Of course, it’s an immense privilege to be planning cottagecore and cabin retreats, or even use “weekend” as a verb in These Strange and Uncertain Times. So as we carefully plan weekend trips to nearby towns with our quar bubbles, lover(s), or fabulous selves for a one-person getaway, it's crucial to travel in accordance with the CDC’s evolving Covid-19 guidelines.
Keeping it close to home helps. Who said you have to vacay so far away, anyway? The following seven upstate towns offer top-rated experiences in art, culture, and good eats — and lodging is plentiful on sites like Airbnb, TripAdvisor, Plum Guide, and VRBO. We’ve also made a point of plucking the best accommodations — from the affordable to the hyper-luxe — to please the senses, and offer a wanderlust-worthy backdrop for a truly relaxing weekend.
What’re you waiting for? Your IRL Hallmark movie set awaits. Only, with less 2000s-era infinity scarves and more scenic views and high-powered WiFi.
At Refinery29, we’re here to help you navigate this overwhelming world of stuff. All of our picks are independently selected and curated by the editorial team. If you make a booking from a recommendation on our site, Refinery29 may earn commission.
Kingston, NY
Cobblestone streets. Tempeh Rueben sammies. Homesteading for beginners, and artisanal stores for even the pickiest shoppers. Kingston is the heritage town where city millennials love to put up their feet on the proverbial milking stool, and it’s just two-ish hours north of NYC.
What to do: Explore the Uptown Historic District as you poke into mom-n-pop shops, and pet the farm animals at Forsyth Park. Munch at concept businesses like the Outdated Café, which is a hybrid antique shop and vegetarian restaurant that could’ve rolled right out of a Nancy Meyers movie. Finally, don’t miss The Four Corners: the only intersection in the U.S. whose four corners’ buildings were built pre-Revolution.
Where to stay:
Airbnb: The Bau Guesthaus is a beautifully restored 1890s townhouse with airy, artful interiors. It sleeps up to four guests, and is smack across the street from the Old Dutch Church.
Hotel: The Church des Artistes is the dream project of a self-described “composer and artist couple who live in a large renovated church hall in the Rondout section of Kingston, and have created a unique bed and breakfast featuring stained glass windows, freshly pressed linens and comfy beautiful bedrooms.”
VRBO: Try this cozy, one-bedroom cottage nestled in the heart of Kingston’s downtown district for a romantic couples retreat.Photo: Getty Images.
Beacon, NY
As is tradition with NYC’s greener, hippie-denizen environs, Beacon is heaven for art buffs. Only, think Timothy-Leary-meets-Lee-Ufan-minimalism. At just an hour-and-a-half from NYC by car and train, it’s a great spot for a culture trip even if you only have 24 hours.
What to do: Dia:Beacon is one of the United States’ premier museums for modern and contemporary art, housed in a beautifully converted Nabisco box-printing factory. Check out more intimate shows by BAU: Beacon Artist Union, a collective of Hudson artists, and make a sip stop at Denning’s Point Distillery as you saunter around the quaint downtown shopping area.
Where To Stay:
Airbnb: This sunny, intimate cottage has a private backyard and is a 5-minute walk to Beacon’s bustling main street.
Boutique hotel: The Chrystie House Bed and Breakfast is five star-rated, “fully restored nineteenth century Federal-
style mansion with four acres of historical garden.”
VRBO: This brick Victorian manse — which sleeps up to eight guests — dates from 1867 and is perched right on the Hudson River.Photo: Johannes Schmitt-Tegge/picture alliance via Getty Images.
Saugerties, NY
Peace, quiet, and a 151-year-old lighthouse that could make Wes Anderson swoon? The village of Saugerties is often bypassed by travelers for bigger towns like Beacon or Woodstock, but holds its own amongst Upstate escapes for its nature reserves, culinary scene, and cultural treasures.
What to do: In addition to lighthouse swooning, check out the Opus 40 sculpture park, which houses the lifetime work of Bard College artist Harvey Fite, the Falling Waters Preserve along the Hudson, and the groovy Woodstock Museum. There’s a smorgasbord of tasty restos to pick from, but don’t miss Alleyway Ice Cream, whose dairy and vegan scoops have been crowned “the absolute best ice cream in New York State” by EatThis.
Where To Stay:
Airbnb: Stay in The Waterfall Cottage, a modern, cozy three-guest home 15 minutes from downtown Saugerties that backs up to an actual waterfall.
Boutique hotel: The Homestead is nestled into an 80-acre, over 200-year-old animal sanctuary. "[Rooms] feature original wide-plank floors, exposed brick walls, gorgeous fireplaces, and tasteful furnishings."
Plum Guide: Try Drifting On By, a riverfront palace with sweeping views of the Hudson River.Photo: Getty Images.
Red Hook, NY
No upstate town does pastoral romance quite like Red Hook (not to be confused with Red Hook, Brooklyn). The sleepy little town is the perfect place to watch the leaves change color in the fall, and find yourself in pin-drop silence nature about two hours away from NYC.
What to do: Visit insta-darling boutiques like Vaux Vintage, and then go for a stroll in your new linens in Poets’ Walk Park, est. 1850 as a self-declared “series of ‘outdoor rooms’ separated by stands of trees and stone walls — created for the owners of two neighboring estates.” (You can bet Washington Irving was a fan.) Once you’ve written the Next Great Novel, pull up a chair at the Historic Village Diner, a dreamy 1920s stand-alone diner.
Where to Stay:
Airbnb: Ten Neighbors is a 1970s-style house on six acres of forest, and the perfect place to house your quarantine crew. It sleeps up to eight people, and “the layout of the house is perfect for groups as there are many different areas to lounge, relax, cook, etc.”
Hotel: The Grand Duchess wears its namesake well. The Victorian B&B has retained all of its period charm, inside and out, “from the vintage formal parlors, to the privacy of your stylish and charming rooms.”
VRBO: This modern glass house was fully renovated in 2012, and sits on the banks of the trout-filled Roeliff Jansen Kill River.Photo: Getty Images.
Hudson, NY
The pull of this town is soon to be a local secret no more – hell, Vogue just proclaimed it “the Brooklyn of the Hudson Valley” – but then again, it’s always been a poster child for three staples of upstate exploring: antiques, eccentric architecture, and innovative eats. It’s a two-and-a-half hour drive from New York City, and perfect for the weekend.
What to do: Go on an architectural bender. Start with Olana State Historic Site, the whimsical 19th century home of the great Hudson River School painter, Frederic Edwin Church, then soak up the rest of the town's Queen Anne mansions (even the Hudson Library is a looker). Plop yourself on Warren streets for the top-notch boutique shopping, and bite into the latest sourdough darling bakery, Breadfolks.
Where to Stay:
Airbnb: A private, immaculately kept apartment in this historic 1865 farmhouse is the perfect place to relax, with easy access to Hudson’s restaurant-filled downtown.
Boutique hotel: The Inn at 34 is a 19th-century hotel rooted in homegrown hospitality. “The concept is really quite simple,” reads its website, “As in times past, the owners live and work at the inn. Herbs and vegetables are grown in the garden, bread and pastries baked in our ovens. Our breakfast menu is based on availability from our own garden and neighboring farmers.”
Plum Guide: Gallic Americana is a chateau-inspired apartment that sleeps up to six people. It’s walking distance from the shopping and dining district on Warren Street and feels more like an opulent Parisien pied-a-terre than an upstate New York retreat.Photo: Getty Images.
New Paltz, NY
Lest you think this unromantically-named hamlet is merely a crunchy college town, know that it’s actually a mega-historic locale that was actually settled by the Huguenots in the late 1600s (and inhabited by the Lenape Esopus tribe for centuries prior to that). It’s located in convenient proximity to a vast network of breathtaking state parks and preserves, making it a must-visit for any outdoor enthusiast.
What To Do: While the town’s main drag is dotted with excellent eateries from across the cuisine spectrum (everything from the authentic Italian fare at A Tavola to pub fare at Garvan’s), the real draw is the outdoors. From north to southwest, the Mohonk Preserve, Minnewaska State Park, Awosting Reserve, and the Shawagunk Ridge form of chain of preserved wilderness containing an indescribable expanse of nature that includes hiking and biking trails, rock climbing, swimming holes, and scenic views.
Where To Stay:
Airbnb: This cozy attic “charmer” is located in downtown New Paltz, allowing access to the hamlet’s shops and restaurants with natural attractions a short drive away.
Hotel: It’s pretty pricy, but it’s all about location — not only has the historic Mohonk Mountain House has been accommodating guests since 1869, it’s located within the Mohonk Preserve, giving you front-row access to the region’s incredible geography.
VRBO: This expansive, high-ceilinged modern home is reminiscent of an urban loft circa 1988, but offers easy proximity to Minnewaska State Park.Photo: Getty Images.
Narrowsburg, NY
Think all the action happens along the Hudson? Think again — this tiny-but-mighty hamlet is a suprisingly stylish destination that’s nestled along the Delaware River, close to the Pennsylvania border; and boasts creature comforts like boutique shopping and farm-to-table restaurant along with outdoor diversions like tubing and hiking.
What To Do: Narrowsburg’s miniature main drag is home to a variety of high-end boutiques — including Mayer Wasner, a multi-brand shop that stocks apparel from Lauren Manoogian and Raquel Allegra; the store and showroom of jeweler and sculptor Pedro Boregaard; and Madame Fortuna, an ornate treasure trove of vintage furniture and findings. (You can recharge over wood-fried pizzas at the Laundrette while taking in breathtaking river views.) Finally, make sure to return home via Route 97 — according to Escape Brooklyn, “a portion of this drive is called The Hawk’s Nest and it’s considered one of the most scenic drives in New York State.”
Where To Stay:
Airbnb: This chic tiny trailer is walking distance from the scenic Delaware River, nestled deep in the woods and along a creek for maximum peace and solitude. It also boasts a jacuzzi!
Hotel: The Lothian House is a restored Victorian estate decorated with antiques and oddities from throughout time.
Plum Guide: The Floating Farmhouse — located 9 miles from Narrowsburg proper — is a restored 1820s manor that has been featured in shelter bible Dwell. (!) It can sleep up to 10 guest and sits on the bank of an isolated swimming creek.Photo: Getty Images.
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