Title: Book the Best Hotels with TENNIS COURTS in The Berkshires in 2026 | 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://images.trvl-media.com/place/6047665/e95ad08c-cd3f-48ea-b01c-31171bbd50b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Photo courtesy of Berkshire Visitors Bureau # Find Hotels with Tennis Courts in The Berkshires, MA from CA $158 - ![](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 [Jan 7 - Jan 8](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-01-07&endDate=2026-01-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 8 - Jan 9](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-01-08&endDate=2026-01-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for The Berkshires hotels with onsite tennis court ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.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/ed360a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/226579d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) South Lee 9.0/10 Wonderful (817) "We had a great stay! Karaoke in the bar was a blast!! Great little condo!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie CA $155 CA $200 total includes taxes & fees Feb 3 - Feb 4 [](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) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/3f592f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/7f42759d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jiminy Peak Mountain Resort [](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) Hancock 8.2/10 Very good (988) "nice and clean, good customer service, but the room is smell. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Huang CA $302 CA $337 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/53ad91f9.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) ![Interior](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/6f64b785_edited_9a5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/dcf5df54_edited_d00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable Berkshires retreat on mtn resort, SISO [](https://www.expedia.ca/Hancock-Hotels-Comfortable-Berkshires-Retreat-On-Mtn-Resort.h109434975.Hotel-Information) Hancock 9.0/10 Wonderful (7) "Kind and responsive host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Javier CA $443 CA $1,009 total includes taxes & fees Jan 8 - Jan 9 [](https://www.expedia.ca/Hancock-Hotels-Comfortable-Berkshires-Retreat-On-Mtn-Resort.h109434975.Hotel-Information) ![Indoor spa tub](https://images.trvl-media.com/lodging/1000000/20000/16800/16756/66c93564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/16800/16756/c8072a57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/16800/16756/42bd0921.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) ### Simsbury Inn [](https://www.expedia.ca/Weatogue-Hotels-Simsbury-Inn.h16756.Hotel-Information) Simsbury Center 9.2/10 Wonderful (283) "The personnel was very helpful & accomodating, both at the front desk & upstairs restaurant. I appreciated that they set out two rooms as adjoining even before I asked. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara CA $343 CA $424 total includes taxes & fees Jan 8 - Jan 9 [](https://www.expedia.ca/Weatogue-Hotels-Simsbury-Inn.h16756.Hotel-Information) ![Deluxe Room, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/0d5e7c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/3bbe75f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/6cfdbbaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/1495f28f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Vervana, Trademark Collection by Wyndham [](https://www.expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information) Bennington 8.2/10 Very good (1001) "Large rooms, great staff. Will stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristyn CA $145 CA $158 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/321c91e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/9db8fbec.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) ![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) ### In town, newly remodeled studio with private balcony [](https://www.expedia.ca/Shelburne-Falls-Hotels-In-Town.h33395567.Hotel-Information) Shelburne Falls 10/10 Exceptional (119) "set up great! very clean great location, WONDERFUL" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) laurie p. CA $131 CA $215 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Shelburne-Falls-Hotels-In-Town.h33395567.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/fce63aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/ef38effc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/b7233da7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/6ae09456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities [](https://www.expedia.ca/West-Dover-Hotels-Ski-Inski-Out-Condo-With-Deck.h88639305.Hotel-Information) Dover 8.8/10 Excellent (32) "Very nice accommodations and location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael M. CA $140 CA $531 total includes taxes & fees Feb 1 - Feb 2 [](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) ![Exterior](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/b15ad723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/4e24f0c1.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/dffbf68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### the suite @ barn & bike - private, bucolic, serene setting [](https://www.expedia.ca/Red-Hook-Hotels-The-Suite-Gallatin-Farmstead-Private.h76400133.Hotel-Information) 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 $205 CA $261 total includes taxes & fees Jan 8 - Jan 9 [](https://www.expedia.ca/Red-Hook-Hotels-The-Suite-Gallatin-Farmstead-Private.h76400133.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/04000126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/5200a28c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/dec25c2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/ed219351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den [](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-Den.h36778065.Hotel-Information) Dover 9.2/10 Wonderful (18) "So cute and in such a great area! It was a perfect stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaden F. CA $66 CA $411 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-Den.h36778065.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/4501ee4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/bdac3cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/3902b9c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/w1170h1596x0y468-0a8fb230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table. [](https://www.expedia.ca/West-Dover-Hotels-Fantastic-Location-Mt-Snow-Ski-Off.h101085488.Hotel-Information) Dover 9.8/10 Exceptional (6) "We enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $321 CA $799 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/West-Dover-Hotels-Fantastic-Location-Mt-Snow-Ski-Off.h101085488.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=2026-01-21&endDate=2026-01-22®ionId=6047665&adults=2&property_amenities_group_explore=tennis_on_site&sort=RECOMMENDED&openPlayBack=true) ## Top The Berkshires Hotel Reviews ## Frequently asked questions ### How much do hotels with tennis courts cost in The Berkshires? ### How many hotels with tennis courts are there in The Berkshires? ### Are there any family-friendly hotels with tennis courts in The Berkshires? ### How can I find cheap hotels with tennis courts in The Berkshires? ### What is there to do in The Berkshires near my hotel with a tennis court? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in Otis ](https://www.expedia.ca/3Star-Otis-Hotels.s30-0-d6005412.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Hotel-With-Early-Check-In.0-0-d223-thotelwithearlycheckin.Hotel-Filter-Destinations) - 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