Vacations in Boston

Vacations in Boston

2 travelers
Mon 4/1
Thu 4/4

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Cheap Boston package deals

Most popular Boston flight and hotel deals

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Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Chicago O'Hare Intl
Meals not included
3 nights + flight
$889
Dorchester
Free Wi-Fi
Philadelphia
Meals not included
3 nights + flight
$379
Waterfront
Free Wi-Fi
Pool
Pet friendly
Spa
Chicago O'Hare Intl
Meals not included
3 nights + flight
$469
West End
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
$354
Brighton
Pet friendly
Memphis
Breakfast
3 nights + flight
$388
Hotel Commonwealth
8.7 Very good
Fenway–Kenmore
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$507
400 Columbus Avenue - Boston - Living room
400 Columbus Avenue - Boston - Living room
400 Columbus Avenue
South End
Chicago O'Hare Intl
Meals not included
3 nights + flight
$334
East Boston
Airport shuttle
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$404
Bay Village
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
$290
Raffles Boston - Boston - Lounge
Raffles Boston - Boston - Lounge
Raffles Boston
9.6 Wonderful
Back Bay
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$847
Yotel Boston
8 Very good
South Boston
Free Wi-Fi
Philadelphia
Meals not included
3 nights + flight
$275
Boston Harbor Hotel
8.9 Very good
Waterfront
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$837
West End
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$444
The Boxer
8.1 Very good
West End
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$431
West End
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$569
Waterfront
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$525

When to book a vacation in Boston

Price includes flights and 3 nights accommodation for 2 travelers. Prices are not fixed and may vary with time.

Tips for finding Boston package deals

  • There are loads of types of vacations in Boston and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travelers: Top vacation $465; Family vacation $377; Romantic vacation $522; Luxury vacation $576; Budget vacation $325.

Why should you book a vacation package to Boston?

From American history to renowned cultural and educational institutions, fantastic seafood and a thriving foodie scene, there is so much to do in Boston that you'll need to book more than one trip. Walk the Freedom Trail of historic sites, or wile away the afternoons in one of the many museums and galleries. Boston vacation packages can save you money and time, so you can focus on researching all the city has to offer to make the most of your trip.

When should you book a vacation package to Boston?

While the winter can be formidable, mild spring and fall weather makes the best time to visit Boston between June and October. Hotels and flights are most expensive during July and August, with many crowds of tourists, but it's also when the popular baseball season is active, and there are many outdoor concerts and other events. The cheapest flights for Boston getaways can be found during January and February.

Where should you stay in Boston during your vacation?

For any vacation type in Boston:

Boston flight and hotel packages can include the very best of the city. Loews Boston Hotel is a classic slice of Beantown, housed in the building that was once Boston Police Headquarters. It offers authentic Old Boston luxury in the Back Bay area of the city, just over five miles from the airport. A taxi is your most convenient route back and forth. The Eliot Hotel sits right in the heart of Boston, with a stylish take on historic design and decor. Logan International Airport is just over six miles away, with subways or taxi transfer available.

For family vacations in Boston:

Boston vacation deals can save you money on family fun. For a luxury family vacation, the Boston Marriott Long Wharf offers a stunning waterfront with an indoor pool and a location close to the New England Aquarium and other major attractions. It's less than 3 1/2 miles from the airport, with a taxi the most convenient choice of transport. Kids come first at the Hotel Marlowe in historic Cambridge. The rooms are newly renovated and comfortable, and the hotel offers a number of kid-friendly amenities, including babysitting services. It's about four miles and an easy taxi ride from Logan Airport.

For romantic vacations in Boston:

Hide away from the everyday world in the opulent contemporary decor of the Ritz Carlton, located in the Theater District near the city center with its shopping streets and multiple dining and nightlife options. It's about 4 1/2 miles or a 15 minute taxi ride from Logan Airport. The Envoy Hotel, Autograph Collection is bold and stylish, with spectacular views of the waterfront in the Seaport district. It's under 3 miles from Logan Airport, and transportation can be arranged via the hotel concierge.

For luxury vacations in Boston:

In Beacon Hill and near Boston Common, the XV Beacon Hotel offers modern luxury in a stylish boutique property just steps from luxe shopping, dining, and the best of the city, less than a 3 mile taxi ride from Logan Airport. With sophisticated modern decor and sweeping views of the Charles River and the Boston skyline, the Royal Sonesta Boston is an escape from the bustle of the city, but still just minutes from the center, with taxis readily available for the 15 minute drive to the airport.

For budget vacations in Boston:

Inexpensive Boston vacation packages make the city accessible to any budget. For a bohemian, rock 'n roll take on Boston, the Verb Hotel is colorful and casual, and located near Fenway Park. It's about 4 1/2 miles from Logan Airport, with multiple transfer options including bus, taxi, and airport shuttle. The Boston Park Hotel offers budget friendly accommodations near Boston Public Gardens and across from Boston Common. The hotel is located on the T subway line at the Arlington Street Station.

Where to stay in Boston

Our map will help you find the perfect place to stay for your vacation in Boston by showing you the exact location of each hotel.

Boston vacation information

Top vacation (Flight+Hotel)$465
Family vacation (Flight+Hotel)$377
Romantic vacation (Flight+Hotel)$522
Luxury vacation (Flight+Hotel)$576
Budget vacation (Flight+Hotel)$325