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Poolside Terrace

Poolside Terrace

From May-Labor Day* we invite you to lounge Poolside with us! Our outdoor pool area is complete with cabanas making it the perfect summer destination. While at the Pool you can also enjoy incredible summer cocktails, dining by Fox & Hounds, and fun live music.

Planning a summer soirée? There’s no better place to host your event or poolside party than at The Cheshire! The sundeck can accommodate a variety of group sizes for numerous affairs, and our lovely outdoor pool setting is enhanced by ample seating, a poolside bar, and live musicians most weekends over the summer! You can even enjoy delicious hors d’oeuvres while lounging with your guests**. We are the destination for relaxed summer celebrations for locals and guests alike. Premium poolside rooms are available.

*Weather permitting

**For those who are not guests of The Cheshire, day pool passes are available for $30/day per person on weekdays and $50/day per person on weekends. Passes are based on occupancy and availability. In addition to pool access, the day pass will include a room key which will also allow access the Wellness Center with shower facilities. Purchase your Cheshire Pool Pass at the front desk

Rent a Poolside Cabana

  • Each cabana starts at a $500 food and beverage minimum and need to be booked in advance
  • Cabanas at our pool are designed for up to a maximum of 12 guests
  • Pool/kitchen hours are 11am-10pm

Contact Hanna Mohesky at to check availability and reserve your perfect summertime celebration!