Title: Book the Best ROMANTIC Hotels in Pittsfield, MA from CA $145 - 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 which includes flowers and heritage elements](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105629-Pittsfield.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Pittsfield, MA from CA $145 - ![](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 [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-04&endDate=2025-11-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-05&endDate=2025-11-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top 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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.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 (939) "Spotless and friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nikisha CA $144 CA $161 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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 (264) "This VRBO was perfect for what I needed. The property was gorgeous, the house was clean, and it had everything I needed for a nice stay. Thank you! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Britt F. CA $190 CA $295 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.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) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f43c89bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham Lenox 9.0/10 Wonderful (1030) "Great place. Friendly staff and very well located. Great breakfast options. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abiezer CA $163 CA $182 total includes taxes & fees Dec 5 - Dec 6 [](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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/ffb7a388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbour House Inn Cheshire 9.4/10 Exceptional (52) "We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lorie CA $343 CA $363 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.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) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.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) ### Berkshires Untold Lenox 9.0/10 Wonderful (789) "Easy parking, great community spaces, beautiful decor! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerry CA $130 CA $145 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.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/d969459c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Main Inn Queen)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3ac2703b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1028) "Food was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily CA $197 CA $283 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/f3e43c7f.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) ### The Williams Inn Williamstown 9.6/10 Exceptional (532) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SIDNEY CA $277 CA $309 total includes taxes & fees Nov 17 - Nov 18 [](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) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/ba469908.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) ![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) ### 1896 House Country Inn & Motels 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) ![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) ![Interior](https://images.trvl-media.com/lodging/74000000/73070000/73062200/73062141/2d6ee5bc.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 house was in great condition and the owner was super helpful. Location was amazing as it was right at bottom of ski slope." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) KC D. CA $148 CA $330 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Hancock-Hotels-Deluxe-Yeti-Suite-On-Jiminy-Mtn-1st-Flr-Sleeps-4-New-Fully-Redone-Country-Inn.h73062141.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/2e09a8f3.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) ![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) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood Stockbridge 9.2/10 Wonderful (109) "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 $429 CA $519 total includes taxes & fees Nov 16 - Nov 17 [](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=2025-11-18&endDate=2025-11-19®ionId=9478&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield 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 "The amenities are great. The pool and hot tub are very comfortable temperatures, pool tables, ping pong, foosball, arcade games, movie theater, and more." [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Hilton Garden Inn Lenox Pittsfield](//images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/5fa17ca2_y.jpg) ### Hilton Garden Inn Lenox Pittsfield 10/10 Excellent "We had a lovely stay: very comfortable beds, clean room, and pleasant staff. I particularly appreciated the ample closet and plenty of complimentary coffee pods for the Keurig. It was also wonderful to have a restaurant in-house (Jae's has amazing food!). One suggestion would be a non-slip mat for the shower: it was so new and so clean that it was a little slippery. " [](https://expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.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 "The restaurant was so delicious …the fries were the best fries I have ever had …will never forget how tasty they were !!!" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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 "The Red Lion Hotel was a great place to stay!! I would definitley come back again and stay there! I loved the bar downstairs and the restaurant! Our room was perfect and we had lots of room! The bed was super comfy - a marshmallow bed!! LOL! The location was nice to walk to the different shops in town! Fun place! " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Pittsfield? > Are you in need of a romantic escape? Our guests also enjoy Pittsfield for its theater scene and sporting events. If you want to explore the area, you might head to Berkshire Museum, Colonial Theater, or Barrington Stage Company. If you'd like to stay close to a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you and your partner will get to see everything on your list. ### When is the best time of year for a romantic getaway to Pittsfield? > If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Pittsfield: The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall. ### What is there to do in Pittsfield? > There's nothing better than seeing a new destination with your sweetheart, so consider checking out all there is to see and do in Pittsfield. Adventurous pairs will enjoy Pittsfield for its sporting events. You might think about visiting Berkshire Museum, Colonial Theater, or Barrington Stage Company. ### What's the best way to get to Pittsfield and around town during my romantic getaway? > These transportation options in Pittsfield might help your romantic trip get off to a smooth start: The closest major airport is Pittsfield, MA (PSF-Pittsfield Municipal), located 2.5 mi (4 km) from the city center. To see more of the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station. ## 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) - 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