Best Hotel Pools in Upstate New York and Connecticut
Find respite from the hot days of summer at one of these boutique hotels and resorts, all a short drive from New York City.
The Amelia in Hudson, N.Y.
Hudson’s newest boutique hotel, located inside a Queen Anne-style home, opened summer 2021. The property is a short walk to all of the shops and restaurants on Warren Street, but The Amelia also offers plenty of reasons to stay onsite, with an English garden and outdoor fire pit. The hotel also boasts an outdoor pool, open to guests staying in one of the eight rooms.
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The Maker in Hudson, N.Y.
A few blocks over from The Amelia, The Maker Hotel — which opened last year — offers a more traditional (and bustling) hotel stay. The luxury hotel, owned by the cofounders of Fresh beauty, features several public restaurants and bars, as well as a gymnasium and juice bar. The Maker’s pool is tucked behind the property in a private courtyard, with lush landscaping that lends an atmosphere of calm respite.
Piaule in Catskill, N.Y.
Piaule is a boutique Catskills hideaway that quickly become an in-demand getaway since opening in 2021. Guests stay in private modern cabins, each featuring a glass window wall. There’s an onsite restaurant and a spa, which features the property’s centerpiece, an indoor all-year-round heated pool and mineral plunge which overlook the mountain landscape.
Inness in Accord, N.Y.
Inness offers guests expansive grounds and views of the Shawangunk and Catskill mountains. Accommodations on the property includes farmhouse rooms and private cabins, and a slate of outdoor activities, including hiking, tennis, a wading pool and golf (the nine-hole course was designed by King Collins Golf). The property also features two saltwater pools, open to guests and members, which are integrated into the sprawling landscape.
Scribner’s Lodge in Hunter, N.Y.
The pool at Scribner’s Lodge boasts impressive views of Hunter Mountain, located just across the street from the hotel. (During the warmer months, you can take a chairlift to the top of the mountain.) In past seasons, the pool has hosted live guest DJ sets on the weekends. Bonus: afterward, you can wander the property’s garden before dining at Prospect, the lodge’s restaurant helmed by chef Alex Napolitano, before settling into one of the 38 sleek guest rooms or private cabins.
Hotel Lilien in Tannersville, N.Y.
Hotel Lilien, formerly the Washington Irving Inn, recently underwent a complete facelift in 2022. The cozy 18-room property features a communal game room and cocktail lounge — and on nice days, guests can take their beverages outdoors to the pool, which was also elevated through a renovation.
Wylder Hotel Windham in Windham, N.Y.
Formerly the Thompson House Resort, the Wylder Hotel brand stepped in to reimagine the Catskills property in 2021. Guest rooms are spread out among seven lodges and a farmhouse, which houses the hotel’s onsite restaurant, Babblers. While there’s plenty to go and do in the area, in addition to the usual activities (hammocks, firepits) Wylder also offers a Pickle Ball court, wood fired saunas, and a heated pool with an extended season — it remains open except during snow season.
Glen Falls House in Round Top, N.Y.
Glen Falls House pairs the restorative power of nature with a lowkey party vibe. The hotel offers guest accommodations in three different settings: the central main house, cottages, and “hilltops,” set a little further from the action. The hotel hosts pool parties on the weekends throughout the summer with live music; most events are open to the public, held outdoors during the day and in the Tavern at night.
Callicoon Hills in Callicoon Center, N.Y.
Callicoon Hills is a rustic vacation resort that pays homage to the golden era of summer in the Catskills. Accommodations are situated across three distinct buildings, including a restored historic boarding house, pool house (as the name suggests, located next to the resort’s seasonal outdoor pool), and motel-style rooms uphill from the main property. Nearby attractions including hiking trails, world class fishing and two charming small towns — Callicoon and Livingston Manor — with restaurants and shops.
Troutbeck in Amenia, N.Y.
Troutbeck is an upscale retreat near the Berkshires on the Connecticut border. Surrounded by greenery, the hotel’s outdoor pool and grill are open seasonally to guests, with a casual menu served deckside. Nearby, Troutbeck’s main Manor house also offers a seated restaurant for breakfast, lunch, and dinner service.
Winvian Farm in Morris, Conn.
Located in Litchfield Hills, Winvian Farm offers a more whimsical retreat with choice of 18 cottages, each different and designed around a specific theme. There’s a treehouse set 35 feet off the ground, a log cabin and indoor campsite. One cottage even contains a restored helicopter, because why not? The cottages are spread out across the property’s on 113 acres, which includes a spa and organic garden that supplies Winvian’s “seed to table” fine-dining restaurant with produce. The resort’s outdoor pool is situated nearby, where guests can swim or dine on a limited lunchtime menu.
The Mayflower Inn in Washington, Conn.
In recent years, the iconic luxury hotel The Mayflower — part of the Auberge Resorts family — unveiled a redesign led by Celerie Kemble. The upscale property’s refresh also included the introduction of a new restaurant, The Garden Room. Surrounding by the idyllic Connecticut countryside, hotel guests can wander the English-style gardens or relax poolside outdoors. The spa also includes an indoor pool with views of the property’s lush landscaping visible from the French-style windows.
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