Chestnut Hill Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Top Chestnut Hill Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
CA $1,243
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
8.8/10 Excellent! (1,005 reviews)
This property needs to be updated. The air con was running like a turbo engine with a lot of noise. The thermostat of the AC was antiquated and should sit in an antique store!! The shower was not shutting off and was leaking all the time. the quality of the pull on couch was very poor. The hotel staff was good, however, could use people who could understand and speak better English. Could not understand them completely
Reviewed on Aug 24, 2026
InterContinental Washington D.C. - The Wharf by IHG
The Wharf
CA $1,644
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
9.4/10 Exceptional! (1,215 reviews)
It was amazing. We missed some items in the bathroom and there were only one cup for coffee or tea. But all the rest was assome.
Reviewed on Aug 23, 2026
The River Inn
Northwest
CA $1,382
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
9.4/10 Exceptional! (2,084 reviews)
We like to stay here when we have the entire family because we can stay in 1 room. There’s some things I forgot like how small the beds are, lighting in rooms is poor, ac runs constantly bc it’s an older place. But the location is amazing and again we can all fit into 1 suite and stay together so the trade off out weigh the negatives
Reviewed on Aug 24, 2026
Ready to book your vacation to Chestnut Hill?
Chestnut Hill Hotel Deals
Great Wolf Lodge Perryville
1240 Chesapeke Overlook Parkway Perryville MD
CA $252
CA $282 total
Aug 31 - Sep 1
includes taxes & fees
Embassy Suites by Hilton Baltimore Hunt Valley
213 International Cir Cockeysville MD
Fully refundableReserve now, pay when you stay
CA $168
CA $194 total
Sep 6 - Sep 7
includes taxes & fees
8.6/10 Excellent! (1,014 reviews)
"Love the quality of internet connection. Love the happy hour."
Reviewed on Aug 24, 2026
Comfort Inn Towson - Baltimore North
8801 Loch Raven Blvd Parkville MD
Fully refundable
CA $92
CA $107 total
Sep 21 - Sep 22
includes taxes & fees
5.8/10 (1,025 reviews)
"It was horrible experience. We had to change hotels due to mice in the room."
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.
Frequently asked questions
How much does a Chestnut Hill vacation package cost?
You'll find cheap prices from CA $1,243 on Expedia for your Chestnut Hill escape. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to Chestnut Hill costs.
What are the cheapest months to go to Chestnut Hill?
You can typically find reduced prices and greater availability in January, February and November. Check out our cheap Chestnut Hill vacation packages and you could score some great off-season discounts.
How many days is enough for Chestnut Hill?
The ideal duration for your Chestnut Hill vacation depends on what you'd like to do and see. Typically, a few days to a week will give you enough time to visit all the major attractions and discover some hidden spots along the way.
How to find the best Chestnut Hill package deals?
Use Expedia's filter tool to help you find some of the best Chestnut Hill package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Chestnut Hill package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Chestnut Hill vacation as a package?
You can enjoy significant savings on your Chestnut Hill getaway by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to browse the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chestnut Hill?
Score amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Chestnut Hill escape.
How to plan a trip to Chestnut Hill?
- Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Chestnut Hill.
- Plan your budget wisely: Besides the cost of your stay, you should consider other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Chestnut Hill.
- Set the duration of your trip: Start by making a list of all the sights and activities you'd like to experience in Chestnut Hill. Then, estimate how long you'll need at each, as well as any travel time.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Chestnut Hill vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
