How to Have a Five-Star Weekend
10 vacation spots for you and your Ride or Die Besties, inspired by Elin Hilderbrand’s new novel
Summer is a time for many things: family road trips, hellish international travel, long slow afternoons at the beach with sand-dusted skin, evenings filled with the smell of smokey charcoal on the grill and cold bottles of rose sweating on a table covered with corn and watermelon, and, for me at least, lazy days tucked in with page-turning beach reads.
I just finished Our Best Intentions by Vibhuti Jain, and Sea Change by Gina Chung, both of which I loved, and now I am onto Elin Hilderbrand’s fab summer book: The Five-Star Weekend, which centers on super successful food writer Hollis Shaw, whose dashing husband, a beloved doctor, has just died tragically. To help get over the hump of grief, she decides to host a “Five-Star Weekend,” a gathering at her Nantucket house for a one friend from each chapter of her life. Each friend comes with their own baggage, and one with a terrible secret. It’s a juicy read.
The book has me thinking about my own Five-Star Weekend, who I might invite and where we might go. It would definitely be hard to choose just one person from each era of my life, but it’s an interesting exercise, walking back into the various chapters of you, and mining memories of days gone by.
And then of course, I thought about where we might go for our weekend. I don’t have a magnificent beachfront property (that I know of at least), so that’s where this post comes in. I’ve gathered a list of local-ish to NYC hotels (and a few choice Airbnbs) that would make lovely Five-Star Weekend destinations. Where would you go? I’d love to know.
Sylvan Motor Lodge
The Sylvan Motor Lodge was made for the Five-Star Weekend. It’s an impeccably restored 1950s motor lodge in Hillsdale that’s been transformed into a swanky mid-century getaway. The motel is located at the foot of Catamount Mountain and includes 10 super-stylishly renovated guest rooms, a big in-ground pool (with unicorn floaties), a main house with chef’s kitchen, living room, with an old record player for setting the mood. The best part of this is the property is all yours! Dana Bowen, the acclaimed food writer, operates the lodge as a vacation rental for groups and gives you the keys to the entire five acre property, which also includes an outdoor kitchen and grill for hanging poolside, and fire pits for campfire s’mores. If you haven’t been to Hillsdale yet, it’s a destination in itself, with lots of local artisans, food shops, restaurants, and breweries.
The North Fork
I’ve been going out to the North Fork of Long Island for about 25 years now, well before it was cool and hip. Now it’s got the top-notch wineries and restaurants, and the glam, and more traffic, but it’s still much more chill—Trader Joe’s to the Hamptons’ Whole Foods.
Twenty years since I first started heading out to Greenport in the summers, there are now many noteworthy spots to eat out: John Fraser’s North Fork Table & Inn, Claudio’s, the Little Creek Oyster Bar behind the Greenport Carousel, Dureya’s out by Orient State Park, and the fabulous fried chicken at Jennie’s pop-up at Drossos Mini Golf.
But, to tell you the truth, I have not been impressed with the hotels in the North Fork. You can do something low-key and kitchy with the Silver Sands, but if you’re looking for something more upscale, it’s not great. I stayed at the Sound View last year, and it was an overpriced disaster, and I just can’t wrap my mind around the crazy cost of most North Fork hotels. Which is why I go the Airbnb route. I have a few that I have returned to over and over, a couple that are too small for a big group, but two that would work perfectly: this one which is right on the beach in Bating Hollow that can sleep at least 10, and this one, in Mattituck, also on the beach with a ton of room for up to 10. Both have amazing hosts and are beautiful places to relax and recharge (even in winter!)
The Rockaway Hotel
I’ve written a lot about The Rockaway Hotel, I know, you’re sick of reading about it, but it’s amazing there and I love it. You will too! Located a couple of blocks from the beach, it’s got everything you want for your Five-Star Weekend: gorgeous design (it’s a very Bali meets Surfer vibe), a luxurious spa, fabulous dining (a pool bar, a rooftop lounge with sweeping views of the sea, and an American bistro with raw bar), daily Wellness Classes, community-driven programming including Artist’s Table dinner series, free swim lessons for local kids with their nonprofit partner Rising Tide Effect, a great little Supply Shop for all your beach needs (including Zingara’s vintage terry cloth designs). There are lovely sun-drenched rooms with balconies and bay/ocean views, but if you’re doing a weekend with your Five-Star besties, they have two-bedroom Bungalows too, with full kitchens, living spaces and plenty of room for your Ride or Die crew.
The Cutest Little Bungalow in Rockaway
Ok, sure, The Rockaway Hotel is the bomb, but if you’d rather stay like a local and have a place to call your own, I’m sharing the best kept secret in Rockaway: the cutest little bungalow, owned by a former Calvin Klein designer.
I love Lauren’s place and have stayed here solo and with my kids. I covet all the vintage pieces, special curated design touches, quality bedding and towels, and feel-good beach vibes. It’s the ideal spot for a weekend with your besties: two bedrooms, a chef’s kitchen, an airy open plan concept with dining room and oversized living room, a cute back yard for al fresco dining, and just a short stroll to Beach 67. During the week, you can grab day passes to the Rockaway so you get some pool time. Tell Lauren that I sent you!
Little Cat Lodge
Little Cat Lodge is a beautiful 14-room Alpine-inspired hotel and restaurant from partners Noah Bernamoff and Matt Kliegman, who own and operate award-winning restaurants and bars like The Smile, Grand Army, The Jane Hotel Ballroom & Rooftop, Celestine, Black Seed Bagels and Pebbl. Little Cat has a beautiful swimming pool and a swanky pool bar (open to hotel guests only) with lovely lounge seating and umbrellas, and poolside service on the weekends. If you want to get out into nature, there are lush forest walkways, ideal for hiking. (They’ll even pack you a boxed lunch for your adventures.) The restaurant at Little Cat Lodge includes a tavern with an Alpine-inspired menu, highlighting the lush bounty of the Hudson Valley, with a year-round terrace overlooking the majesty of Catamount Mountain.
Woodstock Way Hotel
I love the rustic modern design of this Woodstock hotel, a little oasis tucked behind the Tannery Brook Waterfall, along a babbling brook, just steps away from Woodstock’s iconic town center. Their sustainable and conscious designed space offers both gorgeous guest rooms and magnificent forest residences for your Five-Star crew. In addition to rooms, the property features The Tannery, a multi-functional communal and lobby space that is an ode to the historic tannery that once stood here in the 1800s and to the creative spirit of the 1960s. The Tannery serves drinks and snacks, serves as a gallery of original prints from iconic musical moments, and is a market for artisan wares like locally farmed jams and honey, a selection of vintage accessories, Lord Jones CBD products, to our exclusively scented Casa Posta toiletries and candles. Also, for those of you with a four-legged friend. They have rooms made for you and your puppies with treats, bones, bowls and beds!
Hotel Lilien
The Hotel Lilien looks like it fell off of a postcard: a big old Victorian, artfully restored and thoughtfully curated 18-room boutique hotel and cocktail bar in Tannersville, NY, just a stone’s throw from Hunter Mountain. The hotel comes from The Lost Boy Hospitality Group, David Harmatz, Jason Marcus, Daniel Saxe, and Daniel Smetana, a group came to be known as “The Lost Boys,” a reference to the Neverland-like experiences they craft for their guests.
Indeed, the Lilien has a magic to it: stunning views of the mountains, beautiful bedrooms and suites, a vintage billiards table, board games, and a sweet swimming pool, fireside coziness, and a restaurant and bar. It’s the perfect place to unwind with your nearest and dearest for a weekend of swimming, sunning, and drinking and eating, the right recipe to shake off the stress of the city.
If you’re heading out soon, you can make it to their July 30th Pizza Party Concert with The Wild Honey Pie and Radio Woodstock, with a special solo performance by Fruit Bats and pizza from Paulie Gee’s. Each ticket includes unlimited pizza, a free drink and live music. They’re only selling 60 tickets for this intimate experience. This event is Rain or Shine.
Scribner Lodge
This 38-room mountain lodge in the heart of the Catskills is like a smooth, modern Wes Anderson film come to life. There are 38 beautifully-outfitted guest rooms and suites, multiple indoor and outdoor event spaces, and over 20 acres of mountainside to explore. Summer is a terrific time to visit for warm weather sunning and swimming, cocktails, spa treatments galore, Wellness days, Movies on the Mountains, and more. Their locally-inspired restaurant, Prospect, leans into the boasts floor-to-ceiling windows overlooking the mountains, with a large cedar deck equipped with Westport Chairs and fire pits for the summer evening’s chill. It’s cozy and fabulous.
Inneess NY
This intimate and exquisite hotel is nestled in the base of the Catskills mountains, set on 220 acres of wild landscape with a 9-hole course designed by renowned architects and builders King Collins Golf, a pair of hardcourt tennis courts, two saltwater pools, and a full spa and gym, so you won’t have a shortage of activities. Innes is ideal for a Five- Star group gathering because offers 28 cabins and a 12-room Farmhouse, each with captivating mountain views and thoughtfully designed with custom furniture and lighting made in collaboration with Roll & Hill. The restaurant is elegant and rustic, with a menu that focuses on natural wine and the local harvest. It feels magical with a natural wood exterior, lime washed walls, vintage chairs from a Belgian church and floor to ceiling windows that offer sweeping views of the grounds and the sunset over the Catskills.
Urban Cowboy
Cool and hip, Urban Cowboy is here to show you that there is a little cowboy in all of us. Located on a secluded road in the Catskill Mountains (not too far from Frost Valley Camp if any of you are doing camp drop off!), Urban Cowboy is a fun and festive retreat that takes you to the Golden West, just burnished with a little Brooklyn attitude. Nestled on 68 acres in the heart of the Catskills, this 28-room boutique hotel offers deep soaking tubs, an outdoor restaurant with fire pits, an indoor Parlor Bar and Public House indoor restaurant (DJs play on weekends), Estonian saunas, and nature’s pool: a swimming hole. The rooms border on cowboy kitsch but it’s all good. This is a place to go and turn off your devices and just relax by the roaring fire and do nothing but get lost in the stars. Head to the nearby Menla retreat for amazing massage, yoga, and soundbaths.
Callicoon Hills
Callicoon Hills is a century-old 23-acre resort tucked in a lovely Catskills mountain valley. This charming and welcoming “Friendly Resort for Nice People” where Callicoon Hills sets you up for all the things: hiking, snow shoeing, swimming, fishing, and more. There’s also a seasonal King Sized pool, fancy patios with fire pits and adirondack chairs, covered porches with rocking chairs, a picturesque lake and burbling creek, and a lovely restaurant and bar. It’s a place you’ll also relish in doing absolutely nothing but reading a good book (The Best Intentions, Maame, and Carrie Soto is Back are some great summer reads if you need one).