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pool at Troutbeck in Armenia NY

Where to Stay: Boutique Hotels in the Catskills with Pools

By inside + out | September 4, 2025

It’s the final stretch of summer, so let’s make it count.  If you’re planning your next adventure in the Hudson Valley, we recently shared a list of hot boutique hotels with pools to cool down in style.  Welcome to part two of that story. This time, we venture just beyond the central Hudson Valley to discover more stunning Catskills stays with luscious pools to luxuriate in. Come on in–the water’s divine.

The Amelia | Hudson NY |  @theameliahudson

pool at The Amelia in Hudson NY

This beautifully restored retreat, once a private residence in the Queen Anne style, blends the charm of a country house with a modern aesthetic, inviting you to engage your senses and find peace in its quiet luxury and attentive service. Surrounded by roses, hydrangeas, and bluebells, the pool becomes an oasis for relaxing afternoons. The decks, adorned with inviting lounge chairs and cozy coffee tables, offer ample space for everyone to soak in the beauty and tranquility of this serene escape.

The Arnold House | Livingston Manor NY | @thearnoldhouseThe pool at the Arnold House in Livingston Manor

Located 2 hours north of New York City in the western Catskills, the Arnold House is a country retreat set on 80 acres of land with custom trails and nestled into the forest of Shandelee Mountain. Staying at The Arnold is an experience more akin to staying with old friends than a traditional hotel. With sixteen guest rooms situated across four buildings on our property, the Arnold is designed to accommodate both overnight getaways and large celebrations. The Arnold House’s newest addition is its vibrant outdoor pool! Soak up the sun on a colorful floaty or enjoy a refreshing dip with friends and family. Jump in and let the good times flow.

Callicoon Hills | Callicoon NY | @callicoonhills

pool at Callicoon Hills in Callicoon NY

Callicoon Hills has everything needed to make your Catskills getaway memorable – an oversized pool (perfect for your backstroke or pool party) with poolside snacks, 23 acres of rolling woodland designed with relaxation in mind, a yoga deck, saunas, a spacious indoor gym and numerous distinctive amenities.

The DeBruce | Livingston Manor NY | @thedebruce

The DeBruce rests on a ledge overlooking the stunning Willowemoc Valley. Complete with its 12 guest rooms, an award-winning restaurant, access to hundreds of acres of private land spanning two mountains, a river and several ponds, plus a Club Room bar and a private pool, The DeBruce is designed with calm in mind throughout every detail. 

Eastwind Oliverea Valley | Big Indian NY | @eastwindhotels

pool at Eastwind Oliverea Valley in Big Indian NY

Go further into the Catskills at the all-new Eastwind Oliverea Valley. Located on a lush mountainside offering stunning sunrise and sunset views, this newly built hotel features 26 rooms and a variety of amenities. Enjoy dining at the Dandelion Restaurant & Bar, relax in Eastwind’s renowned Lushna Cabins and Suites, or unwind in the dry saunas and infrared cabin. Gather around the communal fire pit or lounge in the hammock area. Take a refreshing dip in the heated pool while soaking in the spectacular scenery of the Catskill Mountains. Surrounded by nature, this serene retreat is the perfect destination for relaxation and adventure, no matter the season. 

Kenoza Hall | Kenoza Lake NY | @kenozahall

The pool at Kenoza Hall in Kenoza Lake New York

Originally used as a summer retreat in the Catskills during the early 1900s, this 55-acre property has transformed into a year-round destination for hotels, dining, and spa services from Hemlock Spa. An outdoor heated swimming pool overlooks the main inn and is equipped with German-inspired lounge chairs for hotel guests. Next to the pool, you’ll find a hot tub and an outdoor sauna. Kenoza Lake, located just beyond the main inn, offers opportunities for canoeing and row boating during the season.

Troutbeck | Armenia NY | @troubeck.ny

pool Troutbeck in Armenia NY

A 250-acre Hudson Valley estate hotel. Home for centuries to naturalists, poets and romantics. Revived and renewed for the locavore, the creative, the curious and adventurous. All 37 guestrooms and suites include luxurious Frette linens, king-sized beds, Bluetooth-enabled Tivoli audio radios, complimentary wireless internet, and DirecTV. Indulge in a sumptuous breakfast in bed, or a selection from the House Menu. Enjoy wellness features, like movement classes, tennis, book a treatment at Wildsmith, or, of course, take a dip in the pool.

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