Chestnut Hill Vacations from ￥365,882
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Chestnut Hill Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Kimpton Hotel Monaco Baltimore Inner Harbor by IHG
Downtown Baltimore
￥368,728
per person
Oct 10 - Oct 16
found 12 hours ago
Roundtrip flight included
Tokyo (TYO) to Baltimore (BWI)
8.8/10 Excellent! (442 reviews)
Great place to stay. Clean room, bathroom it was great vibe. Only recommendation is to have a mini bar/ snacks.
Reviewed on Aug 24, 2026
Find the Best Chestnut Hill Vacation Packages
Chestnut Hill Hotel Deals
River Edge Inn
30 Colonial Ave Colonial Beach VA
Fully refundableReserve now, pay when you stay
￥13,990
￥17,164 total
Sep 20 - Sep 21
includes taxes & fees
8.2/10 Very Good! (514 reviews)
"Bathrooms was dirty and had hair in them, fridge hadn’t been empty and had soda spilt in and sticky and the other room had mold on the pillows"
Reviewed on Aug 27, 2026
Best Western La Plata Inn
6900 Crain Highway La Plata MD
Fully refundableReserve now, pay when you stay
￥11,507
￥13,004 total
Aug 31 - Sep 1
includes taxes & fees
Red Roof Inn Dahlgren - Naval Base
4661 James Madison Pkwy King George VA
Fully refundableReserve now, pay when you stay
￥11,944
￥13,174 total
Aug 31 - Sep 1
includes taxes & fees
7.2/10 Good! (696 reviews)
"There are only terrible words to say so I'm not saying anymore."
Reviewed on Aug 23, 2026
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.
What to do in Chestnut Hill
Fredericksburg Ghost Tour Discover Our Haunted Streets
￥4,629
per adult
100% of travellers recommend
Frequently asked questions
How much does a Chestnut Hill vacation package cost?
You'll find cheap prices from ￥365,882 on Expedia for your Chestnut Hill getaway. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Chestnut Hill costs.
What are the cheapest months to go to Chestnut Hill?
If you're looking to book a cheap Chestnut Hill vacation package, consider visiting in January, February and March. You'll typically find better rates on hotels and airfares during these months — perfect for a budget-friendly break.
How many days is enough for Chestnut Hill?
The ideal length of your Chestnut Hill vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to go to all the main sights and explore some hidden gems along the way.
How to find the best Chestnut Hill package deals?
Finding a cheap Chestnut Hill package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most affordable Chestnut Hill package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Chestnut Hill vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Chestnut Hill vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Chestnut Hill?
Enjoy incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Chestnut Hill escape.
How to plan a trip to Chestnut Hill?
- Choose your dates: The things you'd like to do in Chestnut Hill and your preferred season will help you decide when to travel.
- Plan your budget wisely: On top of the price of your stay, you should consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Chestnut Hill.
- Decide your trip length: Consider how much time you want to spend discovering Chestnut Hill. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
- Combine your accommodations and airfare: Once you've settled on your dates and duration, lock in the right Chestnut Hill vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
