Title: Book the Best ROMANTIC Hotels in Pittsfield, MA from CA $135 - Pittsfield Romantic Getaways | 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 Romantic Hotels in Pittsfield, MA from CA $135 - ![](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 Romantic Hotels Tonight [Dec 25 - Dec 26](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-12-25&endDate=2025-12-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [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&travelerType=romantic) 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&travelerType=romantic) 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&travelerType=romantic) ## Our top choices for Pittsfield 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/a25612d3.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) ![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) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) Pittsfield 8.0/10 Very good (998) "Staff was very nice and helpful nice place restaurant was awesome great food and drinks" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank CA $121 CA $135 total includes taxes & fees Jan 2 - Jan 3, 2026 [](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) ![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) ![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) ![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) ### The Yankee, Trademark Collection by Wyndham [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) Lenox 9.2/10 Wonderful (1000) "Friendly staff, very clean room and super comfy bed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda CA $127 CA $142 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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) ![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) ![Deluxe Room, Private Bathroom (Field of Dreams)](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/d973dbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbour House Inn [](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) Cheshire 9.4/10 Exceptional (53) "The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) alton CA $270 CA $286 total includes taxes & fees Jan 20 - Jan 21, 2026 [](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.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!! [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) Lanesborough 9.8/10 Exceptional (271) "What an ideal place to make home base for an extended weekend in the Berkshires with activities. Place is a gem in the woods but accessible to everything. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) liz k. CA $185 CA $286 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.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) ![Room (Firehouse)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130.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 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) Stockbridge 8.8/10 Excellent (1000) "Old time charm and hot tub under the stars" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori CA $185 CA $268 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.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) ### Berkshires Untold [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) Lenox 9.0/10 Wonderful (821) "Easiest check in and out. Great food in dining room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $173 CA $193 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.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) ![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) ![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) ### The Williams Inn [](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) Williamstown 9.6/10 Exceptional (553) "staff was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim CA $282 CA $316 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/ed652faf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Double Room, Ensuite (Early American Suite 201)](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/366b65ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/d7cd7f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/67356bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1896 House Country Inn & Motels [](https://www.expedia.ca/Williamstown-Hotels-1896-House-Country-Inn-Motels.h18670223.Hotel-Information) Williamstown 6.6/10 (448) "The price is good. It's a classic motel from the '50's, but gets the job done." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) edson [](https://www.expedia.ca/Williamstown-Hotels-1896-House-Country-Inn-Motels.h18670223.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/2788df34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/2435c38a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/a7eb284a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, stereo](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/d5a96942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bed Berkshire Apt minutes to Jiminy Peak Ski [](https://www.expedia.ca/Stephentown-Hotels-2-Bed-Berkshire-Apt-Minutes-To-Jiminy-Peak-Ski.h64428459.Hotel-Information) Stephentown 8.4/10 Very good (12) "Great location and property. thank you" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine P. CA $179 CA $356 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Stephentown-Hotels-2-Bed-Berkshire-Apt-Minutes-To-Jiminy-Peak-Ski.h64428459.Hotel-Information) ![Business centre](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Suite, Private Bathroom (RedBird Suite)](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ab46e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun 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.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) Stockbridge 9.2/10 Wonderful (110) "Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $522 CA $632 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.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=2026-01-08&endDate=2026-01-09®ionId=9478&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield Hotel Reviews ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![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 "My stay was great with no problems. " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Yes" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Hilton Garden Inn Lenox Pittsfield](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/5fa17ca2_y.jpg) ### Hilton Garden Inn Lenox Pittsfield 10/10 Excellent "The room was very clean with comfortable King bed. We really enjoyed the hot tub." [](https://expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Pittsfield? ### When is the best time of year for a romantic getaway to Pittsfield? ### What is there to do in Pittsfield? ### What's the best way to get to Pittsfield and around town during my romantic getaway? ## 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) - 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