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 Chestnut Hill Vacation Deals

Prices and availability subject to change. Additional terms may apply.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jun. 23 - Jun. 26
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.2/10 Wonderful! (27 reviews)
Very good service. Furniture in all areas and the room is low and petite. Not comfortable. Bedding is comfortable. Food on Long Bar was well prepared. However presentation is pedestrian. Ordered Avacado Toast. Tasty, but arrived on a small plate. No garnish, no fruit etc. overall good stay.

Reviewed on Apr. 8, 2024

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Jun. 23 - Jun. 26
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
i loved my room overlooking the park with gorgeous windows! just lovely.

Reviewed on Apr. 21, 2024

YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
per person
Jul. 4 - Jul. 7
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.2/10 Very Good! (1,617 reviews)
Was great location. Rooms are very small

Reviewed on Apr. 22, 2024

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
per person
Jul. 4 - Jul. 7
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.6/10 Excellent! (1,448 reviews)
Restaurant menu needs further expansion

Reviewed on Apr. 23, 2024

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Jun. 23 - Jun. 26
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (274 reviews)
My husband and I spent one night at The Whitney and were extremely pleased with our stay. The room was lovely and the staff were very nice and helpful. We would absolutely return and recommend it without hesitation.

Reviewed on Mar. 24, 2024

Chestnut Hill Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $322 per night from May 24 to May 25
CA $322
CA $415 total
includes taxes & fees
May 24 - May 25
9/10 Wonderful! (1,977 reviews)
"Great property, king suite was very spacious, peekaboo water views bc they are building in tween the hotel and the harbor now, lots of restaurants, but lacked variety in food selections I feel, great bars and beverages. Staff was excellent, concierge, front desk, room service, bellman services, and ..."

Reviewed on Apr. 21, 2024

Omni Boston Hotel at the Seaport
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 $369 per night from Apr. 26 to Apr. 27
CA $369
CA $436 total
includes taxes & fees
Apr 26 - Apr 27
9.4/10 Exceptional! (2,128 reviews)
"Very clean, amazing staff"

Reviewed on Apr. 21, 2024

Seaport Hotel Boston
The Dagny Boston
The Dagny Boston
4 out of 5
89 Broad Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Apr. 28 to Apr. 29
CA $223
CA $300 total
includes taxes & fees
Apr 28 - Apr 29
9.2/10 Wonderful! (3,350 reviews)
"Beautiful hotel. Top notch in every way. There is so much within walking distance also!"

Reviewed on Apr. 21, 2024

The Dagny Boston
See all 3,174 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chestnut Hill vacation package cost?
From as low as CA $900. Yes, you read that correctly. Our Chestnut Hill vacation 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 vacation 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 vacation 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 neighborhood, 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 favorite Chestnut Hill area. We recommend Cozy 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 vacation?
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 organizing a beach escape in a villa or prefer to stay in a cozy apartment in the city, Expedia can help make it happen.
Can I choose my airline with a Chestnut Hill Expedia vacation 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 vacation package?
We totally get that life can throw you the odd curveball. If you’ve booked a Chestnut Hill vacation 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

Image for Fenway Park

Fenway Park

4.5/5(305 reviews)

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

Fenway Park
Image for Harvard University

Harvard University

4.5/5(279 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
Image for New England Aquarium

New England Aquarium

4.5/5(154 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

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $107
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

CA $41
Per adult
100% of travellers recommend
Bewitched Walking Tour of Salem
Image for Odyssey Boston Premier Elegant Dinner Cruise

Odyssey Boston Premier Elegant Dinner Cruise

CA $239
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
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.