10 Beautiful Towns to Visit in Upstate New York

Lake Placid is popular with outdoor adventurers year-round
Lake Placid is popular with outdoor adventurers year-round | © Charles O. Cecil / Alamy Stock Photo
Photo of Rachel Gould
Art & Design Editor24 September 2020

Whether you’re planning a weekend getaway or an afternoon escape from the city, New York State provides a wealth of scenic towns and villages to visit. With rich histories and booming culture surrounded by pristine countryside for walkers, hikers and explorers, there’s something for everyone in these 10 stunning locations throughout upstate New York.

Skaneateles

Located along Skaneateles Lake in Onondaga County, the village of Skaneateles exudes natural beauty all year round. From charming inns and B&Bs to its historic downtown district with unique restaurants and one-of-a-kind shops and galleries, Skaneateles is a popular place for tourists, offering something for everyone.

If you’re looking for your own retreat with all the mod and cons you could need, check out these local Airbnbs.

Skaneateles has a historic downtown district | © Hemis / Alamy Stock Photo

Cold Spring

With a spot on the National Register of Historic Places, Cold Spring in Putnam County is a popular weekend getaway for New York City residents. The village center is quaint, featuring restored 19th-century buildings and independent shops. It’s the perfect place for a quiet stroll and is home to shopping, restaurants and charming bed and breakfasts. Here, hiking, biking, boating, golfing and kayaking are also at your fingertips.

There are a whole host of idyllic little flats and guesthouses in the area, perfect for putting your feet up after a day of adventure.

Cold Spring’s Main Street is lined with restaurants and independent shops | © Len Holsborg / Alamy Stock Photo

Lake Placid

Located in Essex County in the Adirondack Mountains, the village of Lake Placid was listed in US News & World Report as one of the “6 Forgotten Vacation Spots” in North America. Surrounded by pristine natural beauty, Lake Placid is a popular destination for snow skiers, hikers and bikers. The village was founded in the 19th century, and today maintains much of its original small-town charm.

Embrace the natural beauty of your surroundings by staying at one of Lake Placid’s many secluded cabin houses.

Lake Placid is surrounded by pristine natural beauty | © Charles O. Cecil / Alamy Stock Photo

Ithaca

The city of Ithaca is a popular destination, widely known for its stunning natural beauty and thriving local culture. Dine at Ithaca’s one-of-a-kind restaurants, wander in and out of galleries, attend live-music events and explore the nearby gorges and the shores of Cayuga Lake. Home to a notable population of university students, Ithaca possesses a diverse community full of history and culture.

Head over to Airbnb and have a look at the wide variety of accommodation on offer, from apartments overlooking the stunning Cayuga Lake to peaceful guesthouses hidden by woodland.

Ithaca is a vibrant university town | © James Schwabel / Alamy Stock Photo

Sleepy Hollow

Less than an hour from Manhattan, this legendary village was made famous by Washington Irving’s celebrated tale. Having preserved much of its historical charm, Sleepy Hollow is home to several points of interest, including the Philipsburg Manor, the Old Dutch Church of Sleepy Hollow and the Sleepy Hollow Cemetery, where famed historical figures such as Andrew Carnegie, Brooke Astor and Elizabeth Arden are buried. In proximity to Tarrytown and scenic walking trails throughout the Hudson River Valley, Sleepy Hollow offers the ideal combination of nature and culture.

Why not fully immerse yourself in this historic community by finding a place to stay on Airbnb? From old-fashioned suburban houses to modern apartments, Sleepy Hollow has you covered.

Philipsburg Manor is part of Sleepy Hollow | © The Photo Works / Alamy Stock Photo

New Paltz

The town of New Paltz, located in Ulster County, lies approximately 88mi (142km) from New York City and 70mi (113km) south of Albany. Largely characterized by its student population, New Paltz is home to boutique shops and restaurants. The town offers countless outdoor activities and features several cultural and historical points of interest, including the Historic Huguenot Street and the Elting Memorial Library.

If you’re looking for a quiet retreat, then look no further. New Paltz has a ton of cute cottages, barns, cabins and secluded guesthouses to help you escape to the countryside.

New Paltz offers several historical points of interest | © Bill Gozansky / Alamy Stock Photo

Tarrytown

Located only 31mi (50km) north of New York City, Tarrytown sits on the eastern shore of the Hudson River. Steeped in local history, with original Dutch settlements dating back to the 17th century, Tarrytown is an ideal destination for New Yorkers looking to escape the city for a day. Points of interest include Lyndhurst Mansion (Jay Gould’s Gothic Revival estate), Sunnyside (the home of famed American author Washington Irving) and Castle Hotel & Spa (a 19th-century Norman-style castle on the Hudson River).

Make Tarrytown a home away from home by having a look on Airbnb and choosing any of its diverse range of homely places to stay.

Lyndhurst Mansion is one of the many historical sights in Tarrytown | © Mira / Alamy Stock Photo

Saratoga Springs

Ranked one of the top 10 places to live in New York State, Saratoga Springs is a picturesque city located north of Albany. The area was settled by English colonists in the 17th century and played an important role in the Revolutionary War. Today, Saratoga Springs is best known for horse racing but prospers culturally from the Saratoga Performing Arts Center as well as the summer residencies of the New York City Ballet and the Philadelphia Orchestra.

Set up camp right in the heart of Saratoga with Airbnb, which offers a whole range of properties in the thick of the city’s culturally rich core.

Saratoga Springs is ranked as one of the best places to live in NY | © Vespasian / Alamy Stock Photo

Woodstock

One of upstate New York’s cultural center points, Woodstock is best known for sharing a name with the legendary 1969 music festival, which took place 60mi (97km) away in Bethel, NY. Today, it remains a historical and cultural haven for visitors. A popular place of congregation for artists due to its natural beauty, the town was a leading site of the Hudson River School in the 19th century, followed by the Arts and Crafts Movement in the early 1900s. The founding of the Byrdcliffe Arts Colony further defined Woodstock’s cultural influence.

Those looking for a more private retreat should look no further. Woodstock has loads of secluded woodland properties, from romantic one-bed cabins to country guesthouses perfect for larger groups.

Woodstock has a rich cultural history | © Mira / Alamy Stock Photo

Watkins Glen

Popular thanks to its proximity to the bucolic Watkins Glen State Park, the village of Watkins Glen lies at the intersection between Seneca Lake and the Chemung River. It’s perhaps most widely known for its ties to auto racing throughout the 20th century and continues to attract tourists each year with summer festivals and outdoor activities such as hiking, camping and fishing.

Bask in glorious waterfront views with any one of Airbnb’s many lakeside properties, perfect for sunset watching after a day full of activities.

Watkins Glen is set on Seneca Lake | © Robert K. Olejniczak / Alamy Stock Photo
These recommendations were updated on September 24, 2020 to keep your travel plans fresh.