Chestnut Hill Vacations

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Find the Best Chestnut Hill Vacation Packages

Chestnut Hill Hotel Deals

citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AED 639 per night from Apr 13 to Apr 14
AED 639
AED 744 total
includes taxes & fees
13 Apr - 14 Apr
9.4/10 Exceptional! (941 reviews)
"Ricky at the front desk was amazing and super helpful! 5 star service!"

Reviewed on 2 April 2025

citizenM Boston Back Bay
Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AED 1,043 per night from May 4 to May 5
AED 1,043
AED 1,233 total
includes taxes & fees
4 May - 5 May
9.4/10 Exceptional! (2,868 reviews)
"Housekeeping and front desk were amazing. When I said my fridge wasn’t working they reset something. When I asked for a fan it was letting my room. Only two negatives is the fridge never worked and the pool closed early at 9. Steven at the front doors was fantastic and so friendly!!!"

Reviewed on 2 April 2025

Seaport Hotel Boston
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
The price is AED 768 per night from Apr 6 to Apr 7
AED 768
AED 894 total
includes taxes & fees
6 Apr - 7 Apr
9/10 Wonderful! (4,969 reviews)
"I enjoyed my 3-night stay most comfortable, clean and accommodating. The only thing missing was hair conditioner. The staff were most helpful and friendly. Dinner at the Inn was delicious! I would stay at Harborside again if I return in the future."

Reviewed on 2 April 2025

Harborside Inn Of Boston
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 vacation package cost?
You can snap up a vacation package to this popular destination on Expedia. However, how much your vacation 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 vacation package, consider traveling 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 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 vacation as a package?
An Expedia vacation 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 vacation package to Chestnut Hill?
If you have your Chestnut Hill vacation 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, favorite 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 accommodations 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 vacation package that brings all your bookings together.

Discover the most popular places to visit in Chestnut Hill