Chestnut Hill Holidays from AU$2,588

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Your Chestnut Hill Holiday

From its highlights to its hidden treasures, this city is best experienced with a Chestnut Hill holiday package. Find somewhere to stay in Downtown Boston, which is good for nightlife, shopping and bars and pubs. A trip to Chestnut Hill is an ideal opportunity to take in the sights. Check out big-name attractions such as Boston College, Agganis Arena and Paradise Rock Club. Whoever you're taking time off with and whatever you plan to spend, your dream Chestnut Hill holiday is just a few clicks away with Expedia.

The Latest Chestnut Hill Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
per person
4 Feb - 11 Feb
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
8.6/10 Excellent! (1,093 reviews)
Friendly and elegant!

Reviewed on 30 Nov. 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
4 Feb - 11 Feb
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.6/10 Exceptional! (1,075 reviews)
Very clean and quiet. Staffs are really helpful and nice

Reviewed on 1 Dec. 2024

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
per person
4 Feb - 11 Feb
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.2/10 Wonderful! (336 reviews)
Amazing all around!

Reviewed on 27 Nov. 2024

The Boxer

The Boxer

4 out of 5
West End
per person
4 Feb - 11 Feb
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
8.6/10 Excellent! (1,105 reviews)
Nice property, nice rooms, and restaurant / bar in hotel is nice. Excellent location to TD Garden.

Reviewed on 27 Nov. 2024

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
per person
4 Feb - 11 Feb
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
8.8/10 Excellent! (2,482 reviews)
The room had no cutlery or plates, even though it had a convenient kitchenette.

Reviewed on 2 Dec. 2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

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Chestnut Hill Holiday

Chestnut Hill Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Coolidge Corner Theatre, Larz Anderson Auto Museum and Larz Anderson Park

Our pick of the best Chestnut Hill Hotel Deals

Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$296 per night from 20 Dec to 21 Dec
AU$296
includes taxes & fees
20 Dec - 21 Dec
9.6/10 Exceptional! (2,609 reviews)
"Staff were great. Food in the hotel was great too. Clean room excellent all around. We loved it"

Reviewed on 1 Dec. 2024

Seaport Hotel Boston
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 AU$290 per night from 22 Dec to 23 Dec
AU$290
includes taxes & fees
22 Dec - 23 Dec
8.2/10 Very Good! (3,295 reviews)
"Love the Park Plaza. A great place to spend a night or two."

Reviewed on 28 Nov. 2024

Hilton Boston Park Plaza
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$356 per night from 6 Dec to 7 Dec
AU$356
includes taxes & fees
6 Dec - 7 Dec
8.6/10 Excellent! (2,880 reviews)
"Convenient downtown location"

Reviewed on 30 Nov. 2024

Omni Parker House
See all 3,189 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

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Chestnut Hill holiday package cost?
From as low as AU$2,588. Yes, you read that correctly. Our Chestnut Hill holiday packages are an easy way to make your budget go further. Combine your preferred flights, hotels and rental car and get out and see this lively destination.
How do I get a cheap travel package to Chestnut Hill?
Browse and book everything all in one place with our Chestnut Hill holiday packages. You’ll discover deals on hotels, flights and more that’ll keep your pocketbook happy and your adventurous spirit full. And, with more than 550 partner airlines and 1 000 000 properties globally to choose from, you’ll have the flexibility to mix and match as you want.
Where should I stay in Chestnut Hill?
A holiday in Chestnut Hill isn’t complete without stopping by Coolidge Corner Theatre, John Fitzgerald Kennedy National Historic Site and Larz Anderson Auto Museum. Stay near these attractions and make sightseeing a breeze.
What are the top hotels in Chestnut Hill?
If you intend to stay in the South Brookline neighbourhood, some top options are One Mile From Us Open Country Club and Avoid The Parking Hassle With 0. 8 Mile Away From Us Open. Woodland Heath is also a favourite Chestnut Hill area. We recommend Cosy Chestnut Hill 1br, Residential Area or Charming Chestnut Hill 2bedroom Nr Boston College T if you prefer this part of town.
How far in advance should I book my Chestnut Hill holiday?
While prices change from time to time, we generally advise booking your flight as early as possible. Most international fares can be compared on Expedia up to a year in advance. If you’re booking late, you may still get lucky. Low prices to Chestnut Hill sometimes emerge just weeks before departure.
What does an Expedia Chestnut Hill travel package include?
Choose from a combination of hotels, rental cars and flights. Once you’ve made your booking, you can add the fun stuff like activities and tours. Want to pick your fare class? That’s also easy to do. The choice is yours when it comes to crafting your ideal Chestnut Hill escape.
What should I know before booking a Chestnut Hill travel package?
When you book your flights, hotels and car rentals together, you’ll enjoy fantastic discounts. Whether you’re organising a beach escape in a villa or prefer to stay in a cosy apartment in the city, Expedia can help make it happen.
Can I choose my airline with a Chestnut Hill Expedia holiday package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines throughout the world. Our packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Chestnut Hill holiday package?
We totally get that life can throw you the odd curveball. If you’ve booked a Chestnut Hill holiday package and need to cancel or amend it, we’re here to help. We suggest browsing our Customer Service Portal first for information. But in general, if you’ve booked your package in the last 24 hours, you may be able to cancel or change your itinerary free of charge. If it’s been more than 24 hours, your hotel, airline or car rental company may charge a fee.

Discover the most popular places to visit in Chestnut Hill

Fenway Park which includes night scenes and a sporting event as well as a large group of people

Fenway Park

4.5/5(9 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University which includes heritage architecture and a city

Harvard University

4.5/5(27 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
New England Aquarium

New England Aquarium

4/5(7 reviews)

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium

What to do in Chestnut Hill

Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

AU$115
Per adult
76% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
Mysteries & Murders of Salem Guided Night-Time Walking Tour

Mysteries and Murders of Salem Guided Night-Time Walking Tour

AU$51
Per adult
92% of travellers recommend
Mysteries and Murders of Salem Guided Night-Time Walking Tour
North End Boston: 'The Mafia Mission' City Game

North End Boston Mafia Exploration Game and Tour

AU$16
Per adult
90% of travellers recommend
North End Boston Mafia Exploration Game and Tour
See all activities in Chestnut Hill
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.