Vacation Packages from Boston, MA

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Discover some of the best vacations from Boston

Boston is more than a city steeped in history; it's an ideal stepping stone to your next adventure. Dreaming of a tropical vacation from Boston? Florida's sun-soaked coasts, the Bahamas's untouched beauty, and Aruba's colorful vistas are just a plane ride away. For a quick weekend escape, New England's countryside beckons with quaint villages and nature retreats in driving distance. Or, for a deeper cultural experience, immerse yourself in the Caribbean's vibrant traditions or Ireland's lush landscapes and historic castles with easy direct flights. Wherever you're headed, some of the best vacations from Boston start with great deals on packages from Expedia.

Bask in the unmatched beauty of Aruba

Indulge in a tropical oasis with all-inclusive vacations from Boston to Aruba. With an average flight time of just under 5 hours from Boston, Aruba invites you to relax and recharge. Stroll down white-sand beaches, explore vibrant coral reefs, and savor the island's rich local cuisine. These Aruba vacation packages from Boston, ideal for 5 to 7 days, are your ticket to sunny skies, sparkling seas, and unforgettable adventures.

Sun, fun, and endless activities await in Florida

Dive into the warmth and wonder with vacation packages from Boston to Florida. With the average flight lasting 3 to 4 hours from Boston, you can swap cobblestones for inviting sands in no time. Immerse yourself in Destin's breathtaking sunsets, Orlando's thrilling theme parks, or Miami's bustling city life. Whether you're seeking discovery or relaxation, a 4 to 7-day stay is ideal for enjoying the endless Florida sunshine.

Embark on an enchanting journey to Ireland

Escape the urban landscapes of Boston for Ireland's lush, green countryside with flights averaging about 6 hours. Explore Dublin's historic streets, the majestic Cliffs of Moher, and the tranquil beauty of the Ring of Kerry. Whether you're looking to dive into rich history, local pubs, or remarkable scenery, Ireland vacation packages from Boston, recommended for 5 to 9 days, are your ticket to experiencing the country's magic.

Dive into the Caribbean's crystal waters

Discover crystal-clear seas and vibrant island culture with cheap vacations to the Caribbean from Boston. Whether you're drawn to the lively streets of Jamaica or the tranquil hideaways of Barbados, average flights take 3 to 5 hours, depending on your chosen destination. Indulge in a 4 to 7-day retreat or an all-inclusive Caribbean vacation from Boston, ensuring a harmonious blend of adventure and relaxation.

Discover the Bahamas' tropical paradise

Immerse yourself in sun-soaked beaches, crystal-clear waters, and rich culture in the Bahamas, with average flights running about 3 to 4 hours from Boston. Whether you're seeking a romantic retreat, a family adventure, or an all-inclusive vacation from Boston to the Bahamas, opting for a 3 to 7-day stay ensures ample time to experience the beauty and attractions of the islands.

How to Get Great Deals on Weekend Getaways and Vacation Packages from Boston

Vacation packages from Boston

We have many options for vacation packages from Boston with deals on hotels, flights, and cars, and you’ll earn extra savings by bundling. Take the family on an Orlando vacation or treat your partner to a romantic vacation in Niagara Falls. Customize your journey and select hotels, flights, and cars that best suit your budget and your needs. Compare prices for different dates and locations and use our many search features.

 

Weekend getaways from Boston

Take off for a quick jaunt from the city to experience luxury hotels, cheap stays, and more. With Expedia’s weekend vacation packages from Boston, you could head to the beaches of Cape Cod or forests of Vermont. Discover Maine with a romantic weekend vacation package, spent cycling the coast and dining on the waterfront. Or see pristine beaches and countless lighthouses with an excursion to Nantucket, MA. For family weekend getaways from Boston, consider the Hudson Valley or Pocono Mountains, where you can go horseback riding or try rock climbing and archery.

 

The best road trips from Boston

Discover incredible road trips from Boston for a great price on Expedia. Combine car rentals with hotels in one of our vacation packages from Boston for couples to Martha’s Vineyard romantic hotels. Plan a New England road trip from Boston to NYC with friends and stop in Cape Cod and Newport along the way. We have packages for luxury hotels and prestige vehicle rentals in our vast inventory, or cheap cars and budget hotels.

 

All-inclusive vacations from Boston

Take all-inclusive vacations from Boston and get all your costs upfront. Get meals, drinks, taxes, and fees included in the hotel price and score additional discounts by bundling travel bookings together.

We have fantastic deals for all-inclusive hotels in Miami. Bundle your favorite hotel with a car rental and/or flights to save even more. All-inclusive vacations from Boston to popular beach spots are great for families, couples, and friends. Save by getting meals and drinks included, plus extra discounts on your overall trip cost with a package. Check out vacation packages to Costa Rica to get started.

 

Boston winter vacations

Take the family on winter getaways from Boston to popular ski destinations like New Hampshire or Vermont. Or plan a holiday for the holiday season in beautiful cities to celebrate in, like Washington D.C., or New York City. There are many wonderful destinations to take weekend getaways from Boston in the winter.

 

Last-minute vacation deals from Boston

Expedia has last-minute vacation deals from Boston. We source offers for all travelers at attractive prices—even if you are late in the game. Our deals on last-minute getaways from Boston find you savings on properties of all types. And whether it’s a spontaneous trip with your sweetheart or a delayed flight that’s got you traveling, find what you’re looking for on Expedia. We have a large inventory of travel options across various budgets and catering to many different types of experiences. Find cheap hotels close to airports, luxury stays in the best locations, or accommodations in all the towns you stop at along your road trip.

 

Flexibility and cancellation

Find information about your vacation booking in your itinerary under ‘My Trips.’ To book flexible getaways, choose hotels or car rentals with ‘free cancelation’ and flights with ‘no change fees.’ Learn more at our customer service portal

All you need to know about vacations from Boston

Where to go for spring break from Boston?

Bostonians seeking an unforgettable spring break have a world of options suited to every preference. Craving a beach escape? The tropical paradises of Aruba or the Bahamas beckon with enticing deals on all-inclusive vacations from Boston. For a taste of vibrant city life, consider escaping to the cultural hotspots of New Orleans or nearby New York City. Seeking an adrenaline-filled adventure within driving distance? Head to the slopes of Vermont or New Hampshire for late-season snowboarding or skiing.

What is the closest country to fly to from Boston?

For Bostonians eager to venture beyond US borders, Canada stands as the closest country to fly to from Boston. Just a short flight away, cities like Montreal, Toronto, and Quebec City offer rich cultural experiences, historic landmarks, and culinary delights. Whether you're craving poutine in Montreal or exploring the vibrant street art scene in Toronto, Canada provides a convenient and accessible international escape. Explore last-minute vacations from Boston and discover the charm of the US's northern neighbor.

What Caribbean island is closest to Boston?

Among the Caribbean islands, the Bahamas is the closest island getaway to Boston. Just around 1,250 miles south of the city, the Bahamas beckons with an unforgettable beach vacation from Boston. Snorkel among colorful coral reefs, explore historic sites, or simply relax on the sandy shores. Whether you're embarking on a romantic retreat, an island-hopping adventure, or a cruise vacation from Boston, a convenient and captivating island getaway awaits. Grab your bathing suit, pack your bags, and embark on an enchanting journey to the Bahamas.

What tropical island is closest to Boston?

The idyllic island of Bermuda is the nearest island retreat to Boston, lying just over 1,000 miles southeast of the city. Nestled in the Atlantic Ocean, Bermuda vacations from Boston entice visitors with breathtaking pink-sand beaches, picturesque pastel-colored architecture, and crystalline turquoise waters. Whether you're seeking a tranquil winter vacation from Boston's hustle, eager to tee off on world-class golf courses, or yearning to scuba dive through vibrant underwater ecosystems, Bermuda promises unparalleled bliss.

Can you fly direct to the Azores from Boston?

Yes, travelers departing from Boston can enjoy direct flights to the Azores, a stunning archipelago located in the North Atlantic Ocean. Several airlines offer nonstop flights from Boston Logan International Airport to the Azores, making it easy to immerse yourself in the volcanic islands' rugged beauty, lush landscapes, and rich Portuguese heritage. Whether you prefer hiking along scenic trails, exploring charming coastal villages, or soaking in natural hot springs, direct flights make discovering the Azores' enchanting wonders one of the best vacations from Boston.

Can you fly direct from Boston to Italy?

Yes, you can enjoy direct flights from Boston Logan International Airport to various destinations in Italy. Several airlines offer nonstop flights to popular Italian cities such as Rome, Milan, Venice, and Florence, providing convenient access to Italy's rich history, dynamic culture, and world-class cuisine. For hassle-free travel, vacation packages from Boston are available, which conveniently bundle flights and accommodations to Italy's iconic cities. Additionally, last-minute vacation deals from Boston offer spontaneous travelers the opportunity to explore this stunning country at affordable prices.

Can you fly direct to Costa Rica from Boston?

Yes, direct flights from Boston to Costa Rica are available, offering you a convenient way to explore the lush rainforests, pristine beaches, and diverse wildlife of this Central American gem. Several airlines operate nonstop flights from Boston Logan International Airport to Costa Rica's main airports, including San José and Liberia. If you're seeking some of the cheapest vacations from Boston, budget-friendly package deals on Expedia bundle flights, accommodations, and activities at more affordable prices. That way, you can enhance your Costa Rican getaway without breaking the bank.

How long does it take to fly from Boston to Las Vegas?

Flights from Boston to Las Vegas typically take 5 to 6 hours on average, depending on departure and arrival airports, as well as layovers. From exploring iconic casinos to dining at acclaimed restaurants and experiencing thrilling nightlife, Las Vegas vacations from Boston can be tailored to every traveler. Seeking cheap vacations from Boston? Expedia's wide range of budget-friendly packages, including top deals on flights, stays, and entertainment, are a great way to save on travel costs.

Why book a vacation package from Boston with Expedia?

Booking a vacation package from Boston with Expedia offers numerous benefits, including convenience, savings, and flexibility. Our vacation packages often bundle flights, hotels, and rental cars together, allowing you to unlock better deals than booking each element separately. Whether you're dreaming of a cross-country road trip with your partner, a fun-filled family adventure on the beach, or a quick weekend vacation from Boston with your friends, vacation packages allow you to customize a great getaway from Boston with ease.

Can I cancel my vacation from Boston booking?

Yes, Expedia offers flexible cancellation options for vacation bookings from Boston. However, it's important to keep in mind that your specific cancellation policy depends on the terms set by the travel providers involved, such as airlines, hotels, and rental car companies for your booking. During the planning process, review your reservation's provided cancellation policy information to make informed decisions and book with peace of mind. Remember that some reservations may be refundable with certain conditions or incur fees for cancellations or changes.