Chestnut Hill Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Chestnut Hill

Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
The price is S$259 per night from 20 Dec to 21 Dec
S$259
includes taxes & fees
20 Dec - 21 Dec
9.6/10 Exceptional! (2,591 reviews)
"Excellent property with friendly and welcoming staff. We would definitely stay again!"

Reviewed on 22 Nov,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$253 per night from 8 Dec to 9 Dec
S$253
includes taxes & fees
8 Dec - 9 Dec
8.2/10 Very Good! (3,285 reviews)
"I’ll start with the bad- laying in bed getting ready for bed and a mouse goes running across the floor. I notified front desk and was moved to another room. The good- the staff was friendly, the breakfast buffet was well stocked, and is centrally located to a lot of amenities."

Reviewed on 21 Nov,2024

Hilton Boston Park Plaza
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 S$292 per night from 25 Nov to 26 Nov
S$292
includes taxes & fees
25 Nov - 26 Nov
8.6/10 Excellent! (2,860 reviews)
"I couldn’t be more impressed with the level of service. From the moment I arrived the front desk staff went above and beyond to make me feel welcome. Check-in was smooth and efficient. Throughout my stay, the entire staff always responded and assisted promptly and kindly."

Reviewed on 20 Nov,2024

Omni Parker House
See all 3,186 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 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

Fenway Park showing a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(61 reviews)

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

Fenway Park
Harvard University featuring a city and heritage architecture

Harvard University

4.5/5(102 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

What to do in Chestnut Hill

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

S$97
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Admission Tickets

View Boston Observation Deck Admission Tickets

S$33
Per adult
90% of travellers recommend
View Boston Observation Deck Admission Tickets
Whale-Watching Cruise in Stellwagen Bank Marine Sanctuary

Boston Harbor New England Aquarium Whale-Watching Cruise

S$105
Per adult
86% of travellers recommend
Boston Harbor New England Aquarium Whale-Watching 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.