Best East Coast Winter Vacation Destinations for the Perfect Getaway

Posted on July 24, 2022 | Julie J. |

Last Updated on November 25, 2024

If you are planning your next East Coast winter vacation and are wondering where to go, discover some of the best destinations in the eastern USA to visit during winter. From weekend getaways to charming towns that turn magical during the holidays to sunny vacation spots to escape the cold, you will find the perfect place for you and your group.

Whether you want to ski, do a road trip, or spend time at the beach, whether you are looking for romantic winter destinations for couples, or planning a kid-friendly winter vacation for the family, this list of the best winter destinations on the East Coast covers it all!

HELPFUL WEBSITES TO HELP YOU PLAN YOUR TRIP

FLIGHT DEALS

HOTEL DEALS

CAR RENTAL

TRAVEL INSURANCE

ACTIVITIES

VACATION RENTALS

HELPFUL WEBSITES TO HELP YOU PLAN YOUR TRIP

FLIGHT DEALS

HOTEL DEALS

CAR RENTAL

TRAVEL INSURANCE

ACTIVITIES

VACATION RENTALS

Disclaimer: This post contains affiliate links, which means that if you click on any links and make a purchase, we’ll get a small commission, at no cost to you.

Table of Contents show

Top Winter Getaways on the East Coast

New York City

By Kelly from Travel New York Now

Looking for one of the best winter destinations on the East Coast of the USA? If so, then look no further than New York City.

After all, this iconic winter metropolis turns into a veritable winter wonderland once the temperature drops and the snow starts to fall.

So, be sure to check out iconic holiday markets at Grand Central Terminal, Herald Square, and Columbus Circle before enjoying a bit of ice skating at Bryant Park and Brookfield Plaza.

You can also shop til you drop among some of the vendors at the winter village in Bryant Park before trying your hand at curling here too.

And when you want to warm up, head to Serra by Birreria rooftop bar and relax with a mulled wine as you take in impressive, winter-themed decor that makes you feel as though you’re in a cozy ski chalet in the alps.

You can also visit the Rockefeller Center Christmas Tree before admiring the stunning annual holiday window at Saks Fifth Avenue.

Whatever you do though, be sure to try one of the most unusual things to do in NYC and take a trip to Rolf’s. It’s a fun, local German restaurant with over-the-top Christmas decor that starts getting put up around May every year. Just skip the food and order a decadent holiday-themed cocktail so you can soak up the ambiance here.

You can also get some amazing chocolate babka from the Breads Bakery kiosk in Bryant Park before settling in for a warm evening inside the Hyatt Grand Central New York – perfect for families and couples alike.

See more hotels in New York>>

See apartment rentals>>

Boston, Massachusetts

By Krystianna from Volumes & Voyages

One of the best destinations for winter on the east coast is Boston, Massachusetts! So many travelers gloss over this historic city, but it’s truly one worth visiting, as it’s filled with amazing food, fun tours, Instagram spots, and tons of fun things to do.

Plus, winter is the perfect time to visit because most of the college kids are home and most tourists opt to visit in summer, which means a much more “local” experience for you.

In the winter, some of the best things to do include exploring Quincy Market, shopping on Newbury Street, and seeing a Boston Bruins or Celtics game. Boston is a major sports city, and one of the greatest and most immersive ways to experience the city’s sports culture is by attending a game.

To get around the city easily, be sure to pick up a Charlie Card at a local supermarket or get a multiple-day pass. Truthfully, it’s near impossible to have a car in Boston – most people who live in the city don’t even have one because it’s not a car-friendly place. Instead, rely on the T and the bus to get around safely and efficiently!

When it comes to places to stay, the best place hands-down is the Fenway neighborhood. There are a few hotels in this area, but The Verb Hotel is a great option. It’s around the corner from Fenway Park and the Fenway T stop, making it super easy to get around.

Plus, the Fenway area is filled with tons of great restaurants, bars, and nightlife! Some great restaurants in the area include PLANTPUB and Honeygrow.

See more hotels in Boston >>

See apartment rentals >>

Helen, Georgia

By Jillian Michelle from Adventure Dragon

One of the best winter getaways on the East Coast is a tiny, riverside town nestled against the mountains in northern Georgia. Helen is known for its pretty, fairytale-like architecture, and this unique charm has turned the tiny town into a popular tourist destination.

During winter, every building is decorated with twinkling lights for the holidays, making Christmas in Helen Georgia the most popular time to visit of all.

The start of the winter holiday season is marked by the Lighting of the Village, a free event in which Santa Claus and Mrs. Claus arrive on Black Friday every year to turn on Christmas lights in the town’s main square.

On the very next day, the annual German Christkindlmarkt opens for tourists to shop for candy, gifts, festive food, and decor.

Helen also has an annual Christmas parade that you won’t want to miss. It’s usually held on the second Saturday of December, and kids even have the chance to hang out with Santa during a bonfire that’s held after the parade ends.

When you get hungry, stop by the riverfront Troll Tavern to eat authentic German food while sitting on a patio overlooking the water and surrounded by Christmas lights.

You also can’t forget to visit one of the town’s most photographed locations: the Helen Windmill. During winter, it’s decorated for the holidays, and you can even choose to stay the night here, at the Heidi Motel, inside one of their windmill suites.

Burlington, Vermont

By Mel from BRB Travel Blog

Burlington is a classic New England small-town which makes it the perfect postcard winter destination. Be seduced by the old colonial buildings with red bricks and cobblestones streets and the views of Champlain Lake.

The city has a vibe of a college town mixed with a local feeling led by the local food and drink scene. The main streets are filled with very diverse and eclectic stores, you can go from fancy fashion boutiques to thrift stores, old vinyl, outdoor sports, and made-in Vermont products with some hippie-style stores scattered throughout.

Don’t forget to be vigilant and look up the murals and graffiti the city has scattered around.

Burlington is a great starting point for your winter Vermont adventure since some of the best ski and winter resorts are only 1 hour away. Vermont has 20 alpine ski resorts. The most well-known mountains are Sugarbush, Smuggler’s Notch, Mad River Glen, and Stowe. In these mountains and in the state parks, you can snowshoe and snowmobile if skiing is not your cup of tea.

Where to eat and drink in Burlington Vermont? Hen of the Wood is a sophisticated yet simple farm-to-table dining. Their menu changes constantly with seasons along with their chef’s inspiration.

Ben & Jerry’s has their flagship counter since the famous ice cream parlor was created in the city.

Vermont has the most breweries & brewpubs per capita in the US as it has more than 50 breweries and 16 micro-distilleries and numerous cider houses & wineries. So why not head to a bar and taste their local selection or take a brew tour?

Where to stay? Hotel Vermont is a hip boutique hotel located in the heart of downtown and is ideal for couples and families alike.

Washington D.C.

By Julie from Fun in Fairfax VA

A wonderful collection of free indoor and outdoor activities makes Washington DC an ideal destination for a winter visit on the East Coast.

You may not encounter snow in the nation’s capital, though there are usually one or two good snowstorms every year.

Kick off the season with a December visit to enjoy fun and unique holiday activities in Washington DC. The city sparkles with special decorations and events including the White House and Capitol Christmas Trees, a huge model train display at the U.S. Botanical Garden, and outdoor shopping at the Downtown DC Holiday Market.

Stay at the Kimpton Hotel George, close to the Capitol Building and Union Station, and you’ll be near all the action.

Winter fun continues after the holidays too. An outdoor ice rink takes over the National Sculpture Garden along with a seasonal rink by the Potomac River. If you’re lucky enough to visit during snow, join a fun and friendly snowball fight organized by the DC Snowball Fight Association (find them on Twitter) or go sledding on Capitol Hill.

When it’s time to warm up, there are 16 free Smithsonian museums and galleries to choose from. Visitors can explore the history of aviation at the National Air and Space Museum, visit the dinosaurs at the National Museum of History, and so much more.

Most of the Smithsonian museums are close to the National Mall and several have nice cafeterias where you can warm up with a meal. Of course, there are plenty of great DC restaurants to sample, from fast casual spots like Fruitive to fine dining favorites like Elizabeth’s Gone Raw.

See more hotels in DC >>

See apartment rentals >>

Charleston, South Carolina

By Sam Opp from Find Love and Travel

With warm temperatures, charming streets, and tons of history, Charleston, South Carolina is a great place to visit during the winter. The winter is known as one of Charleston’s shoulder season times, so you will also be able to enjoy the city with fewer crowds!

Some of the best things to add to your Charleston itinerary include touring around Downtown Charleston to see the historic homes, cobblestone streets, and churches. The city is named the Holy City for a reason.

Some of the most beautiful homes can be found along the Battery which used to be a seawall that protected the city from invaders. These homes have all the classic southern charm and those giant Charlestonian piazza porches. Make sure to take a quick stroll down the hidden Stolls ally!

Other top sites not to miss are the famous Pineapple Fountain which is located right by the water, City Market, and a trip down King Street to shop and eat.

When looking for a lovely place to stay in Charleston, check out the Harbourview Inn. This boutique hotel is one of the only hotels located on the water.

For a great restaurant for food and drinks check out a local favorite, Husk. Their constantly changing menu incorporates locally sourced ingredients for southern dishes that highlight Charleston.

See more hotels in Charleston >>

See apartment rentals >>

White Mountains, New Hampshire

Family skiing in New Hampshire — Photo courtesy of the New Hampshire Division of Travel & Tourism

By Kate from New Hampshire Way

New Hampshire often lives in the shadow of Vermont when it comes to East Coast winter getaways — until you spend time in the White Mountains, that is. With quirky small towns, winter sports galore, endless snow-dusted landscapes, and cozy bed and breakfasts, the White Mountains are where winter dreams come true!

In Lincoln NH, spend the morning snowshoeing in Franconia Notch State Park before hitting up Gypsy Cafe for a tofu cashew stir-fry. The nearby town of Woodstock is home to Ice Castles, a complex of ice sculptures and slides that are equally gorgeous by day or night.

Littleton is another town worth exploring, with a walkable downtown that feels plucked from an earlier era, Chutter’s Candy Shop with the longest candy counter in the world, and Schilling Beer Company, the best brewery in the state with a collection of European-style brews.

Most popular of all is picture-perfect North Conway, where you can take the Conway Scenic Railroad through a winter wonderland, take a snow coach up Mount Washington, or shop till you drop at the outlets. And that’s before you hit up Cranmore Mountain for skiing!

The Franconia area is one of the loveliest places to stay in the White Mountains in the area. It feels wonderfully rural but you’re close to the highway.

If you’re looking to splurge, the Sugar Hill Inn in Sugar Hill is one of the best bed and breakfasts in the Granite State, with well-appointed rooms and an award-winning restaurant.

A value-for-money option is Kinsman Lodge Bed and Breakfast, where rooms are cheerful and proprietor Sue prepares you a delicious breakfast each morning.

Warm Winter Vacation Destinations on the East Coast

Orlando, Florida

By Shannon of Adventuring With Shannon

Orlando, Florida is one of the best winter vacation spots on the East coast for anyone who enjoys warm weather and theme parks. While other destinations around the United States are stuck inside due to blizzards or freezing cold weather, Orlando is sunny and warm year round which makes it the perfect place for a vacation to escape the winter blues.

While Disney World is the most famous thing to do in Orlando, there are many other attractions to enjoy on your vacation. If you are a Harry Potter fan, you can visit Universal Studios and experience Dragon Alley, Gringotts, Hogwarts castle, and Hogsmeade.

If you enjoy spending time in the water, you can visit waterparks like Aquatica and Volcano Bay or make your way over to Daytona Beach for an afternoon. Despite Orlando being famous for its entertainment for children, there are many things to do in Orlando for adults as well.

There are a variety of different themed restaurants all over Orlando. If you want to stay in the Disney area, Disney Springs has many options to choose from. If you are looking for a more upscale dining experience, you can head over to Winter Park near downtown Orlando for a quieter setting. If you have children and are interested in uniquely-themed restaurants, there are many on I-Drive and Icon Park to choose from.

During the winter months, the Gaylord Palms in Orlando turns into a winter wonderland that features an ice sculpture competition and a winter chorus show in the evenings. This winter transformation makes it both a beautiful place to visit and an awesome place to stay while on your vacation.

See more hotels in Orlando >>

See apartment rentals >>

Key West, Florida

By Charles from US Gulf Coast Travel

When looking for a warm winter destination on the US East Coast, you will not find better weather than in Key West, Florida. Key West is the southernmost spot along the US East Coast, has a Caribbean climate, and is only 90 miles from Cuba.

In January in Key West, the average daily high temperature is 74º and the daily low average is 66º. Put away your socks and sweaters during your visit!

The ocean water temperature near Key West is over 71º in January and water activities like snorkeling and sailing are popular.

Some fun things to do in Key West on land include visiting the Southernmost Point (the iconic red, yellow, and black buoy), The Hemingway Home (make sure to see the six-toed cats), Key West Butterfly and Nature Conservancy, the sunset celebration at Mallory Square, and much more.

But even driving to Key West is a winter treat. Key West is 159 miles from Miami Airport and 105 miles off the Florida peninsula. You will drive over dozens of bridges and islands (keys) to reach Key West and there are hundreds of places to stop and savor sun, sand, and warm water settings.

A great place to try key lime pie is Moondog Cafe.

The Marquesa Hotel is a great place to stay in Key West. This adults-only hotel with 3 outdoor pools and a nice garden is perfect for couples planning a romantic winter getaway. If you are traveling with kids, you can rent a condo near the beach.

Clearwater, Florida

By Terri from Female Solo Trek

Fiery sunsets await visitors to Clearwater, Florida. It’s the crowning glory of every perfect beach day, according to the St. Pete Clearwater Travel Bureau. Nestled on the Gulf of Mexico, Clearwater is a Caribbean-style winter getaway where you don’t need a passport.

It will appeal to visitors on a budget if you rent an Airbnb or Vrbo. Hotel rates are high during the winter. If you want to splurge, check out the beach-front Hyatt Regency Clearwater Beach Resort & Spa.

Temperatures hover between 66 and 72 degrees during the winter months. The closest airport is Tampa Bay International Airport, 22 miles away.

This West Florida city offers sugar white beaches, waterfront parks, and a walkable downtown. Come discover why USA Today named it a Top 10 Beach in the USA. Get up at dawn to watch the birds flying south from your bridge perch.

A typical vacation day includes breakfast on the hotel patio, a morning beach walk, a grouper sandwich at Frenchy’s Rockaway Grill, and afternoon suntanning.

Happy Hour starts with a piña colada at Bar Tiki Clearwater Beach. Then finish the evening at Pier 60 (Clearwater’s Main Street) to watch the sunset, drink a cocktail, shop at local crafters’ booths, and listen to music. At the marina, you can book a dinner cruise with Yacht Starship.

Nearby St. Pete and Tampa offer city escapes for foodies to enjoy great restaurants, plus street art, museums, and riverside walks.

For a nature adventure, head to the nearby island (Sand Key) or Caladesi Island State Park to go shelling, swimming, and biking.

Fort Myers, Florida

By Candice from CS Ginger

One of the best winter destinations on the East Coast is Fort Myers, Florida. There are so many fun things to do in Fort Myers like spending time at the beach, looking for wildlife, going on a sunset sail, and other outdoor activities.

Lovers Key State Park is one of the best places to spend time in the outdoors in Fort Myers. This state park is a great place to go kayaking as well as spending time at the beach. There is a 5-mile paddling trail that goes through the mangroves there. Keep an eye out for manatees and alligators. Winter is the best time to see the manatees in Florida.

The Fort Myers Beach area is a fun place to spend some time. The Fort Myers Fishing Pier is beautiful at sunset and is a great place to look for dolphins if you aren’t going out on a dolphin tour. Times Square and Crescent Beach Family Park are right next to the pier and are great places to grab a bite to eat and hang out.

Wyndham Garden Fort Myers is a great place to stay near Fort Myers Beach. It has beautiful access to the beach and is close to the main attractions in the beach area.

Miami, Florida

By Eden from Rock a Little Travel

Miami is one of the best winter destinations on the East Coast. With winter temperatures ranging from the mid-60s to the mid-70s, you’re almost guaranteed comfortable weather when exploring this lively and colorful city.

During your winter visit to Miami, be sure not to miss spending a day at the beach, enjoying a walk around the Art Deco District, visiting the Versace Mansion, viewing street art at the Wynwood Walls, and joining a guided food tour in Little Havana.

If you’re an early riser, make the effort at least once during your trip to get up for sunrise. Early morning is the best time to get photos in Miami before the crowds arrive, and you can’t beat those golden Miami Beach sunrises.

When booking your hotel accommodations in Miami try to stay in or near Miami Beach. The Miami Beach Edition and the Marriott Stanton South Beach are both great options.

For dinner and drinks in the evenings, South Beach is the place to be. Start at Planta South Beach for a healthy and delicious dinner. Afterward, make your way over to Swizzle Rum Bar & Drinkery to sip fruity cocktails in a speakeasy-like atmosphere.

East Coast Winter Road Trip Ideas

Winter Road Trip in Vermont

By Paula from Paula Pins the Planet

Taking a winter road trip in Vermont is one of the best East Coast destinations during the coldest season. Located in New England, Vermont is known for its breathtaking scenery, ski slopes, and of course, the famous covered bridges!

Visiting Vermont in the winter months is a great option for winter sports and other snow activities including skiing, snowshoeing, and snowmobiling. You can also head out on some winter hikes to enjoy the scenery.

The best way to explore the state is by heading out on a road trip, this way you can cover much more ground. For the ultimate winter vacation in Vermont, you’ll want to visit a number of places including Mad River Valley, Burlington, Montpellier, Stowe, and Woodstock.

These places are great for foodies as you’ll get to go on a Ben & Jerry’s tour, try America’s famous grilled cheese sandwiches, and visit plenty of markets. Don’t forget the local breweries or maple farms either!

You’ll also get to visit the amazing ski lodges in Stowe or rent a cabin in the mountains, and one of the best places to stay in Stowe, especially if you love winter sports is the well-known Trapp Family Lodge.

Whether you’re traveling on your own, as a couple, or with your family – Vermont has something for everyone at this time of year.

Skyline Drive, Shenandoah National Park, Virginia

Shenandoah National Park and the Blue Ridge Mountains are just gorgeous during winter – enjoy the dramatic landscape, stop at scenic overlooks, and take part in some fun winter activities.

The 105-mile road trip goes from Front Royal or Rockfish Gap. The road winds through the Shenandoah Valley to the west and the Piedmont to the east. Be aware that the road might close unexpectedly in case of severe weather.

In the area, you will find many trails open for skiing, snowshoeing, and even hiking.

Along Skyline Drive, you will find the Stony Man Trail (1.6 miles round trip), Frazier Discovery Trail (a 1.3-mile loop), and Dark Hollow Falls (a steep but short 1.4-mile round trip to a frozen waterfall). Medium-length hikes include the 4-mile Rose River Falls loop near Big Meadows and the 3.4-mile Chimney Rock Trail.

You’ll find plenty of cabins and lodges available for rent in the area, or you can book a stay at the stunning Keswick Hall for a unique experience.

Save it on Pinterest for later: