Best Hotel Pools in Upstate New York and Connecticut

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Looking for an alternative retreat for summer 2023? Here are the best boutique hotels and inns in the Hudson Valley 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.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.

The pool at Scribner’s Lodge boasts impressive views of Hunter Mountain, located just across the street from the hotel. 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, formerly the Washington Irving Inn, recently underwent a complete facelift in 2022.

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 , 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.

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.

 

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