Chestnut Hill Holidays

Photo by Ed Gaffny
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Chestnut Hill Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott West Springfield

Top hotels in Chestnut Hill

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 S$320 per night from 27 May to 28 May
S$320
per night
27 May - 28 May
9/10 Wonderful! (2,056 reviews)
"We were there for a college graduation"

Reviewed on 18 May,2024

Omni Boston Hotel at the Seaport
Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
The price is S$429 per night from 23 May to 24 May
S$429
per night
23 May - 24 May
9.6/10 Exceptional! (2,161 reviews)
"Beautiful room, great staff, walking area very pretty and close to everything."

Reviewed on 19 May,2024

Seaport Hotel Boston
Hilton Boston Park Plaza
Hilton Boston Park Plaza
4 out of 5
50 Park Plaza, Boston, MA
The price is S$351 per night from 27 May to 28 May
S$351
per night
27 May - 28 May
8.4/10 Very Good! (3,330 reviews)
"Nice and convenient"

Reviewed on 21 May,2024

Hilton Boston Park Plaza
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 S$2,079. 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.