Chestnut Hill Holidays from £957

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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.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
19 Sept - 26 Sept
found 6 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.6/10 Excellent! (2,132 reviews)
The room was nice and cozy, slept like a log all 3 nights.

Reviewed on 12 Aug 2025

Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
Save 100% on your flight
per person
15 Oct - 22 Oct
found 1 day ago
Return direct flight included
London (LON) to Boston (BOS)
8.6/10 Excellent! (1,070 reviews)
Spacious, comfortable room in a stylish hotel. Staff was nice and helpful.

Reviewed on 12 Aug 2025

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
per person
19 Sept - 26 Sept
found 6 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,679 reviews)
Staff was the most helpful and friendliest we have experienced in a while.

Reviewed on 13 Aug 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
19 Sept - 26 Sept
found 6 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (433 reviews)
Great small boutique hotel. European feel and service. Lovely small garden in back. Good food.

Reviewed on 11 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
24 Sept - 29 Sept
found 19 hours ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on 11 Aug 2025

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 which includes a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 area reviews)

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.

Find hotels in Downtown Boston

Top hotels in Chestnut Hill

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £206 per night from 24 Aug to 25 Aug
£206
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,822 reviews)
"Lovely upscale hotel. Staff are friendly, knowledgeable and helpful. This hotel is in an Ideal location, within walking distance walking distance of tourist attractions. Roof top pool is clean and enjoyable. The beds are comfortable, the bathroom and shower are clean and relaxing. I recommend staying ..."

Reviewed on 11 Aug 2025

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £170 per night from 1 Sept to 2 Sept
£170
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (3,196 reviews)
"The staff is great! The valet were absolute gentlemen! The folks at the front desk were lovely and, when I was lost trying to find parking, the young lady on the phone made me feel at ease, gave perfect guidance and even rooted me on by saying "you can do this!" And I can't forget the concierge who ..."

Reviewed on 9 Aug 2025

Hilton Boston Park Plaza
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £163 per night from 24 Aug to 25 Aug
£163
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (1,595 reviews)
"Great spot for a short stay. Advanced hotel with self check in and iPad to control the room. Compact room with a nice bed, tv, and shower. Walking distance to Fenway & lots of restaurants.. will stay again!"

Reviewed on 11 Aug 2025

citizenM Boston Back Bay
See all 3,616 properties in Chestnut Hill
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Chestnut Hill travel package cost?
The cheapest Chestnut Hill package is £957, 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.

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

£59
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

£52
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

£25
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Boston

* 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.