) "We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $213 CA $238 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Lenox-Hotels-Whistlers-Inn-Bed-Breakfast.h1197581.Hotel-Information) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/8c4366ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/614a1cdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/4e933c7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Village Carriage House - Super Private!! Lanesborough 9.8/10 Exceptional (263) "We enjoyed our stay. Excellent location to explore Western Mass!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles D. CA $188 CA $293 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73070000/73062200/73062141/abe6ba24.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) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73070000/73062200/73062141/e6beff93_edited_6ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/74000000/73070000/73062200/73062141/e162ca99.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 Hancock 9.8/10 Exceptional (20) "The condo was clean and well located for easy access to the mountain. We were there for tri-state races and having easy acass to the mountain was exactly what we needed for a fun weekend. We would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric C. CA $146 CA $329 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2025-11-12&endDate=2025-11-13®ionId=6047665&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Find out more about The Berkshires ### The Berkshires attractions for couples The Berkshires offer a stunning blend of natural beauty and cultural richness, making it a prime location for discerning travellers. Begin your adventure at the renowned Tanglewood, the summer home of the Boston Symphony Orchestra, where you can enjoy world-class concerts set against a picturesque backdrop. For outdoor enthusiasts, the Appalachian Trail provides breathtaking hiking opportunities, with trails that cater to various skill levels, promising memorable family outings. Art lovers will appreciate the Massachusetts Museum of Contemporary Art (MASS MoCA), a vast exhibition space showcasing innovative works in a former factory, ensuring a unique cultural experience. Families can explore the interactive exhibits at the Berkshire Museum, which engages both young and old with its blend of art, history, and science. Finally, don't miss a visit to the charming town of Stockbridge, famous for its quaint shops and the historic Norman Rockwell Museum, where you can delve into the artist's iconic works. For a comfortable stay, consider lodging in Lenox, where luxury hotels like the Miraval Berkshires Resort & Spa offer exceptional service and a wealth of amenities, including relaxing spa treatments and gourmet dining, making your exploration both convenient and indulgent. ## Top The Berkshires Hotel Reviews ![Vacation Village in the Berkshires](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Good location; reasonable price; very clean and quiet - would definitely return" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Everything is clean " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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 "Clean room" [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "This is a historical hotel and indeed the history is fabulous, everything appears like it did in 1773. Trouble is the rooms are also like this and the beds felt like they were 200 years old - so very uncomfortable. All part of the experience. Our room faced the street and I was surprised how much traffic noise kept me up until late at night, next time I will request a room facing inward. Not enough staff at the bar and dining during peak weekends, took forever just to get a cup of hot chocolate for the kids. But, very quaint, beautiful, that Main Street is just classic. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Jiminy Peak Mountain Resort](//images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830_y.jpg) ### Jiminy Peak Mountain Resort 10/10 Excellent "This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay." 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