Chestnut Hill Vacations from $602

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Your Chestnut Hill Vacation

When a getaway to the city is calling, answer it with a Chestnut Hill vacation package. The neighborhood of Downtown Boston, which is great for nightlife, shopping and bars and pubs, makes a wonderful base for your adventures. Love to start exploring your surroundings? Boston College, Agganis Arena and Coolidge Corner Theatre are just a few of the best places to visit during your trip to Chestnut Hill. Your perfect Chestnut Hill vacation is clicks away. Explore airfares, hotels and more on Expedia for a trip that's tailored to suit your travel style.

The Latest Chestnut Hill Vacation Packages

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 28 - Jul 1
Roundtrip non-stop flight included
Atlanta (ATL) 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 6 - Jun 9
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Excellent service and excellent location, wish I could’ve stayed longer than three nights!

Reviewed on Apr 24, 2024

The Boxer

The Boxer

4 out of 5
West End
Save 100% on your flight
per person
Jun 28 - Jul 1
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,014 reviews)
Great staff and a fun property. Would repeat!

Reviewed on Apr 24, 2024

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Jun 28 - Jul 1
Roundtrip non-stop flight included
Atlanta (ATL) 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

YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
Jun 21 - Jun 25
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.2/10 Very Good! (1,617 reviews)
Was great location. Rooms are very small

Reviewed on Apr 22, 2024

Chestnut Hill Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Coolidge Corner Theatre, Larz Anderson Auto Museum and Larz Anderson Park

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 $220 per night from May 26 to May 27
$220
$285 total
includes taxes & fees
May 26 - May 27
9/10 Wonderful! (1,982 reviews)
"Great location!"

Reviewed on Apr 22, 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 $269 per night from Apr 26 to Apr 27
$269
$318 total
includes taxes & fees
Apr 26 - Apr 27
9.4/10 Exceptional! (2,118 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 $161 per night from Apr 28 to Apr 29
$161
$217 total
includes taxes & fees
Apr 28 - Apr 29
9.2/10 Wonderful! (3,367 reviews)
"Hidden gem"

Reviewed on Apr 23, 2024

The Dagny Boston
See all 3,162 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

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Chestnut Hill vacation package cost?
From as low as $602. 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(2,499 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(1,966 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(1,678 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

$79
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

$30
Per adult
100% of travellers recommend
Bewitched Walking Tour of Salem
Image for Freedom Trail: Small Group Tour of Revolutionary Boston

Freedom Trail: Small Group Tour of Revolutionary Boston

$39
Per adult
100% of travellers recommend
Freedom Trail: Small Group Tour of Revolutionary Boston
See all activities in Chestnut Hill

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.