The Best Labor Day Getaways From New York City

The best escapes from NYC include the great outdoors of Vermont
The best escapes from NYC include the great outdoors of Vermont | © XKarDoc / Getty Images
Photo of Molly Codyre
24 August 2020

Labor Day is one of your last chances to enjoy a summer getaway, so it’s no wonder that everyone seems to leave New York City during this holiday weekend. The Hamptons are nice and all, but here are some alternative places you might want to check out.

The beaches of Nantucket

Nantucket has a few beaches to choose from | © Clarence Holmes Photography / Alamy Stock Photo

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  • An hour-long flight or a seven-hour drive away, Nantucket is more accessible than you might think. Lobster rolls, boat rides, biking through quaint towns – it’s the picture of New England charm. And though it’s sure to be full of people on Labor Day weekend, the crowd is relaxed and low-key.

    Fully renovated cabin on the water

    Map View
    Courtesy of Edin / Airbnb

    This cabin sits on stilts over the water in the heart of town – there’s no better location on Nantucket. Although refurbished, the house retains its historical seaside vibe, but with a modern sheen. Think a Smeg fridge, exposed wooden elements and enormous doors that you can throw open to drink in the sea air. With two bedrooms that sleep up to six guests, there is more than enough room for a family or group of friends. The terrace – which juts out over the water and overlooks the ocean – is the perfect spot for DIY sundowners before heading into town to discover the dining scene.

    Adventure in Vermont

    Vermont is a perfect escape for outdoor adventurers | © Jerry and Marcy Monkman/ / Alamy Stock Photo

    New York City is a mere four-hour drive from Manchester, Vermont, where you can spend days hiking, canoeing, fishing, golfing or playing tennis. It’s the perfect place if you’re looking for a quiet, calm escape from the bustling city.

    Farm schoolhouse with a sauna and hot tub

    Cottages, Farm
    Map View
    Courtesy of Caroline / Airbnb

    This renovated schoolhouse on a farm is all your wilderness cabin dreams rolled into one. With vaulted ceilings and enormous windows, the house is flooded with light, and you can spend your time gazing out at the views over the valleys below or soaking up the sun on the enormous terrace. However, one of the biggest drawcards is the private hot tub and sauna where you can shelter from winter weather or sit under the stars. The hosts have thought of everything – they even supply hooded robes so that you don’t have to worry about catching a chill on the stroll from the cabin to the hot tub.

    Wine tasting in the Finger Lakes

    The Finger Lakes is a great area for wine tasting | © Michael Ventura / Alamy Stock Photo

    Only four and a half hours away by car, the Finger Lakes in upstate New York is a destination for adventurous oenophiles. The area is home to countless outdoor pursuits, including spectacular hikes, canoeing and swimming spots under waterfalls. Plus, there are plenty of impressive wine-tasting options. Check out Ravines Wine Cellars or Sheldrake Point Winery for views over the lakes. Whatever you’re in the mood for, there’s plenty to keep you busy.

    Seneca House, a private cottage on Seneca Lake

    Map View
    Courtesy of Adam / Airbnb

    Light and bright, complete with sweeping lake views, this waterside cottage sleeps six people over two bedrooms and offers direct access to the water. A short drive will take you to most of the area’s incredible breweries and wineries, making it the perfect base for exploring the Finger Lakes. If you fancy just hanging around the house, you have access to a 50ft (15m) beach on the lakeshore, or you can launch kayaks and canoes from the private lakeside dock. Outside dining spaces and a grill mean you can make the most of the incredible location during mealtimes.

    Relaxation on Shelter Island

    With beautiful scenery and lovely architecture, Shelter Island is a relaxing retreat | © Jim Fiora / Alamy Stock Photo

    Shelter Island is the perfect midway spot between the South Fork of Long Island and the wine country of the North Fork. It covers roughly 12sqmi (31sqkm) in area, so spend your time exploring and admiring the Victorian architecture. Alternatively, check out vineyards, rent bikes or explore the lavender fields for a picture-perfect weekend.

    Casa Gypsea

    Map View
    Courtesy of Primael / Airbnb

    With a private cottage set around a huge pool, this island getaway feels far removed from city life. Sleeping six guests over three bedrooms – the third being a self-contained pool house – this sprawling spot has plenty of room for the whole gang. Spend your days lounging by the pool, or head out to explore the rest of Shelter Island; the house comes with three bikes so that you can be cruising the island streets with ease. A Nespresso machine in the kitchen will keep you caffeinated in the morning, and speakers mean you can pick the perfect playlist to accompany pool days.

    Escape to Bermuda

    Bermuda is only a two-hour flight from NYC | © Krzysztof Swaczyna / Alamy Stock Photo

    Though it may seem crazy to go all the way down to Bermuda for a weekend, it’s only a two-hour flight away. And if you catch an evening flight on Friday, you’ll have three full days to soak up the sun and water. This beach paradise has everything you’d expect from a tropical getaway, from scuba diving and beachfront shopping to lounging on the sand. Though this trip isn’t the most wallet-friendly, you’ll be amazed that a mere two-hour flight can land you in the tropics.

    Private beach and pool at the Cliffs of Marley

    Map View
    Courtesy of Malcolm / Airbnb

    With a large kidney-shaped pool and a private beach, this little studio offers ample opportunity to cool off from the Bermuda heat. It’s the perfect bolthole for two, complete with a romantic private terrace with jaw-dropping views of the inviting tropical waters – it makes for a memorable breakfast spot. There’s a bus stop at the bottom of the driveway, keeping you well connected to the rest of the island – although we wouldn’t blame you for spending the duration of your stay on your private beach.

    This is an updated version of an article originally written by Dana DeLaski.

    These recommendations were updated on August 24, 2020 to keep your travel plans fresh.