
Chestnut Hill Vacation Packages
Book a Stay + Flight or Car to save on your trip
Chestnut Hill Vacation Packages
Chestnut Hill Vacation Packages
If you'd like to combine your hotels and flights to stretch your dollar, you're in the right place! Just kick back, take a load off and let the team at Orbitz help you create an amazing Chestnut Hill vacation. Think of all the cash you'll save by packaging your bookings. Choose your preferred hotels, rental cars, airfares and experiences and you can save up to $374! And we're not done! With 500,000 hotels across the world and 500 airline partners, you'll have plenty of freedom to pick and choose. There are limitless possible options to design your own amazing vacation, no matter your style, budget or interests.
Where is Chestnut Hill?
Losing your way in a foreign place sounds romantic. But if you want to get to Chestnut Hill on the first try, listen up. The neighborhood sits 6 miles southwest of downtown Boston, the state capital of Massachusetts. The population of Boston is roughly 600,000.Places to Visit in Chestnut Hill
Humans can't live without trees, but there's plenty about these pillars of our landscape that many of us are clueless about. Find out a few of the secrets of these arboreal wonders at Arnold Arboretum. Need some more nearby options? Pay a visit to Larz Anderson Auto Museum for a ride into the past! There's still more to see! Look into the lovingly preserved rooms and visualize how the former inhabitants of Frederick Law Olmsted National Historic Site used to live. This house gives its visitors an unusual historical insight.
Car Rentals in Chestnut Hill
Take your travel lust further by checking out car rentals in Chestnut Hill. No matter where you go or what you'd like to do, Orbitz will help you find a rental that fits your adventurous spirit. If you're eager to start the adventures as soon as the plane lands, rent a car from the Logan International Airport area. Make your way to Advantage Rent-A-Car and Enterprise. Enterprise is only 3 miles from the middle of town at 4009 Washington Street. So if you want to hit the busy city streets, you know where to go. Another favoured rental outlet located 3 miles from the town center is Hertz at 414 Cambridge Street.
Places to Visit in Chestnut Hill
Humans can't live without trees, but there's plenty about these pillars of our landscape that many of us are clueless about. Find out a few of the secrets of these arboreal wonders at Arnold Arboretum. Need some more nearby options? Pay a visit to Larz Anderson Auto Museum for a ride into the past! There's still more to see! Look into the lovingly preserved rooms and visualize how the former inhabitants of Frederick Law Olmsted National Historic Site used to live. This house gives its visitors an unusual historical insight.
Nearest Airports to Chestnut Hill
If you're setting out for Chestnut Hill, chances are your trip will begin at Logan International Airport (BOS), which is 8 miles to the northeast. Once you've landed, pick up your suitcase and kick off your next unforgettable adventure!
Popular Places to Visit Near Chestnut Hill
Cleveland Circle and Brookline are well worth visiting while you are here. Cleveland Circle is 1 mile away, and Brookline is 2 miles away.
No Cancellation Fees
Feeling a bit fed up because you need to cancel your trip? Don't stress — we're not going to add to your pain by charging you a fee.^ If you act fast, your chosen hotel and airline might not either.
Top Chestnut Hill vacation package deals

Club Quarters Hotel Faneuil Hall, Boston
Jan 23 - Jan 26
Dallas (DFW) to Boston (BOS)
Reviewed on Oct 13, 2025

Boston Harbor Hotel
Jan 23 - Jan 26
Dallas (DFW) to Boston (BOS)
Reviewed on Mar 24, 2024

DoubleTree Suites by Hilton Hotel Boston - Cambridge
Jan 26 - Feb 2
Phoenix (PHX) to Boston (BOS)
Boston (BOS) to Phoenix (PHX)
Reviewed on Aug 8, 2025

The Newbury Boston
Jan 2 - Jan 7
Dallas (DFW) to Boston (BOS)
Boston (BOS) to Dallas (DFW)
Reviewed on Jul 3, 2023

Embassy Suites Boston Logan Airport
Jan 23 - Jan 26
Dallas (DFW) to Boston (BOS)
Reviewed on Aug 6, 2025
Top rated hotels for your Chestnut Hill vacation package

Seaport Hotel Boston

The Revolution Hotel

citizenM Boston North Station
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