Title: Book the Best Hotels with TENNIS COURTS in The Berkshires in 2025 | 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 Hotels with Tennis Courts 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 Hotels with Tennis Courts Tonight [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-10-20&endDate=2025-10-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 21 - Oct 22](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-10-21&endDate=2025-10-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next 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) ## Top The Berkshires Hotels with Tennis Courts ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Villa, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/4f7ca94f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/3c0625c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG South Lee 9.0/10 Wonderful (761) "Lovely spot, great accommodations, friendly staff, and great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanne CA $163 CA $201 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 Bedroom Condo 1/2 mile from base | In-room dining](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/40940c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/662f1ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jiminy Peak Mountain Resort Hancock 8.2/10 Very good (983) "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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy CA $196 CA $219 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/8d18b6a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/057b9dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marion Slocomb Suite, Cottage](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/cd8fcdd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/175edf77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Terrace Inn Lenox 9.0/10 Wonderful (42) "Beautiful historic house in a great location. Responsive owner. Great visit!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abby CA $415 CA $463 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/18066543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/6658a41d_edited_267e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/f076ba69_edited_5004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/e43d10e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable Berkshires retreat on mtn resort, SISO Hancock 8.8/10 Excellent (6) "Kind and responsive host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Javier CA $226 CA $673 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Hancock-Hotels-Comfortable-Berkshires-Retreat-On-Mtn-Resort.h109434975.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16800/16756/ceb52ab8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/16800/16756/3cec034f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/16800/16756/3d1349c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/1000000/20000/16800/16756/f07e7b76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Simsbury Inn Simsbury Center 9.2/10 Wonderful (271) "I loved my stay there. Beautiful rooms, the hot tub was great! Breakfast was decent but there are plenty of food options around town if you want something better!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caitlin CA $405 CA $497 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Weatogue-Hotels-Simsbury-Inn.h16756.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/b33626c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/a3468c26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/d2134729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/f5baf2df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Vervana, Trademark Collection by Wyndham Bennington 8.2/10 Very good (1012) "Great location near historic downtown area, nice rooms. Overall, a very pleasant stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $154 CA $168 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/dbbfdf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Street view](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/bd69c93a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, Lakeside | Terrace/patio](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/6575d812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Woodside, Pet Friendly) | Terrace/patio](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/30d59e52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Interlaken Inn & Resort Lakeville 8.2/10 Very good (266) "The staff is courteous and accommodating especially the restaurant staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christian CA $314 CA $361 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Torrington-Hotels-Interlaken-Inn-Resort.h19679605.Hotel-Information) ![Smart TV, Netflix, streaming services](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/1d55e99a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, streaming services](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/2acfd77f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/adbcecbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/321c91e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### In town, newly remodeled studio with private balcony Shelburne Falls 10/10 Exceptional (118) "Great place. Quiet, clean and spacious - thank you so much " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $133 CA $219 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Shelburne-Falls-Hotels-In-Town.h33395567.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/c941b5c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/fce63aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/6839e531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/1d62c6d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities Dover 8.6/10 Excellent (31) "The apartment was in a great location to get to the ski lifts. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David M. CA $100 CA $397 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/West-Dover-Hotels-Ski-Inski-Out-Condo-With-Deck.h88639305.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/074ac974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/56c0072d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/1e2f9086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/b15ad723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### the suite @ barn & bike - private, bucolic, serene setting Red Hook 9.8/10 Exceptional (14) "We enjoyed our stay at this quiet, cozy property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $231 CA $356 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Red-Hook-Hotels-The-Suite-Gallatin-Farmstead-Private.h76400133.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=6047665&adults=2&property_amenities_group_explore=tennis_on_site&sort=RECOMMENDED&openPlayBack=true) ## Top The Berkshires Hotel Reviews ![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) ## Frequently asked questions ### How much do hotels with tennis courts cost in The Berkshires? > You'll pay between and per night for hotels with tennis courts in The Berkshires. Take advantage of our terrific deals and lock in your ideal match in only a few quick clicks. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### How many hotels with tennis courts are there in The Berkshires? > Pick from hotels with tennis courts in The Berkshires. Whether you want to keep your skills up or just play a few rallies with the kids, Expedia can help you find the right fit. ### Are there any family-friendly hotels with tennis courts in The Berkshires? > Absolutely, so gather your group and get busy planning that trip to The Berkshires! If Lenox is on your list of places to visit, make a booking at [Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires, an IHG Hotel](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information). This 3.5-star option is a popular family-friendly hotel with a tennis court, miniature golf and a playground. [Holiday Inn Club Vacations Oak 'n Spruce Resort](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h13232379.Hotel-Information) is another terrific choice where you can work on your game and chill out at the same time. Also in Lenox, it has a 2-star rating and amenities like a sauna and a laundry service. There are lots of things to do and see with your little travellers in Lenox. [Hancock Shaker Village](https://www.expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction) and [Berkshire Museum](https://www.expedia.ca/Berkshire-Museum-Pittsfield.d553248621532665288.Vacation-Attraction) deliver a wonderful day out. ### How can I find cheap hotels with tennis courts in The Berkshires? > Finding a cheap hotel with a tennis court is a piece of cake with Expedia. To discover your ideal stay, try out the filter tool to refine your search by amenities, budget and star rating. You can also sort your results by price so that the cheapest picks appear at the top. ### What is there to do in The Berkshires near my hotel with a tennis court? > The most important accessory for your The Berkshires getaway is an epic itinerary! [Sterling and Francine Clark Art Institute](https://www.expedia.ca/Sterling-And-Francine-Clark-Art-Institute-Williamstown.d6091835.Vacation-Attraction), [Williams College Museum of Art](https://www.expedia.ca/Williams-College-Museum-Of-Art-Williamstown.d6091837.Vacation-Attraction) and [Hopkins Observatory](https://www.expedia.ca/Hopkins-Observatory-Williamstown.d6091831.Vacation-Attraction) are among the top sights if you're visiting Williamstown. Pittsfield also lures travelers with its superb attractions, such as [Bousquet Ski Area](https://www.expedia.ca/Bousquet-Ski-Area-Pittsfield.d553248621532665283.Vacation-Attraction). Eager to explore more? 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