Title: Book the Best ROMANTIC Hotels in Lanesborough, MA from CA $137 - Lanesborough Romantic Getaways | Expedia.ca [Lanesborough Travel Guide](https://expedia.ca/Lanesborough.dx6005408)[Hotels in Lanesborough](https://expedia.ca/Lanesborough-Hotels.d6005408.Travel-Guide-Hotels)[Vacation Rentals in Lanesborough](https://expedia.ca/Lanesborough-Vacation-Rentals.d6005408.Travel-Guide-VacationRentals)[Lanesborough Car Rentals](https://expedia.ca/Car-Rentals-In-Lanesborough.d6005408.Car-Rental-Guide)[Lanesborough Vacation Packages](https://expedia.ca/Lanesborough.d6005408.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/effac09092f1740656c098e2230b5f3f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Caitlin Reese # Find Romantic Hotels in Lanesborough, MA from CA $137 ![](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 Lanesborough Romantic Hotels Tonight [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=6005408&startDate=2025-10-20&endDate=2025-10-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Oct 21 - Oct 22](https://www.expedia.ca/Hotel-Search?regionId=6005408&startDate=2025-10-21&endDate=2025-10-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6005408&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6005408&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top Lanesborough Romantic Hotels ![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 (261) "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 $189 CA $296 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.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) ![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 Williamstown 9.6/10 Exceptional (526) "Nice place to stay for a wedding " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy CA $261 CA $292 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.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) ![Front of property](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/86910798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Farm Inn Lenox 9.4/10 Exceptional (161) "Inn was gorgeous and staff exceptional!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joyce CA $226 CA $253 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.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 (107) "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 $434 CA $525 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.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) ![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) ![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) ### The Yankee, Trademark Collection by Wyndham Lenox 9.0/10 Wonderful (1015) "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 CA $178 CA $198 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.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) ![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold Lenox 9.0/10 Wonderful (769) "We had a nice room and the food was delicious. Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vincent CA $123 CA $137 total includes taxes & fees Nov 2 - Nov 3 [](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) ![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) ![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 (1014) "Picture perfect Inn" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jeff CA $188 CA $273 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/7aa060b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Deluxe King](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/ed603c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/4d651e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/65e7ad44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dewey Lenox 8.8/10 Excellent (326) "Great spot. Lots of history. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Neil CA $183 CA $205 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Lenox-Hotels-The-Dewey.h5202927.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) ![Interior](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/f4d43d3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Constance by the Lenox Collection Lenox 8.4/10 Very good (554) "Very quiet and comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth CA $158 CA $177 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Lenox-Hotels-Rookwood-Inn.h4945461.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) ![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 Pittsfield 8.0/10 Very good (914) "Enjoyable stay. Staff were very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claire CA $144 CA $161 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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=2025-11-03&endDate=2025-11-04®ionId=6005408&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Lanesborough 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 "Front desk was friendly and helpful. Plenty of parking near our specific unit. Our room was clean, spacious, and very comfortable. The pool and hot tub area were clean and had plenty of towels to use. This was our first time here and we will definitely come back. " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 "In a very nice annex suite." [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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 "Enjoyable stay. Staff were very nice. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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." [](https://expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.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.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Lanesborough? > Are you looking for a romantic vacation? While you're in Lanesborough, you'll find plenty to see and do. During your trip, you might consider a visit to Mount Greylock State Reservation Visitor Center or Mount Greylock State Reservation while you're exploring Lanesborough with your significant other. Whether you want to soak in a hot tub or watch the sunset from your balcony, you'll be sure to find accommodation in Lanesborough to make for the perfect couples' weekend. ### What's the best accommodation for a couple visiting Lanesborough? > [Berkshire Village Carriage House - Super Private!!](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) is a favorite guesthouse for couples, and features in-room kitchens and free WiFi. ### When is the best time of year for a romantic getaway to Lanesborough? > If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Lanesborough: The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Lanesborough are January, March, February, and November, with each month seeing an average of 7 inches of snowfall. ### What is there to do in Lanesborough? > There's nothing better than seeing a new destination with your sweetheart, so consider taking time to discover all that Lanesborough has to offer. You might consider a visit to Mount Greylock State Reservation Visitor Center or Mount Greylock State Reservation while you're in town. ### What's the best way to get to Lanesborough and around town during my romantic getaway? > These transportation options in Lanesborough might help your romantic getaway go off without a hitch: Make your way to Lanesborough with a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest major airport located 7.1 mi (11.5 km) from the city center. 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