Chestnut Hill Holidays

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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$301 per night from 18 Feb to 19 Feb
S$301
includes taxes & fees
18 Feb - 19 Feb
9.6/10 Exceptional! (2,789 reviews)
Nice overnight at the Seaport Hotel
"There was a big group checking in so the concierge checked us in. He was great. Friendly and quick. We had a nice room on the 17th floor with a view of the harbor. Room was clean and confortable. Large screen TV. We had dinner at Mortons right next door. Nice Valentines get away."

Reviewed on 14 Feb,2025

Seaport Hotel Boston
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
The price is S$170 per night from 23 Feb to 24 Feb
S$170
includes taxes & fees
23 Feb - 24 Feb
9/10 Wonderful! (4,752 reviews)
"The vibe"

Reviewed on 15 Feb,2025

Harborside Inn Of Boston
Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is S$349 per night from 23 Feb to 24 Feb
S$349
includes taxes & fees
23 Feb - 24 Feb
9/10 Wonderful! (3,250 reviews)
"Overall no complaints. Would be nice if an ironing board was provided in place of just the steamer"

Reviewed on 17 Feb,2025

Omni Boston Hotel at the Seaport
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 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

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. 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.