Chestnut Hill Vacations from ￥512,692

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The Latest Chestnut Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
Jul 31 - Aug 7
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (2,304 reviews)
Loved the modern, clean, smoke free environment. Excellent gym, slightly disappointed that there is no pool.

Reviewed on Jun 16, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Jul 31 - Aug 7
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
This was a wonderful overnight stop in Boston. We will be back.

Reviewed on Jun 17, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
Jul 31 - Aug 7
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (275 reviews)
EVERYTHING is thought out. Service is “old world”. Attention to details is magnificent. What’s there not to like.

Reviewed on Jun 9, 2024

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
per person
Jul 31 - Aug 7
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (283 reviews)
This was one of the best hotel experiences I've had. The staff goes above and beyond to make you feel welcomed. From the Tates cookies and sparkling water available, to the water bottles at the end of the night, they really pay attention to small details, making it a great experience. The rooms were clean and roomy. We ended up walking the entire time in Boston since the hotel was at a great location, but if you plan on driving, keep in mind that you have to call ahead of time to access your car. Would definitely stay again!

Reviewed on May 28, 2024

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
per person
Jul 31 - Aug 7
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (263 reviews)
Have tried several Boston hotels over the years but after staying at the Newbury, it will be the only place I stay in Boston from now on.

Reviewed on Jun 16, 2024

Chestnut Hill Hotel Deals

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 ￥28,246 per night from Jun 30 to Jul 1
￥28,246
per night
Jun 30 - Jul 1
8.6/10 Excellent! (1,568 reviews)
A great hotel experience at a fair price.
"I enjoyed my stay at the Revolution Hotel very much. It's located in a nice part of Boston where you can easily access public transportation or walk."

Reviewed on Jun 17, 2024

The Revolution Hotel
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 ￥34,633 per night from Jun 28 to Jun 29
￥34,633
per night
Jun 28 - Jun 29
9/10 Wonderful! (2,206 reviews)
"It was in a great area with shopping, restaurants, the harbor, and walkable to get to some historical sites. We loved the city. It was clean and we always felt safe walking around."

Reviewed on Jun 17, 2024

Omni Boston Hotel at the Seaport
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥28,730 per night from Jul 4 to Jul 5
￥28,730
per night
Jul 4 - Jul 5
8.8/10 Excellent! (2,699 reviews)
"Fascinated Hotel, location is perfect. Service is great. Good Breakfast. Will be back definetly. Thank you."

Reviewed on Jun 15, 2024

Omni Parker House
See all 3,095 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.

Frequently asked questions

How much does a Chestnut Hill vacation package cost?
From as low as ￥512,692. 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 Gillette Stadium

Gillette Stadium

4.5/5(388 reviews)

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium

What to do in Chestnut Hill

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥11,637
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

￥4,419
Per adult
98% 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

￥5,745
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.