Chestnut Hill Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

Photo by Ed Gaffny
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to ฿3,170 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Chestnut Hill

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 ฿6,466 per night from 7 Jul to 8 Jul
฿6,466
per night
7 Jul - 8 Jul
8.8/10 Excellent! (2,691 reviews)
"Elegant building, historical, clean, best and most convenient location."

Reviewed on 12 Jun 2024

Omni Parker House
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 ฿7,936 per night from 6 Jul to 7 Jul
฿7,936
per night
6 Jul - 7 Jul
9/10 Wonderful! (2,174 reviews)
"Very nice stay at the Omni Great hotel and location for meetings and conferences."

Reviewed on 13 Jun 2024

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 ฿6,719 per night from 17 Jun to 18 Jun
฿6,719
per night
17 Jun - 18 Jun
8.6/10 Excellent! (1,541 reviews)
"Great location. Easy to get around on foot. Very clean, polite and helpful staff. Was skeptical at first but shared bathrooms are just fine. Would definitely stay again."

Reviewed on 13 Jun 2024

The Revolution Hotel
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 holiday package cost?
From as low as . Yes, you read that correctly. Our Chestnut Hill holiday 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 holiday 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 holiday 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 neighbourhood, 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 favourite Chestnut Hill area. We recommend Cosy 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 holiday?
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 organising a beach escape in a villa or prefer to stay in a cosy apartment in the city, Expedia can help make it happen.
Can I choose my airline with a Chestnut Hill Expedia holiday 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 holiday package?
We totally get that life can throw you the odd curveball. If you’ve booked a Chestnut Hill holiday 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.

Popular places to visit

What to do in Chestnut Hill

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