Chestnut Hill Vacations from $183

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The Latest Chestnut Hill vacation packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Hotel Baltimore Inner Harbor
Renaissance Baltimore Harborplace Hotel
Baltimore executive Furnished rentals
Hilton Washington DC Capitol Hill
Lord Baltimore Hotel
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Chestnut Hill Hotel Deals

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard Baltimore MD
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $122 total per night from Jan 18 to Jan 19
$122 total
Jan 18 - Jan 19
Total with taxes and fees
7.8/10 Good! (1,017 reviews)
All was well

Reviewed on Jan 4, 2026

Hilton Garden Inn Baltimore/White Marsh
Holiday Inn Express Towson - Baltimore North by IHG

Holiday Inn Express Towson - Baltimore North by IHG

2.5 out of 5
1100 Cromwell Bridge Rd Towson MD
Fully refundable
$98 nightly
The price is $113 total per night from Jan 18 to Jan 19
$113 total
Jan 18 - Jan 19
Total with taxes and fees
8.8/10 Excellent! (1,090 reviews)
Great front desk lady was awesome very good !!

Reviewed on Jan 9, 2026

Holiday Inn Express Towson - Baltimore North by IHG
Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

2 out of 5
1240 Chesapeke Overlook Parkway Perryville MD
Fully refundable
$199 nightly
The price is $223 total per night from Jan 15 to Jan 16
$223 total
Jan 15 - Jan 16
Total with taxes and fees
8.6/10 Excellent! (162 reviews)
Like it

Reviewed on Jan 8, 2026

Great Wolf Lodge Perryville
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.

Find the Best Chestnut Hill Vacation Packages

Things to do near Chestnut Hill

Chestnut Hill, Maryland, is perfect for outdoor and family-themed vacations, offering a mix of educational experiences, shopping centers, and golf opportunities. Visitors can enjoy outdoor adventures, explore vacation itineraries, and participate in day tours. Whether you're looking for a relaxing getaway or an active adventure, Chestnut Hill has something for everyone to enjoy.

Shopping

For a delightful shopping experience in Chestnut Hill, visit the Harford Mall, located 6 miles away, offering a variety of entertainment and family-friendly vibes. If you're up for a drive, check out the White Marsh Mall and Towson Town Center, both known for their vibrant atmosphere and diverse shops.

Recreation

Experience the thrill at Ripken Stadium, just 10 miles away, where sports energy abounds. Enjoy the serene outdoors at Bulle Rock Golf Course, 13 miles from Chestnut Hill, perfect for golf enthusiasts. For a cultural escape, visit Milburn Stone Theater, 21 miles away, offering a delightful mix of entertainment and family fun.

Adventure

At Guppy Gulch Quarry, 8 miles from Chestnut Hill, enjoy thrilling water slides and relaxing pools for a fun-filled family day. Experience the excitement of navigating through Maize Quest Fun Park's maze, located 13 miles away, perfect for family bonding and adventure seekers alike.

Nightlife

In Chestnut Hill, Maryland, enjoy a charming nightlife with cozy bars and restaurants. Explore local favorites like the Chestnut Hill Brewery for craft beers or join friends at The Green Turtle for lively sports and music. The atmosphere is friendly and inviting, perfect for a relaxed evening out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Chestnut Hill

Chestnut Hill, Maryland, is an ideal destination for outdoor and family vacations, offering a mix of urban parks, historic colleges, and nature reserves. Visitors can explore the Chestnut Hill Reservoir and enjoy various attractions that provide adventure and a taste of local culture. With its scenic landscapes and engaging experiences, Chestnut Hill promises a memorable getaway for travelers seeking both relaxation and exploration.

  • Harford Community College: Located 5 miles from Chestnut Hill, this modern college offers a vibrant atmosphere with a mix of academic and community events. Visitors can enjoy its beautiful campus, attend cultural events, and engage with local art and educational programs.
  • Liriodendron Mansion: Also 5 miles away, this historic mansion serves as a charming venue for events and conferences. Its elegant architecture and serene gardens provide a perfect backdrop for gatherings, making it a unique place to experience local history and culture.
  • Rocks State Park: Just 4 miles from Chestnut Hill, this national park is a haven for outdoor enthusiasts. With breathtaking views, hiking trails, and opportunities for rock climbing, it’s the ideal spot for adventure seekers and nature lovers alike.

Tips to save on your trip to Chestnut Hill

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Chestnut Hill during the low season (December to February) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Chestnut Hill Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
40ºF
Max Temp Summer
80ºF

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Frequently asked questions

How much does a Chestnut Hill vacation package cost?
Offering excellent value package deals from $183 on Expedia, you'll be thrilled with how little a vacation to Chestnut Hill costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chestnut Hill?
December, January and February are great times to search for cheap Chestnut Hill vacation packages. Opting to travel in quieter months means you'll typically find better prices on hotels and flights.
How many days is enough for Chestnut Hill?
With a well-planned schedule, you can easily tick off the most popular Chestnut Hill attractions in a handful of days. But if you prefer to explore off the beaten track or go on day tours, consider booking your Chestnut Hill vacation for longer.
How to find the best Chestnut Hill package deals?
Use Expedia's handy filters to find some tempting Chestnut Hill package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Chestnut Hill package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book 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 retreat by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Chestnut Hill?
If you're planning an impromptu Chestnut Hill trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Chestnut Hill vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Chestnut Hill trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.