Chestnut Hill Holidays
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Price found within the past 48 hours. Click for updated prices.
LivAway Suites Portland-Scarborough
S$878
per person
9 Oct - 12 Oct
found 1 day ago
Return direct flight included
Raleigh (RDU) to Boston (BOS)
8/10 Very good! (301 reviews)
Good bed, however missing pots and pans and other appliances that one would use with the full kitchen that was given
Reviewed on 6 Aug, 2026
Candlewood Suites Portland - Scarborough by IHG
S$874
per person
9 Oct - 12 Oct
found 1 day ago
Return direct flight included
Raleigh (RDU) to Boston (BOS)
8.2/10 Very good! (1,001 reviews)
Outside trash bins over flowing, cigarette butts all over ground, dog feces not cleaned up, sidewalk and gazebo area with lose rock where cement had deteriorated. Not a great visual first impression and not addressed quickly.
Nice that rooms have some cookware dishes etc, but would sure be nice to have a small knife to cut instead the big one, Some kitchen shears maybe on a chain screwed into the wall if worried about theft.
More information on what is available to purchase or to borrow as those were great, but I did not happen on some of it until I had stayed several days or already purchased items. Would have been nice to be able to purchase some items in small quantity such as a baggie with 3 or 4 packets of catsup, mustard, mayonnaise, salt, pepper and small tubs of peanut butter and jelly. small containers of cooking oil. more than one kind of laundry detergent (some for sensitive skin) dryer sheets. I hated that I ended up throwing away lots of food items due to not being able to buy small enough amounts for my needs from the grocery store.
Reviewed on 4 Aug, 2026
Where to stay in Chestnut Hill
Find the best Chestnut Hill areas and neighborhoods for the activities you enjoy most. Learn more about Chestnut Hill
Downtown Boston
The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.
Back Bay
1 out of top 10 points of interest in this area
Parisian boulevards and elegant brownstones conjure a truly romantic atmosphere, perfect for strolling and window shopping.
Seaport District
Join excited crowds enjoying harbor-side views, Revolutionary War-era landmarks, as well as superb restaurants and museums along this thriving waterfront.
Beacon Hill
1 out of top 10 points of interest in this area
Take a walk through the charming streets, historic buildings and small-town atmosphere of Boston’s oldest and wealthiest suburbs.
North End
1 out of top 10 points of interest in this area
The ample dining options and captivating waterfront views are just a few popular features of the neighbourhood. Make a stop by Boston Harbor or New England Aquarium while you're visiting, and jump aboard the metro at Aquarium to get around town.
Top hotels in Chestnut Hill
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
S$325
30 Aug - 31 Aug
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
S$203
16 Aug - 17 Aug
includes taxes & fees
9/10 Wonderful! (2,811 reviews)
"Everything is good"
Reviewed on 8 Aug, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
S$402
20 Aug - 21 Aug
includes taxes & fees
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?
You can snap up a holiday package to this popular destination from S$801 on Expedia. However, how much your holiday to Chestnut Hill costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Chestnut Hill?
If you'd like to score a cheap Chestnut Hill holiday package, consider travelling in January, February and November. You'll usually find lower rates on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Chestnut Hill?
The ideal duration of your Chestnut Hill holiday depends on what you'd like to see and do. Typically, a few days to a week will give you plenty of time to hit all the leading attractions and discover some hidden spots along the way.
How to find the best Chestnut Hill package deals?
Start your search for a Chestnut Hill package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Chestnut Hill package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chestnut Hill getaway off to a flying start.
Is it cheaper to book a Chestnut Hill holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and stays separately. Better still, you can tailor your Chestnut Hill trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Chestnut Hill?
If you have your Chestnut Hill holiday dates locked in, book early to snap up some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Chestnut Hill?
- Pick the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Chestnut Hill.
- Work out your budget: Make sure you have enough money to cover everything from dining out and transportation to airfares and activities. Your accommodation will probably be the largest expense during your trip to Chestnut Hill.
- Work out your trip length: Consider how much time you'd like to spend discovering Chestnut Hill. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Chestnut Hill holiday package that brings all your bookings together.
Stay near popular Chestnut Hill attractions
McMullen Museum
6.0/10 (1 review)
This Boston College treasure houses over 5,000 artworks spanning diverse periods and cultures. Explore the serene galleries on Sunday afternoons for free docent-led tours of current exhibitions.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
S$66
per adult
90% of travellers recommend
Boston Duck Boat Sightseeing City Tour with Cruise
S$80
per adult
92% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
S$102
per adult
80% of travellers recommend
* 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.