40 Fantastic Weekend Getaways from Boston for Every Season The Boston area is a great place to live, but sometimes you just need to get away! Before you sit down and wrack your brain for ideas just to come up with the same old, same old or think of places that are “too cold”, “too hot”, and “too far”, take a look at this list of weekend getaways from Boston. We have broken it down by season to make it easy. And since no one wants to spend their whole weekend in transit, we have only included destinations that are about four hours or less from Boston either by car or flight (mostly direct.) Read on for ideas on where to stay, what to do, and how to get to your next weekend getaway — whether you are traveling with kids or just the grownups. Table of Contents Winter Weekend Getaways from BostonJay Peak, VermontWhite Mountains, New HampshireStowe, VermontBethel, MaineBerkshires, MassachussettsNashville, TennesseeOrlando, FloridaNew York City, New YorkFort Lauderdale, FloridaSan Juan, Puerto RicoSpring Weekend Getaways from BostonBermudaProvincetown, Massachusetts Chatham, MassachusettsBeacon, New YorkProvidence, Rhode IslandNewport, Rhode IslandWashington DCSavannah, GeorgiaCharleston, South CarolinaClearwater, FloridaSummer Weekend Getaways from BostonMontreal, QuebecQuebec City, QuebecBlock Island, Rhode IslandPortland, MaineSmugglers Notch, VermontBurlington, VermontMoosehead Lake, MaineHalifax, Nova ScotiaChicago, IllinoisNantucket, MassachusettsFall Getaways from BostonMystic, ConnecticutManchester, VermontWoodstock, VermontLake Winnipesaukee, New HampshireLitchfield Hills, ConnecticutBar Harbor, MaineMartha’s Vineyard, MassachusettsRaleigh, North CarolinaBaltimore, MarylandCatskills, New YorkDon’t Forget Travel Insurance Winter Weekend Getaways from Boston Omni Mt. Washington, Bretton Woods, New Hampshire This post was written in partnerships with Allianz Travel. I have purchased Allianz Travel Insurance for my entire family for the last three years and they haven’t let me down yet! Note: This post contains affiliate links. If you click a link and make a purchase, we may receive a small commission at no cost to you. Please see our disclosure policy for more information. All opinions are my own. Jay Peak, Vermont Distance from Boston: 4 hours driving time Jay Peak Resort in Vermont’s Northeast Kingdom nearly bumps up against the Canadian border. Of course it is great in the summer and fall too, but because it gets so much snow, it is a perfect spot for winter sports enthusiasts. You will find skiing, snowboarding, Nordic skiing, snowmobiling, ice skating, snowshoeing, fat biking, and more. If indoor activities are more your jam, Jay Peak offers a movie theater, climbing gym, spa, arcades, and a giant indoor water park. Where to stay: Jay Peak Resort White Mountains, New Hampshire Distance from Boston: 2.75 hours driving time to Lincoln, 3 hours to Bretton Woods The White Mountains of New Hampshire work for many seasons, but really have something special to offer in the winter. Near Lincoln you will find the gorgeous Ice Castles installation (check website for dates as they vary by season) and at nearby Loon Mountain you will find snow tubing, skiing, snowboarding, and more. If you head to North Conway, you can relax after days outside at the indoor waterpark at the Red Jacket Mountain View Resort. While up at Bretton Woods, you can enjoy a horse drawn sleigh ride. See more options for skiing within three hours of Boston. Where to stay: Riverwalk Resort at Loon Mountain, Omni Mount Washington Resort Stowe, Vermont Distance from Boston: 3.25 hours driving time Stowe offers the small-town charm that is good for skiers and those that aren’t such fans of winter sports. With an option of ski resorts and inns within a short distance, it is a good home base for exploring some of Vermont’s specialties. These include sampling local craft beer at Bench, munching on warm apple cider donuts at the Cold Hollow Cider Mill, sampling cheese at Cabot Creamery, or making a pilgrimage to the Ben & Jerry’s Factory. Where to stay: Stoweflake Mountain Resort and Spa, Trapp Family Lodge, Topnotch Resort Bethel, Maine A snow storm on Upper Dreammaker at Sunday River Distance from Boston: 3.25 hours driving time Bethel is home to one of Maine’s largest ski resorts, Sunday River. Sunday River offers up 84km of trails across 15 lifts, with options for skiers, boarders, beginners, and thrill seekers. This resort is also ideal for families with ski-in/ski-out accommodations, a top-notch ski school, and family-friendly activities. Those that don’t ski can enjoy snowmobiling, snow tubing, snowshoeing, and even dog sledding! Where to stay: Grand Summit Hotel, Fallline Condos Don’t forget to purchase travel insurance for your trip! You never know what is going to happen with winter weather and illnesses. Berkshires, Massachussetts Distance from Boston: 2.25 hours driving time The Berkshires may be most well-known for the Boston Pops summer concerts at Tanglewood, but these mountain towns also make for a great winter destination. There is skiing and winter fun at Jiminy Peak with a “Fire and Fun Zone” and the exhilarating mountain coaster. There is more adventure to be found at nearby Ramblewild, which is open through the winter. But if you prefer to stay inside, pop into the many shops and galleries in Stockbridge and Lenox, or sample a few of the areas museums, like MassMOCA in North Adams. Where to stay: The Williams Inn, Wheatleigh, Seven Hills Inn Nashville, Tennessee Distance from Boston: Less than three-hour direct flight on Southwest, JetBlue, or Delta Sometimes you just need to get away from Boston in the winter, so we are including options that have a direct flight that is less than four hours. Nashville is often a destination in Southwest Airline’s Fare Deals and is a perfect spot for a weekend getaway. Music City offers so much from the Country Music Hall of Fame, to the Grand Ole Opry, and countless honky tonks offering live music on Broadway. Foodies will also love exploring Nashville’s food scene, which is as hot as its famous hot chicken. Where to stay: Union Station Hotel, The Westin Nashville Orlando, Florida Distance from Boston: 3.5 hours direct flight time on Southwest, Delta, JetBlue, Spirit, and Frontier Winter is a great time to hit the theme parks, when temperatures are cooler and lines are shorter (as long as you avoid holiday breaks). But there is also so much more to do beyond the theme parks in Orlando. Just getting to see palm trees and blue skies makes for a good weekend away! Where to stay: Margaritaville Orlando, Wyndham Grand Orlando Resort Bonnet Creek New York City, New York Distance from Boston: 3.75 hours on Amtrak’s Acela train Everyone loves New York City at Christmas, but January is actually a great time to visit NYC. Sure, the weather may be miserable but the hotel prices are and their lowest and there is plenty to do inside. Just grab a CityPASS and start exploring. Plus, NYC Broadway Week in late January (get your show tickets in advance), which makes it a great time to catch a show. Where to stay: The Knickerbocker (when seeing a show on Broadway), The New York EDITION Fort Lauderdale, Florida Distance from Boston: 3.5 hours direct flight on JetBlue, Spirit, and Delta When you want to trade grey skies for blue and snow for sand, a direct flight to Fort Lauderdale makes an easy weekend getaway. Even if it isn’t warm enough to hit the beach, palm trees have a way of putting everyone in a good mood. You can also enjoy airboat rides, alligator tours, kayaking, food tours, boat charters, and more. Where to stay: B Ocean Resort, W Fort Lauderdale San Juan, Puerto Rico Distance from Boston: 4 hour direct flight on JetBlue Catch a direct flight to San Juan for a weekend in the Caribbean — without a passport! You can explore Old San Juan, walk the Paseo del Morro, enjoy some street food, or hit the beach. Plus you will be helping this community make a recovery from the devastating hurricane that hit in 2017. Where to stay: Caribe Hilton, Embassy Suites by Hilton San Juan Spring Weekend Getaways from Boston Don’t forget to purchase travel insurance for your trip! No matter how long your trip, unforeseen circumstances can always come into play and it is better to be prepared! Bermuda Horseshoe Beach in Bermuda Distance from Boston: 2 hour direct flight on JetBlue Bermuda feels like it is in the Caribbean, but it is actually in the Atlantic Ocean, off the coast of North Carolina. Yet a two-hour flight will put your toes digging into the famous pink sand of Bermuda’s beaches. It can be chilly in the winter, but spring is prime-time for visiting this British Overseas Territory. Just remember that tourists aren’t allowed to rent cars, so you want to pick a resort with beach access and plenty to do. Where to stay: Fairmont Southampton Provincetown, Massachusetts Distance from Boston: 1.5 hour ferry ride In the summer, a trip to Provincetown means crowds, high prices, and limited availability. But if you visit the off-season, you can enjoy this charming town without the hustle and bustle. So when the weather starts warming up, hop on the ferry and head to P-town. Whether you book a bed and breakfast or one of the beach hotels, it is easy to walk through town and enjoy the many, many restaurants and shops. Where to stay: Sandcastle Resort, Lands End Inn Chatham, Massachusetts Distance from Boston: 1.75 hour driving time In the summer, you could spend two hours just sitting in traffic getting down to and across the Sagamore Bridge, but in the spring you can usually do the whole trip in that amount of time. There is still plenty to do on Cape Cod in the off-season, from the bike trails to visiting the museums or wildlife sanctuary. Even the whale watching cruises start heading out by late April. Plus, you won’t have to fight as hard to find a parking spot when shopping in downtown Chatham. Where to stay: Wequasset Resort & Golf Club, Chatham Bars Inn Beacon, New York Distance from Boston: 3.25 hours driving time Beacon in New York’s Hudson Valley has been a popular getaway for New Yorkers, but it is close enough to still make a good long weekend trip from Boston. This cute and quirky town on the Hudson River offers art galleries, boutiques, great restaurants, and nearby access to the cultural and historical treasures like the Dia: Beacon art museum and Franklin D. Roosevelt’s Presidential Library. If the weather is warm, you can also enjoy boat tours, kayaking, and more nearby. Where to stay: Roundhouse Providence, Rhode Island Distance from Boston: ~1 hour by car or Acela Amtrak train Providence is known as the “Creative Capital” for its hip dining and arts scene. Home to Brown University, Rhode Island School of Design and Johnson & Wales University, you can often find interesting festivals and events taking place, and the city’s famous Waterfire art installation kicks off in late spring each year. Book a gondola ride, enjoy Saturday morning farmers’ markets, poke through the wares at the Sunday morning Providence Flea, and spend an evening sampling some of the city’s new restaurants or food trucks. Where to stay: Dean Hotel, Graduate Hotel Newport, Rhode Island Distance from Boston: 1.5 hours driving time Spring can be an ideal time to visit Newport, before the yachts start showing up and the summer festivals get into full swing. Flowers bloom at the Newport Mansions and you can take in the panoramic view at places like Castle Hill Inn or Brenton Point State Park, rent a three-wheeled Scoot Coupe to explore Ocean Drive, and slurp down some fresh oysters at Midtown Oyster Bar. Where to stay: Gurney’s Newport Resort & Marina, Newport Marriott, The Vanderbilt Washington DC Distance from Boston: 1.75 hour direct flight on JetBlue, American, and Delta to Washington’s Reagan National Airport Washington D.C. may be crowded in the spring, especially when the cherry blossoms are in bloom, but it is also a special time to see the nation’s capital. Just plan ahead if you want to visit museums that require reservations, like the Holocaust Museum or the National Museum of African American History and Culture. It also is worth booking reservations for places like the Library of Congress, so you can skip the line upon arrival. Leave some time to enjoy the outdoors with a walk through the monuments or a bike tour along the Tidal Basin. Where to stay: The Darcy, The Mayflower Savannah, Georgia Distance from Boston: 2.75 hour direct flight on JetBlue Chippewa Square in Savannah If you are Irish or love to celebrate St. Patrick’s Day, head to Savannah for second largest parade in the U.S. Or, avoid the crowds and visit later in the spring when the weather is warm but not overly hot and humid. You can spend a couple of days exploring Savannah’s 22 squares, visiting historic homes, or visiting the country’s only Prohibition Museum. Evenings are spent walking along River Street or enjoying Savannah’s food scene. If you have some extra time, head out to Tybee Island for a beach day. Where to stay: Hotel Indigo Savannah, Hyatt Regency Savannah Charleston, South Carolina Distance from Boston: 2.75 hour direct flight on JetBlue or Delta Historic Charleston has become a bit of a food mecca in the south so on your visit, start off at the Farmer’s Market, then start sampling the local flavors on a food tour. When you get tired of eating and walking, hop on a carriage ride for a tour of the historic district’s houses and gardens. Spend your extra time shopping on King Street or exploring the coastal wetlands in a kayak or on a paddle board. Where to stay: Hyatt House Charleston, Hotel Bennett, Belmond Charleston Place Clearwater, Florida Distance from Boston: 3.5 hour direct flight on JetBlue, Delta, and Spirit The white sugar soft sands of Clearwater Beach draw visitors year round, but especially in April during the town’s Pier 60 Sugar Sands Festival. When not building sandcastles or taking part in the weekly activities offered downtime, you can hop on a pirate cruise, jump on a jet ski, or go visit Winter the famous dolphin at Clearwater Marine Aquarium. Where to stay: Wyndham Grand Clearwater Beach, Hyatt Regency Clearwater Don’t forget to purchase travel insurance for your trip! No matter how long your trip, unforeseen circumstances can always come into play and it is better to be prepared! Summer Weekend Getaways from Boston Montreal, Quebec Distance from Boston: 1.25 hour direct flight (or 5 hours driving time) Montreal is hopping in the summer. If there isn’t a festival going on, you can still ride bikes along the canal, go for a swim in Parc Jean-Drapeau, or partake in some of the many activities offered in the Old Port. If you venture beyond walking distance, the Botanical Gardens at Jardin Botanique are well worth the extra effort getting there. Don’t miss a stop at the Biodome across the street. While you are there, enjoy all the must-try foods like poutine, bagels, steak, and French pastries that you can. Where to stay: Fairmont The Queen Elizabeth, Le Westin Montreal Quebec City, Quebec Distance from Boston: <4 hours connecting flight through Montreal on Air Canada (or 6 hours driving time) Some places are worth either driving a little further or taking a connecting flight, and Quebec City is one of them. Quebec in the summer is host to music festival after festival, when everyone is happy to be outside in the sunshine! Walking around Old Quebec feels like exploring the cobblestone streets of a French town, full of charm and style. Where to stay: Fairmont Le Chateau Frontenac, Hilton Quebec Block Island, Rhode Island Distance from Boston: 3 hours driving time plus ferry ride If you are looking for a low-key summer weekend getaway, head to the “Block” on Block Island ferry. Things might seem a little crazy in town when you get off the boat, but rent a moped or a bike and head out to the pristine beaches and cliffs that make Block Island so special. When you are ready to party, head over to Ballards and enjoy a Bloody Mary or Mudslide while listening to music before heading back to the mainland. Where to stay: National Hotel, Avonlea Portland, Maine Distance from Boston: 1.75 hours driving time The “other Portland” is a bustling port town in the summer, full of tourists looking to enjoy some shopping, lobster rolls, and Maine’s craft beer (or blueberry soda.) If you want to escape the crowds, head out onto Casco Bay on the ferry or take a lobster boat tour (the Portland Lobster Company will cook what you catch!) Don’t miss a trip out of town to Cape Elizabeth and Portland Head Light or a stop in Kennebunkport on your way back to Boston. Where to stay: Press Hotel, Inn by the Sea Smugglers Notch, Vermont Distance from Boston: 3.75 hours driving time Smugglers’ Notch, affectionately known as “Smuggs” is a fun-filled, three-season resort, but you may be surprised how much there is to do in the summer. From mountain biking to zip lining, canoeing and kayaking, disc golf, and llama treks — the list of summer activities goes on and on. There are even some amazing summer camp programs for kids and teens. Where to stay: Smugglers Notch Resort Burlington, Vermont Distance from Boston: 3.25 hours driving time Explore the best of the Green Mountain state from the northern town of Burlington. This college town is located on the banks fo Lake Champlain (you can even take a ferry across to NY for a day trip to Ausable Chasm.) Nearby, you can visit the ECHO Aquarium & Science Center, Shelburne Museum, Ben & Jerry’s Ice Cream Factory, plus many local breweries, dairies, and farms. Where to stay: Hotel Vermont Moosehead Lake, Maine Distance from Boston: 4.25 hours driving time When you want to get away from it all, head north to Maine’s Lakes and Mountains region. Moosehead Lake, the largest in Maine, offers the peace and quiet you are looking for, while still offering plenty to do for outdoor enthusiasts. You can enjoy strenuous hikes, boating, and even moose safaris! Where to stay: Moosehead Hills Cabins, Lodge at Moosehead Lake Halifax, Nova Scotia Distance from Boston: 1.5 hours direct flight on Air Canada Direct flights into Nova Scotia land in Halifax, and you will want to spend some time exploring the many museums, galleries, and shops in town. Almost all visitors to Nova Scotia will want to head south to see the famous lighthouse at Peggy’s Cove, but head even further south to the UNESCO World Heritage Site at Lunenburg. If you have more time, you can drive the Cabot Trail or see the changing tides in the Bay of Fundy. Where to stay: Lord Nelson Hotel & Suites Chicago, Illinois Distance from Boston: 2.75-3 hour direct flight on JetBlue, United, Delta, American, Southwest, and Spirit Summer is a great time to visit the Windy City, when the sun is shining over Lake Michigan, making it more fun to enjoy the outdoors in Maggie Daley Park. Catch the view from the SkyDeck at the top of the Willis Tower, shop til you drop on the Magnificent Mile, score tickets to one of Chicago’s many theaters, or grab a CityPASS and head inside to the museums. Where to stay: The Gwen Hotel, Four Seasons Chicago Nantucket, Massachusetts Distance from Boston: .75 direct flight on Cape Air or JetBlue, or 3.5 mile driving time + ferry You don’t really need to bring your car to Nantucket, because the best way to explore is on a bike or scooter. Flat, paved bike paths will bring you to many of the island’s beaches. When exploring the island, don’t miss taking a walk along the Sconset Bluff Walk and visiting Nantucket’s three scenic lighthouses. Where to stay: Harborview Nantucket, White Elephant Fall Getaways from Boston Mystic, Connecticut Distance from Boston: 1.75 hours driving time The historic seaside town of Mystic is charming in the autumn when the fall colors are at their peak. It is easy to spend your time exploring the historic Mystic Seaport, shopping downtown or at Olde Mistick Village, and visiting nearby farms for the fruits of the harvest — and hot apple cider donuts! Where to stay: Spicer Mansion (adults only), Hyatt Place Mystic Manchester, Vermont Distance from Boston: 3.25 hours driving time Manchester must be one of the cutest towns in New England, offering something for shoppers or adventure seekers. Fall fun at nearby Bromley Mountain includes the alpine slide, zip line, and other thrilling attractions. Manchester also offers outlet shopping, antiques, and the noteworthy Northshire Bookstore. Where to stay: Kimpton Taconic Hotel, The Equinox Woodstock, Vermont Distance from Boston: 2.5 hours driving time The quintessential town of Woodstock is the perfect home base for exploring Central Vermont. Nearby you will find the more classic Vermont experiences like searching for covered bridges, tasting maple syrup at Sugarbush Farm, watching glass blowing at Simon Pearce, and hiking in the Quechee Gorge. Where to stay: Woodstock Inn and Resort Lake Winnipesaukee, New Hampshire Distance from Boston: 2.25 hours driving time Lake Winnipesaukee is the largest lake in New Hampshire, but there are plenty of others to choose from in the state’s Lakes Region. The obvious activities include boating, kayaking, paddle boarding, and fishing, but you can also enjoy zip lines, adventure courses, and hiking nearby before it gets too cold. Be sure to check out the early morning reflections of the fall colors in the lake or watch the sun set over the water. Where to stay: Mill Falls at the Lake Litchfield Hills, Connecticut Distance from Boston: 2.5 hours driving time Hike up to the top of Mt. Tom in Litchfield to find some of the prettiest fall views in Connecticut from the old stone tower at the summit. This region of Connecticut is known for its rolling hills, antique shops, art galleries, and picturesque towns offering bed and breakfasts and small inns, perfect for a weekend getaway. Where to stay: Mayflower Inn and Spa, Winvian Farm Bar Harbor, Maine Distance from Boston: 1.25 hour direct flight on Cape Air or JetBlue or 4.75 hour driving time Fall comes early in Bar Harbor, so you will want to plan your weekend getaway between mid-September and mid-October. Star gazers will enjoy the Acadia Night Sky Festival in September and hikers can enjoy trails that are often closed in the summer to protect nesting birds. Relax at the end of the day with a fresh lobster and one of Maine’s many local craft beers. Where to stay: Harborside Hotel Martha’s Vineyard, Massachusetts Distance from Boston: 2.5 hours driving time + ferry As lovely as beach destinations are in the summer, they are even better in the early fall when the temperatures are still pleasant but the crowds have left them behind until next year. You may even be able to get a reservation on a car ferry more easily! Fall is the ideal time to truly explore Martha’s Vineyard, from the clay cliffs of Aquinnah to sunsets at Menemsha and shopping in Edgartown. Where to stay: Harborside Inn Raleigh, North Carolina Distance from Boston: 2-2.25 hours direct flight on JetBlue, Delta, or Spirit When temperatures start to drop and you want to hold onto summer, head south to Raleigh, where Southern charm meets big city. You will find bike trails, lakes, hikes, plus local breweries, food halls, festivals, and sporting events. Where to stay: Aloft Raleigh, The StateView Hotel Baltimore, Maryland Distance from Boston: 1.5 hour direct flight on Southwest, Delta, American, United, JetBlue, or Spirit Baltimore’s Inner Harbor is lovely in the fall and if you time it right, you can catch an away game for the Red Sox or Patriots while you are in town. Explore the National Aquarium, take a harbor cruise, crack crabs in historic Fell’s Point, and grab breakfast at Miss Shirley’s before heading home. Where to stay: Kimpton Hotel Monaco, Pier 5 Hotel Baltimore Catskills, New York Distance from Boston: 4 hours driving time When you get tired of the mountains closer to home, head west to New York’s Catskills. In the fall you will find festivals, farms, beautiful foliage, and plenty of adventure including zip lines, adventure courses, and mountain biking. The area’s many cideries and breweries will give you plenty of excuse to take a scenic drive through the countryside. Where to stay: Kartrite Resort & Indoor Waterpark (for families), Inn at Lake Joseph Don’t Forget Travel Insurance Even weekend getaways need travel insurance to protect your investment, and yourself. My travel insurance provider of choice is Allianz Travel. For the last few years I have insured my family with an annual travel insurance plan and have purchased additional policies when extra coverage was preferred. I have had to make two claims, one trip cancellation due to illness (I got the flu!) and once for a trip delay when our original flight was cancelled and we had to rebook. Both claims went smoothly and I can check status and more on the Travel Smart app. Some of the things that travel insurance can protect for include: trip cancellation, trip interruption or delay, lost, delayed or stolen baggage, international healthcare, and travel assistance. Plans vary so find the best travel insurance plan for your trip at Allianz Travel. PIN THIS FOR LATER Find this useful? Share it!PinShareTweetFlipboardEmail Written by We3Travel and was last updated on January 6, 2020. Read more about Destinations, Massachusetts Related Posts Skiing Near Boston: 25 Mountains within a 3-hour Drive 20+ Family-friendly Museums in New England 10 Spooky East Coast Fall Family Getaways Be the first to comment Leave a Reply Cancel replyYour email address will not be published. Required fields are marked * Name * Email * Website This site uses Akismet to reduce spam. Learn how your comment data is processed.