Chestnut Hill Holidays from AU$2,652

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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.

Top Holiday Package Deals in Chestnut Hill

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was AU$3,392, price is now AU$2,652 per person
AU$2,652
per person
21 Apr - 27 Apr
found 17 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
Everything was perfect! No complain.

Reviewed on 1 Mar 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was AU$6,679, price is now AU$4,295 per person
AU$4,295
per person
21 Apr - 27 Apr
found 17 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on 25 Jan 2026

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
Seaport District
Price was AU$4,872, price is now AU$3,701 per person
AU$3,701
per person
21 Apr - 27 Apr
found 17 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
9.2/10 Wonderful! (4,205 reviews)
Friendly staff. No issues. Room was very clean. Easy access to our event across street.

Reviewed on 1 Mar 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was AU$4,368, price is now AU$3,455 per person
AU$3,455
per person
21 Apr - 27 Apr
found 17 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
This stay was really nice!

Reviewed on 1 Mar 2026

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was AU$5,825, price is now AU$4,810 per person
AU$4,810
per person
21 Apr - 27 Apr
found 17 hours ago
Return flight included
Brisbane (BNE) to Boston (BOS)
9.4/10 Exceptional! (536 reviews)
Outstanding venue and staff.

Reviewed on 16 Feb 2026

Our guide on 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 showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(17 area reviews)

This is Boston’s business district, now and back when the city was just starting.

Find hotels in Downtown Boston

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$255 per night from 8 Mar to 9 Mar
AU$255
8 Mar - 9 Mar
includes taxes & fees
9.6/10 Exceptional! (4,023 reviews)
I love this hotel. The staff is exceptional. They are friendly, professional and very attentive. The food was amazing and my room was clean, quiet and I had a great view. I will definitely stay there again.

Reviewed on 1 Mar 2026

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$301 per night from 8 Mar to 9 Mar
AU$301
8 Mar - 9 Mar
includes taxes & fees
9.2/10 Wonderful! (4,478 reviews)
Pleasant and helpful staff. Clean room and excellent location.

Reviewed on 2 Mar 2026

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 AU$278 per night from 22 Mar to 23 Mar
AU$278
22 Mar - 23 Mar
includes taxes & fees
8.4/10 Very Good! (3,111 reviews)
Yes the room was very clean. And very comfortable for a small room. The shower's tight. I think that is the only Town side to the wicked small room. I stay here a lot. The staff is always top notch. Love the little sitting room with the fire it's. Very uncomfortable. Always enjoy staying here.

Reviewed on 2 Mar 2026

Hilton Boston Park Plaza
See all 3,993 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
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beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Chestnut Hill holiday package cost?
You can snap up a holiday package to this popular destination from AU$2,652 on Expedia. However, how much your holiday to Chestnut Hill costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Chestnut Hill?
If you'd like to score a cheap Chestnut Hill holiday package, consider travelling in January, February and November. You'll usually find lower rates on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Chestnut Hill?
The ideal duration of your Chestnut Hill holiday depends on what you'd like to see and do. Typically, a few days to a week will give you plenty of time to hit all the leading attractions and discover some hidden spots along the way.
How to find the best Chestnut Hill package deals?
Start your search for a Chestnut Hill package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Chestnut Hill package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chestnut Hill getaway off to a flying start.
Is it cheaper to book a Chestnut Hill holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and stays separately. Better still, you can tailor your Chestnut Hill trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Chestnut Hill?
If you have your Chestnut Hill holiday dates locked in, book early to snap up some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Chestnut Hill?

  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Chestnut Hill.
  2. Work out your budget: Make sure you have enough money to cover everything from dining out and transportation to airfares and activities. Your accommodation will probably be the largest expense during your trip to Chestnut Hill.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Chestnut Hill. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Chestnut Hill holiday package that brings all your bookings together.

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

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

Fenway Park
Boston Common which includes landscape views, a skyscraper and a park

Boston Common

The oldest public park in the United States, Boston Common is the ideal place to relax, unwind and soak up some history.

Boston Common
Harvard University which includes heritage architecture and a city

Harvard University

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

Harvard University

Activities

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

AU$74
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston Tea Party Ships Museum with costumed tour guide in Boston

Boston Tea Party Ships & Museum Experience

AU$45
per adult
96% of travellers recommend
Boston Tea Party Ships & Museum Experience
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

AU$33
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
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.