Cheap Boston Vacation Packages

You’re on the hunt for a steal of a deal on your Boston vacation package. You’ve got your list of things you want, and you’re checking it twice: a ballin’ (on a budget) Boston hotel, a champagne poppin’ flight (for a knock-off beer price), and maybe even a super-nice car rental (for a borrowed bike fee).

Think it’s all just a dream? Not when you book your Boston vacation deal with Hotwire.

Are you for real with these vacation package deals

Daydreaming is even better when wildly good deals become your reality. Scoring hotel and flight deals to Boston for a price that works with your budget is realer than real when you book your package with Hotwire. Ready to get all of your wildest dreams fulfilled (for way less than you expected)? Don’t sleep on these Hotwire deals.

Frequently Asked Questions About Vacation Packages

How much is a vacation to Boston?

When you want to book the very best Boston getaway, but you aren’t looking to empty your bank account on planning your trip, cheap vacation packages are the way to go. You can jump into an incredible vacay to Boston for as low as $418 and keep your cash for the necessities—like the dreamiest fun times in town.

When is the best time to book a vacation package to Boston?

Looking to save some extra cash on your Boston vacation? Try going on your getaway in , which is the off-season, and avoid the most popular time to vacation in the month of . Want to get away now-ish and still save? Book a last-minute vacation package with a Hot Rate hotel deal. You could save up to 60% off on your hotel versus booking a listed rate two weeks earlier.

How to get the best vacation package deals to Boston?

If scoring the very best deal on your Boston vacation is at the top of your to-do list, book your package with Hotwire and prepare to get way more bang for your buck.

What is the cheapest day to book a vacation package?

Reserving a Boston vacation package on a Tuesday is the cheapest day to book, or you can save more any day on Hotwire, with packages as low as $418.

Can I vacation in Boston right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Boston right now?” When it’s time to book your vacation package, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

What does Hotwire Boston travel package include?

When you book a package deal on Hotwire, you can expect a Boston vacation package with airfare and hotel. Want a rental car too? No biggie‚ you can add it to your package. Everything you need for an amazing trip? Check.

Boston Flight + Hotel Packages

Hilton Boston Downtown/Faneuil Hall

Save 100% on your flight

per person

Mar 9 - Mar 12

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

Stay at this 4-star historic hotel in Boston. Enjoy breakfast, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and New England Aquarium are located nearby. Discover genuine guest reviews for Hilton Boston Downtown/Faneuil Hall, in Downtown Boston neighborhood, along with the latest prices and availability – book now.

The Godfrey Hotel Boston

Save 100% on your flight

per person

Mar 9 - Mar 12

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

Stay at this 4-star boutique hotel in Boston. Enjoy breakfast, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and Boston Common are located nearby. Discover genuine guest reviews for The Godfrey Hotel Boston, in Downtown Boston neighborhood, along with the latest prices and availability – book now.

The Revolution Hotel

per person

Mar 9 - Mar 12

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and Copley Square are located nearby. Discover genuine guest reviews for The Revolution Hotel, in South End neighborhood, along with the latest prices and availability – book now.

Freepoint Hotel Cambridge, Tapestry Collection by Hilton

per person

Mar 11 - Mar 16

Roundtrip non-stop flight included

Tampa (TPA) to Boston (BOS)

Stay at this 4-star business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast, and a free area shuttle. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Fenway Park and Copley Square are located nearby. Discover genuine guest reviews for Freepoint Hotel Cambridge, Tapestry Collection by Hilton along with the latest prices and availability – book now.

Moxy Boston Downtown, a Marriott Hotel

per person

Mar 9 - Mar 12

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

Stay at this 3.5-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and Boston Common are located nearby. Discover genuine guest reviews for Moxy Boston Downtown, a Marriott Hotel, in Downtown Boston neighborhood, along with the latest prices and availability – book now.

Hyatt Regency Boston/Cambridge

per person

Mar 9 - Mar 12

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

Stay at this 4-star hotel in Cambridge. Enjoy free WiFi, a 24-hour health club, and valet parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and Copley Square are located nearby. Discover genuine guest reviews for Hyatt Regency Boston/Cambridge, in MIT neighborhood, along with the latest prices and availability – book now.

Hyatt Place Boston/Medford

per person

Mar 16 - Mar 20

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

Stay at this 3-star business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and a free area shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and TD Garden are located nearby. Discover genuine guest reviews for Hyatt Place Boston/Medford along with the latest prices and availability – book now.

Hilton Boston Back Bay

per person

Mar 9 - Mar 12

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and Copley Square are located nearby. Discover genuine guest reviews for Hilton Boston Back Bay, in Back Bay neighborhood, along with the latest prices and availability – book now.