Chestnut Hill Holidays from £1,019
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Your Chestnut Hill Holiday
With plenty of highlights as well as hidden gems, this city is best experienced with a Chestnut Hill holiday package. Find somewhere to stay in Downtown Boston, which is great for nightlife, shopping and bars and pubs. Fill your schedule with visits to Boston College, Paradise Rock Club and Agganis Arena, some of the attractions you simply have to see during your trip to Chestnut Hill. Browse Expedia's wide range of travel options and start organising your perfect holiday to Chestnut Hill today.
Price found within the past 48 hours. Click for updated prices.
The Monty Boston
Downtown Boston
£1,599
per person
21 Nov - 27 Nov
found 9 hours ago
Return direct flight included
London (LHR) to Boston (BOS)
9.6/10 Exceptional! (40 reviews)
Amazing place for a group. It was super clean and a great location in Boston. It’s a city with homeless population so the only negative was the entrance way to the building smelled like pee. Nothing the building can do, but just something to know. I will defiantly stay there next time.
Reviewed on 3 Jul 2026
Where to stay in Chestnut Hill
Find the best Chestnut Hill areas and neighborhoods for the activities you enjoy most. Learn more about Chestnut Hill
Downtown Boston
The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.
Back Bay
1 out of top 10 points of interest in this area
Parisian boulevards and elegant brownstones conjure a truly romantic atmosphere, perfect for strolling and window shopping.
Seaport District
1 out of top 10 points of interest in this area
Join excited crowds enjoying harbor-side views, Revolutionary War-era landmarks, as well as superb restaurants and museums along this thriving waterfront.
Beacon Hill
1 out of top 10 points of interest in this area
Lose yourself in the charming streetscapes, historic buildings and village-like atmosphere of Boston’s oldest and wealthiest suburbs.
North End
The ample dining options and captivating waterfront views are just a few popular features of the neighbourhood. Make a stop by Boston Harbor or New England Aquarium while you're visiting, and jump aboard the metro at Aquarium to get around town.
Top hotels in Chestnut Hill
Seaport Hotel Boston
1 Seaport Lane Boston MA
£188
20 Sept - 21 Sept
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
£117
7 Sept - 8 Sept
includes taxes & fees
Harborside Inn Of Boston
185 State St Boston MA
£162
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (6,982 reviews)
"Nice hotel in good location, unfortunately water pressure in shower pretty poor."
Reviewed on 5 Sept 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does a Chestnut Hill travel package cost?
The cheapest Chestnut Hill package is £1,019, so your dream holiday can become a reality — without breaking the bank. Bundle flights, hotels and car rentals to customize a package that matches your travelling style.
If I'm not able to travel, can I cancel my Chestnut Hill travel package?
It is possible to cancel your Chestnut Hill booking if your travel plans have changed. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. It may be possible to change or cancel free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.
How do I get a cheap travel package to Chestnut Hill?
Track down flights that fit in with your schedule, add a hotel to your booking and watch the savings stack up with a Chestnut Hill travel package. It's as easy as that! From flights and hotels to rental cars and tours, Expedia is where your cheap getaway begins. And with over 550 airlines and 1,000,000 hotels around the globe to pick from, you won't be short of choice.
Does Expedia offer Book Now, Pay Later Chestnut Hill holidays?
Expedia has joined forces with online lender Klarna to make your next trip a little easier on the wallet. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more cash to spend while you're away. Klarna has several payment plans to pick from, so you're sure to find one that fits into your budget. Take a look at these flexible payment options:
- Pay monthly holidays: If paying small amounts each month sounds best for you, Klarna can help. Paying in easy monthly instalments will make your holiday dreams possible.
- Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Consider this Book Now, Pay Later option from Klarna.
- Low deposit holidays: When you come across an incredible deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock in your escape.
Where should I stay in Chestnut Hill?
A holiday in Chestnut Hill wouldn't be complete without visiting Boston College, St. Elizabeths Medical Centre and Brighton Music Hall. Spend your evenings near these popular sights and make sightseeing simple.
What are the top hotels in Chestnut Hill?
Make a reservation at Boston Park Plaza. It's one of the area's most popular properties. Another reputable option in Chestnut Hill is Embassy Suites Boston Logan Airport.
How far in advance should I book my Chestnut Hill holiday?
While not all airlines advertise ticket prices early, customers are usually able to look up international flights on Expedia up to a year in advance. This is when you'll score some fantastic bargains. If you're booking at the last minute, there's a chance you could get lucky. Discounted prices occasionally become available just weeks before departure.
What does an Expedia Chestnut Hill travel package include?
Expedia has all you need to organise your Chestnut Hill escape, but what goes into your package is up to you. Choose from a combination of hotels, flights and rental cars. Searching for a few activities to keep you entertained? Once you've made your booking, you can add them on too. Whatever your style, there's a package to meet your needs.
What should I know before booking a Chestnut Hill travel package?
So many places to venture to, so many things to see. With a travel package, you'll be able to afford more of them. Bundle your flights, hotels and rental cars and enjoy big savings.
Can I choose my airline with a Chestnut Hill Expedia travel package?
Yes, of course. Expedia has access to more than 550 partner airlines around the world, so fly with the carrier that fits your budget and travelling style.
Stay near popular Chestnut Hill attractions
McMullen Museum
6.0/10 (1 review)
This Boston College treasure houses over 5,000 artworks spanning diverse periods and cultures. Explore the serene galleries on Sunday afternoons for free docent-led tours of current exhibitions.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
£36
per adult
90% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
£34
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
£52
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.