Poolside Party
Houses with wraparound porches, a spacious front yard, or private beach access are amongst the most desirable in Provincetown, but perhaps the most coveted real estate in town is a poolside lounge chair at the Provincetown Inn. The hotel is a sprawling ranch-style campus, with the pool at the heart of the operation. The pool is open to the public and accessible via a winding wooden path off the start of Commercial Street. During the day, you may find yourself in the middle of a bass-thumping poolside party with lounge chairs fanning out around the perimeter of the pool flanked by a bar (featuring an assortment of frozen drinks that seem nearly doctor mandated on a scorching hot day), and burgers, fry cafe and grill station. The dance hits blast from the bar and the MC isn't afraid to call you out for trying to relocate a lounge chair or any other rule-breaking poolside behavior. Despite the code of conduct, the vibe here is neighborhood block party, where everyone seems at their summer peak. With adjacent beach-side access, it can easily turn into an all-day affair.
Provincetown Inn, 1 Commercial St, Provincetown, MA 02657, (508) 487-9500
Hot Hot Heat
Access to the backyard pool at 8 Dyer will cost you at least one night stay at the hotel but there's no better way to luxuriate during your Provincetown stay. The backyard is a jungle gym of grey wood, white trim and expansive glass, reminiscent of an expensive Hampton's house, fitting for the lush boutique hotel. The pool is heated seasonally so it affords a water retreat even during the chillier months in PTown. There's also an indoor jacuzzi and sauna, both of which are complimentary for guests. It's a spa, it's a hotel and it's the easiest way to come back from vacation feeling like an entirely new person.
8 Dyer, 8 Dyer St, Provincetown, MA 02657, (508) 487-0880
Drinks on Deck
Acting as a full day-to-night one-stop-shop for Ptown fun, the Crown and Anchor houses bars and restaurants, as well as a pool on their back deck, which is open to the public and always down for a party. The pool features a slightly smaller deck and less chairs than Provincetown Inn but also boasts a burgers, dogs and fries grill and a lineup of delicious boozy frozen drinks. (If frozen isn't your thing, you can also grab a drink from inside the attached Wave Video Bar.) And because this is Provincetown, your bathing suit is your day-to-night ensemble so mingling between the pool and bars requires nothing more than a good towel, stamina and confidence.
Crown and Anchor, 247 Commercial St, Provincetown, MA 02657, (508) 487-1430
Family Friendly
If the best part of your vacation is the "escape" and "getting away from it all" element, The Seaglass Inn and Spa is the perfect option. The hotel is located on four sprawling green acres a short distance from downtown. Wooden Cape Cod reclining chairs dot the landscape, along with prominent American and rainbow flags giving the resort a stately suburban vibe that feels like a place JFK would have taken his family during one of his Cape vacations. A kidney shaped pool completes the picture and the big unencumbered land provides a perfect spot for kids or dogs to roam wild, play games or just enjoy greater air quality.
Seaglass Inn & Spa, 105 Bradford St, Provincetown, MA 02657, (508) 487-1286
Hidden in Plain Sight
The Brass Key suggests a secret society where membership is passed on between the different generations of the upper echelons of society. But while the luxury price tag of the hotel may make it exclusive to some, it's ultimately an inviting establishment and only a little bit secretly located. It's central to Provincetown, a mere minute from the Pilgrim monument, making it convenient for all and just off the main street. When you're hanging out in the courtyard that connects the Victorian buildings, cottages, spa and event space, you'll feel like you've discovered a secluded retreat. Central in the compound is the pool, which is also visible from one of the many balconies on any pool-facing room. You're welcome to carry on the myth of a secret society but the accommodating staff and friendly poolside conversations may dispel any notice of pretension.
Brass Key Guesthouse, 67 Bradford St, Provincetown, MA 02657, (508) 487-9005
Photo of the 8 Dyer pool in Provincetown.
For more on Provincetown, check out PAPERMAG.com/ptown