Chestnut Hill Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Ed Gaffny

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

Price found within the past 48 hours. Click for updated prices.
  • Standard Room, 1 Queen Bed
    Aug 17 - Aug 18

    Hotel Ivy Boston Common + Flight

    Bay Village
    1 night
    2.5 star property
    8.4/10 - Very good (1,473 reviews)
    "The cabinet was cool especially the little Cubby with switch and plug.Also loved the photo around hotel."
    Reviewed June 2, 2026
    Return • Los Angeles (LAX) - Boston (BOS)
    LAX - BOS • Direct BOS - LAX • Direct
    AU$783
    AU$638
    per traveller
    found 1 day ago
    Hotel Ivy Boston Common
  • Minibar, desk, laptop workspace, iron/ironing board
    Aug 17 - Aug 21

    The Boston Hotel + Flight

    Brighton
    3 nights
    2.0 star property
    7.4/10 - Good (896 reviews)
    "Very old and unkept hotel."
    Reviewed June 2, 2026
    Return • Los Angeles (LAX) - Boston (BOS)
    LAX - BOS • Direct BOS - LAX • Direct
    AU$1,157
    AU$955
    per traveller
    found 1 day ago
    The Boston Hotel
  • Breakfast area
    Aug 17 - Aug 21

    enVision Hotel Boston Everett + Flight

    Everett
    3 nights
    2.0 star property
    8.4/10 - Very good (1,000 reviews)
    "It has onsite parking. Paid. Close to the airport. Seems to be new construction."
    Reviewed May 31, 2026
    Return • Los Angeles (LAX) - Boston (BOS)
    LAX - BOS • Direct BOS - LAX • Direct
    AU$1,055
    AU$879
    per traveller
    found 1 day ago
    enVision Hotel Boston Everett
  • Front of property
    Aug 17 - Aug 21

    Maverick Suites at 40 Temple St + Flight

    Beacon Hill
    3 nights
    2.0 star property
    7.6/10 - Good (118 reviews)
    "This was. A very nice, clean room. Plenty big enough for one or two people and great location, lots of dining and by the park"
    Reviewed May 28, 2026
    Return • Los Angeles (LAX) - Boston (BOS)
    LAX - BOS • Direct BOS - LAX • Direct
    AU$1,210
    AU$1,011
    per traveller
    found 1 day ago
    Maverick Suites at 40 Temple St
  • Exterior
    Aug 17 - Aug 21

    Maverick Suites at 245 Newbury St + Flight

    Back Bay
    3 nights
    2.0 star property
    8.2/10 - Very good (169 reviews)
    "Did not advertise 6 flights of stairs to get to the room. No elevator, I'm 74 years old ! Provided necessary info just hours before my flight. No tissues, blanket, instructions on how to operate TV. Would not stay again,"
    Reviewed May 20, 2026
    Return • Los Angeles (LAX) - Boston (BOS)
    LAX - BOS • Direct BOS - LAX • Direct
    AU$1,172
    AU$985
    per traveller
    found 1 day ago
    Maverick Suites at 245 Newbury St

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

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

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$419 per night from 7 June to 8 June
AU$419
7 June - 8 June
includes taxes & fees
9.2/10 Wonderful! (4,681 reviews)
"Great location, clean"

Reviewed on 3 June 2026

Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$232 per night from 7 June to 8 June
AU$232
7 June - 8 June
includes taxes & fees
9/10 Wonderful! (2,643 reviews)
"clean room, smell very clean"

Reviewed on 3 June 2026

The Revolution Hotel
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$465 per night from 28 June to 29 June
AU$465
28 June - 29 June
includes taxes & fees
9.6/10 Exceptional! (4,404 reviews)
"This property is perfect! My only complaint is that when I booked it stated that we would have free breakfast and upon arrival they stated that we did not have breakfast included in our stay. Pretty disappointed but it did not take away from the beauty and cleanliness at this hotel"

Reviewed on 1 June 2026

Seaport Hotel Boston
See all 3,935 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?
You can snap up a holiday package to this popular destination 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

Fenway Park

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

Fenway Park
Harvard University

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
Boston Common

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

Activities

Boston Hop-On Hop-Off Trolley Tour

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

AU$80
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

AU$47
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

AU$63
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
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.