Chestnut Hill Vacation Packages

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Your Chestnut Hill Vacation

With plenty of highlights as well as hidden gems, this city is best experienced with a Chestnut Hill vacation 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 organizing your perfect vacation to Chestnut Hill today.

Top Holiday Package Deals in Chestnut Hill

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,171, price is now CA $829 per person
CA $829
per person
Jul 23 - Jul 26
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!

Reviewed on Sep 20, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,040, price is now CA $1,299 per person
CA $1,299
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Service both at the hotel and restaurants was the one of the best experiences I’ve had

Reviewed on May 2, 2026

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was CA $2,338, price is now CA $1,555 per person
CA $1,555
per person
Jun 19 - Jun 24
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Boston (BOS)
9.6/10 Exceptional! (66 reviews)
It's a relatively nea property, so very clean. Rooms are good. Location is amazing as it overlooks the HBS campus. The staff can do better by providing ready solutions to their customers when required and coordinate better with each other. Thos can enhance the experience for sure!

Reviewed on May 6, 2026

Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was CA $1,528, price is now CA $1,047 per person
CA $1,047
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Boston (BOS)
8.4/10 Very Good! (1,430 reviews)
I was only here because I had an early flight out of Boston the next morning. I arrived way past standard check in time (3-4 pm), and the staff were very communicative, friendly and understanding. The room did the trick for just an overnight. Comfortable beds with comfortable pillows. Loved the bathroom. Loved the lighting. Only thing to note for future travelers that may be “negative”: The pictures make the room look much bigger than it is, like the size of a standard hotel room. It is about 1/4 of the size of a normal hotel room. At least this was the case for my room.

Reviewed on May 6, 2026

Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Price was CA $1,671, price is now CA $1,185 per person
CA $1,185
per person
Jul 10 - Jul 13
found 2 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
8/10 Very Good! (268 reviews)
After reading some terrible reviews, I was initially worried but my stay ended up being great. I had an ocean front king room with a balcony, full ocean view. The room was clean with minor signs of wear and tear. The indoor pool and hot tub were open, even in April and it was nice to have options for food on site. I enjoyed this as a quiet getaway in April. Not sure what the other rooms are like and what the vibe is like during the busy season.

Reviewed on May 6, 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

Downtown Boston

4.5/5(197 area reviews)

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.

Find hotels in Downtown Boston

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 CA $234 per night from May 10 to May 11
CA $234
CA $319 total
May 10 - May 11
includes taxes & fees
9.6/10 Exceptional! (4,288 reviews)
Beautiful hotel

Reviewed on May 6, 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 CA $217 per night from May 10 to May 11
CA $217
CA $308 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (4,635 reviews)
Super clean hotel! Great water pressure! Comfy bed! Staff could be friendlier and smile more. Kestra needs help! Get more servers! Reduce rates for small room like 7777

Reviewed on May 6, 2026

Omni Boston Hotel at the Seaport
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $241 per night from May 10 to May 11
CA $241
CA $337 total
May 10 - May 11
includes taxes & fees
9.4/10 Exceptional! (5,043 reviews)
The hotel staff provided excellent service. I forgot a shirt in the room when I checked out, and the manager notified me via email to request to have it sent to my home. The location is perfect. Easy to walk to Boston Commons, Boston Gardens, subway station, and historic sites. Will return to this ...

Reviewed on May 6, 2026

The Godfrey Hotel Boston
See all 3,988 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.
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Frequently asked questions

How much does a Chestnut Hill vacation package cost?
You can pick up a vacation package to this top destination from CA $829 on Expedia. But how much your vacation to Chestnut Hill costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Chestnut Hill?
You can usually find lower prices and better availability in January, February and November. Browse our cheap Chestnut Hill vacation packages and you could land some excellent off-season deals.
How many days is enough for Chestnut Hill?
With about 3 days, you'll have plenty of time to visit popular neighbourhoods such as Coolidge Corner South Side and Griggs Park during your Chestnut Hill vacation. Remember to also add Frederick Law Olmsted National Historic Site and GASP to your sightseeing list. Looking for more adventures? Consider venturing outside of Chestnut Hill on day trips and tours.
How to find the best Chestnut Hill package deals?
Begin your search for a Chestnut Hill package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Chestnut Hill package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chestnut Hill escape off to a flying start.
Is it cheaper to book a Chestnut Hill vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays individually. Better still, you can customize your Chestnut Hill trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Chestnut Hill?
If you're considering a spur-of-the-moment Chestnut Hill adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Chestnut Hill?

  1. Choose when to travel: Check your diary and pack your bags. Your favourite time of year and the type of activities available will also help you decide when to escape to Chestnut Hill.
  2. Set your budget: Factor in expenses such as flights, meals and transportation when working out how much to save for your trip to Chestnut Hill. Then, select a hotel that suits your budget, whether that's a wallet-friendly stay or a deluxe retreat.
  3. Decide your trip length: Think about how much time you want to spend exploring Chestnut Hill. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your airfare and accommodations: After you've settled on your trip dates and duration, book the right Chestnut Hill vacation package for you.

Discover the most popular places to visit in Chestnut Hill

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Boston College

4/5(15 reviews)

Take a campus tour or just explore the area of Boston College, during your trip to Boston. Stroll along the riverfront or attend a sporting event in this vibrant area.

Boston College
Fenway Park

Fenway Park

4.5/5(310 reviews)

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

Fenway Park
Harvard University

Harvard University

4.5/5(284 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

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $79
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $116
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% 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.