The 16 Most Charming Small Towns in New York

Skaneateles is one of those towns that feels like it’s straight out of a movie: There’s loveliness at every turn, with lots of historic and perfectly preserved detail. Plus, every shop, restaurant and viewpoint you stumble upon will be better than the next. Speaking of the view, our favorite place to sit and gaze out over the glittering lake of the same name is the waterfront Clift Park, with its adorable gazebo, and neighboring Skaneateles Pier. Once you’ve tired yourself out exploring the dense downtown, enjoy a wood-fired, artisanal pizza at Gilda’s, a favorite amongst visitors and locals alike that offers pick-up and outdoor seating.

Where to stay:

• Skaneateles Lakefront Getaway (6 guests): $315/night
• Perfect Lakeside Getaway (9 guests): $286/night
  
• Beautifully Renovated Cottage on Otisco Lake (4 guests): $135/night

This small city (about 6,400 people) is only a two-hour drive from Manhattan and a popular getaway, thanks in part to its mid-century antique shops and lively contemporary art scene. On Warren Street, Hudson’s main drag, is Grazin’, an old-school diner with yummy burgers and cool vibes. Also on Warren is Swoon Kitchenbar, an upscale brasserie with an impressive wine list and delicious cocktails.

Where to stay: 

• Hudson Valley Getaway Cottage (5 guests): $205/night
• Renovated Apartment In The Heart Of Hudson (4 guests): $200/night
• Charming Two Bedroom Ranch House (4 guests): $250/night

You can make the 90-minute drive to New Paltz just to stay at the Mohonk Mountain House…we won’t judge. The all-inclusive Victorian-era hotel sits on 40,000 acres on the Shawangunk Ridge and looks like a castle. The sumptuous accommodation offers dozens of fun outdoor activities. New Paltz itself, now a college town, is one of the oldest towns in the U.S. with buildings dating back to the early 1700s. And, its age is a big part of its allure.

Where to stay:

• Modern New Paltz Farmhouse (8 guests): $750/night
• Private Getaway with Amazing Mountain Views (3 guests): $162/night
• Cozy and Charming Farm House (6 guests): $204/night

There are few things more pleasurable than taking a safe, socially distanced bike tour through this charming village and its main drag filled with historic buildings that line the eastern shore of Cayuga Lake. Mornings in Aurora are well spent taking in a coffee and the peaceful reflection of the lake, while days are best filled with local pottery or painting classes or at wine tastings at one of the many stops on the Cayuga Lake Wine Trail. Keep your tummy happy come the evening by enjoying an outdoor meal at a restaurant with innovative cuisine and cocktails like 1833 Kitchen & Bar or getting takeout from Fargo Bar & Grill.

Where to stay:

• Sweetgrass Cottage (6 guests): $190/night
• Unique Finger Lakes Home On Cayuga Wine Trail (4 guests): $119/night
• Rustic Log Cabin Retreat (6 guests): $179/night

Saugerties is a quintessential Hudson Valley town. The village, on the west bank of the river at the mouth of the Esopus Creek, is a historic landmark with a main street full of buildings—antique stores, restaurants, mom-and-pop shops—preserved as their 19th-century selves. Spend the day at Opus 40, a sprawling outdoor sculpture park (currently open with some COVID-19 restrictions in place; guests musts bring a mask) or bring a bike to explore one of the many gorgeous bike trails.

Where to stay:

• Brick Cottage Retreat (6 guests): $288/night
• Creekside Cottage On The Water (4 guests): $195/night
  
• Woodsy Country Cottage (4 guests): $175/night

If you blink twice, you might miss this Sullivan County hamlet on the banks of the Delaware River. But that would be a shame, because its charming Main Street is packed with cool shops, like Maison Bergogne. The outdoor activities aren’t bad either: You can canoe or kayak down the Delaware or take a relaxing float from Skinner’s Falls with Lander’s River Trips. For lunch, order takeout from The Heron (and be sure to try the fried chicken). For dinner, The Laundrette serves up delicious wood-fired pizzas.

Where to stay:

• Luxurious Lakefront House (6 guests): $213/night
• Narrowsburg Home in the Woods (4 guests): $293/night
• Modern Retreat in the Woods (6 guests): $319/night

You’ll feel completely transported in time in Cold Spring thanks to its 200-some preserved 19th-century buildings on the National Register of Historic Places. Visitors also make the trek to hike the surrounding Hudson Highlands. From the top of Breakneck Ridge, a challenging 3.7-mile loop, you’ll have some of the best views of the Hudson Valley.

Where to stay: 

• Historic Cold Spring Village House (7 guests): $295/night
• Charming Cottage in Bucolic Country Setting (8 guests): $468/night
• Beautiful Modernist Home (6 guests): $240/night

Rhinebeck gets a lot of love from travelers, and even boasts Presidential ties (former first-daughter Chelsea Clinton tied the knot here). Its popularity is deserved as the home to arguably many of the Hudson Valley’s finest restaurants, home décor, and antique shops and even a charming bookstore to discover your next great read. For $100 per person, you can fly in an old-timey 1929 New Standard D-25 at the Old Rhinebeck Aerodome, just outside of town, if you’re feeling adventurous and make a reservation ahead of time. Or plan a visit to Ferncliff Forest to climb “the tower” any time of the year; you can also mountain or fat bike here, camp, or just meditate in nature … whatever your outdoorsy heart desires.

Where to stay:

• Rhinebeck Village Suite (4 guest): $286/night
• Quiet and Peaceful Cape Cod (8 guests): $441/night
• Secluded Luxury Home (8 guests): $480/night

Forget Napa: New Yorkers looking for a quick wine getaway should look no further than Long Island’s North Fork. The antithesis of its sibling on the south shore, the North Fork is more about wineries, farm stands, sailing and country roads than about the glitz and glam of the Hamptons. Greenport is its seaside center.

Where to stay:

• Quaint Downtown Greenport Apt (2 guests): $229/night
• Renovated Family Home (4 guests): $139/night
• Beach Apartment in Greenport Village (5 guests): $386/night

This Hudson River village in Westchester is just a one-hour drive from the city, but will transport you to a completely different world (think: a beautiful arch bridge passing over a dam with gentle flowing water). At the popular Croton Gorge Park, outdoor exploration across 97 acres is a highlight, especially if there’s snow on the ground and you can cross-country ski. Though there’s less of a downtown in Croton-on-Hudson than some of the other spots featured on this list, this charmer still features hip eateries like Croton Tapsmith, a taproom offering cold brews from nearby Hudson Valley producers and locally sourced food options, as well as Ocean House Oyster Bar & Grill. And don’t miss Van Cortlandt Manor, the 18th-century stone house and brick ferry house of New York’s famous Van Cortlandt family.

Where to stay:

• Cozy Cottage Get Away (2 guests): $85/night
• Holiday Cozy Country Cottage (7 guests): $369/night
• Perfect Studio Getaway (4 guests): $161/night

Seeing the dreamy Sonnenberg Gardens and Mansion in the flesh would be reason enough to make the drive to this town, which sits on one of the sleepier and decidedly posh-er of the Finger Lakes. The popular attraction is the former summer house of a wealthy New York City family with a Queen Anne-style mansion and nine, distinct formal gardens (our faves being the Japanese and Italian gardens). It is currently open until October 31. Other popular things to do: Taking a pontoon boat out on the lake, which visitors can rent for the day from Sutter’s Marina and drive themselves as long as they are 21+ and have a valid driver’s license. And while most New Yorkers wouldn’t think of driving upstate for authentic Mexican grub, you should not pass go without trying Rio Tomatlan while here.

Where to stay:

• Canandaigua Lakefront Retreat (4 guests): $195/night
  
• Paradise on Canandaigua Lake (11 guests): $454/night
• Charming Lake View Home w/ Easy Lake Access (8 guests): $205/night

Drive just ten miles west of Saugerties and you’ll find Woodstock. (Both towns are about a two-hour drive from Manhattan and can easily be done in the same weekend.) The town may be best known for lending its name to the iconic music fest—which, fun fact, actually took place 60 miles away in Bethel—but it’s also home to a thriving art scene and has great hiking options nearby, like picturesque Kaaterskill Falls.

Where to stay:

• Wydeclove Artist Retreat (2 guests): $250/night
• Romantic Luxury Chalet for Two (2 guests): $282/night
• Streamside Cottage (4 guests): $216/night

Whether you love or loathe the Hamptons, one thing most New Yorkers can agree on is that the towns “Out East” including East Hampton, Southampton, and Amagansett are undoubtedly attractive. Still, the clear winner in our hearts is Sag Harbor, both for its adorable Main Street, but also for it’s more laid-back vibes and waterfront marinas, which you’re likely to spot as you take a stroll through the picturesque downtown. The popular Sag Harbor Whaling & Historical museum, housed in a meticulously-preserved mansion, celebrates the town’s whaling past and is open seasonally, but you can also visit it virtually for free anytime. Also on your Sag hit list, especially if shopping’s your thing: Loveshackfancy, a luxury lifestyle store and Jayson Home, a celebrated home décor shop.

Where to stay:

• Whaling Captain Pierson's Cottage (3 guests): $315/night
• Luxury Sag Harbor Village Cottage (2 guests): $325/night
• The Cooper-Burke House (4 guests): $410/night

Kingston, one of the Hudson Valley’s most popular and evolving towns that was the original capital of New York state, overflows with shopping sites sitting on not one, but two separate, picturesque main downtown streets. The artist enclave is a place you’ll find record and music stores, tattoo parlors, bookstores, and Outdated, a coffee-meets-antique shop housed under the same roof. Architecture buffs will want to take a stroll through uptown Kingston’s Stockade district to see historical old stone houses, specifically at the picture-worthy four corners—the only intersection in the U.S. where these 18th century homes sit on all four corners. Characteristic of the neighborhood, visitors will also stumble upon charming streetlights and weathered blue stone sidewalks.

Where to stay:

• Windham Mountain Family Cottage (9 guests): $375/night
• Creekside Cottage On The Water (4 guests): $195/night
• Historic Kingston 1800s Waterfront Townhouse (5 guests): $214/night