Chestnut Hill Vacations from $309

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The Latest Chestnut Hill vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Save 100% on your flight
Price was $551, price is now $309 per person
$309
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,006 reviews)
Staff was polite and kind

Reviewed on Aug 23, 2025

Hampton Inn & Suites Baltimore Inner Harbor

Hampton Inn & Suites Baltimore Inner Harbor

2.5 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $607, price is now $397 per person
$397
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,003 reviews)
Expensive and inefficient vallet service

Reviewed on Aug 22, 2025

Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

3.5 out of 5
Inner Harbor
Save 100% on your flight
Price was $643, price is now $425 per person
$425
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (680 reviews)
No drains for water on balconies

Reviewed on Aug 20, 2025

Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

4 out of 5
Inner Harbor
Save 100% on your flight
Price was $645, price is now $431 per person
$431
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (2,299 reviews)
The hotel was magnificent

Reviewed on Aug 22, 2025

Hotel Indigo Baltimore Downtown by IHG

Hotel Indigo Baltimore Downtown by IHG

4 out of 5
Mount Vernon
Save 100% on your flight
Price was $617, price is now $423 per person
$423
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (1,000 reviews)
Nice hotel- stylish and very centrally located. Half mile walk to a string of really good restaurants. Also some beautiful landmarks and architecture along the way. Parking garage across the street so don’t bother with valet. Hotel room was not as clean as I would have liked- we found a cat toy on the floor along with bits of what we think was cat food in various areas of the floor, hard to see since both were brown but an indication the room wasn’t thoroughly vacuumed/ mopped. Also things like the door to the bathroom and other furnishing had fingerprints etc.- just didn’t look cleaned.

Reviewed on Aug 23, 2025

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Chestnut Hill Hotel Deals

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
$117 nightly
The price is $135 total per night from Aug 26 to Aug 27
$135 total
Aug 26 - Aug 27
Total with taxes and fees
8.8/10 Excellent! (1,041 reviews)
"The staff was friendly."

Reviewed on Aug 20, 2025

Holiday Inn Express Towson - Baltimore North by IHG
Comfort Inn Baltimore East Towson

Comfort Inn Baltimore East Towson

2.5 out of 5
8801 Loch Raven Blvd, Parkville, MD
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $82 total per night from Aug 31 to Sep 1
$82 total
Aug 31 - Sep 1
Total with taxes and fees
5.8/10 (1,001 reviews)
"It was great for me and my wife"

Reviewed on Jul 22, 2025

Comfort Inn Baltimore East Towson
Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
903 Dulaney Valley Rd, Towson, MD
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $127 total per night from Aug 31 to Sep 1
$127 total
Aug 31 - Sep 1
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
"It was nice and clean"

Reviewed on Aug 19, 2025

Sheraton Baltimore North Hotel
See all 285 properties in Chestnut Hill
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.

Things to do near Chestnut Hill

Chestnut Hill, Maryland, is perfect for family-friendly and outdoor vacations, offering a variety of activities. Visitors can explore shopping centers and malls, take in scenic hiking trails, and enjoy outdoor adventures. Whether you're looking for vacation tours, day trips, or detailed itineraries, Chestnut Hill has something for everyone to create memorable experiences.

Shopping

For shopping in Chestnut Hill, visit Harford Mall, located 6 miles away, offering a variety of entertainment and family-friendly shops. If you're up for a drive, check out White Marsh Mall, 18 miles away, and Towson Town Center, 20 miles away, both featuring vibrant shopping experiences.

Recreation

At Ripken Stadium, immerse yourself in the energetic atmosphere of sports events while enjoying recreational activities. Bulle Rock Golf Course offers picturesque views and outdoor fun for golf enthusiasts. Milburn Stone Theater invites you to experience captivating performances, perfect for a romantic night out or family entertainment.

Adventure

At Guppy Gulch Quarry, 8 miles from Chestnut Hill, enjoy thrilling water slides and relaxing pools perfect for families. Maize Quest Fun Park, 13 miles away, offers a fun-filled maze experience for all ages. For climbing enthusiasts, Earth Treks Climbing Center, located 19 miles away, provides an exhilarating outdoor climbing adventure.

Nightlife

Chestnut Hill's nightlife features a vibrant mix of bars and live music. Visit The Dogfish Head Craft Brewery on Market Street for unique brews. For a lively atmosphere, check out The Chestnut Grill, where you can enjoy cocktails and local bands performing throughout the week.

*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 perfect for family-friendly outdoor vacations, offering a blend of nature reserves, historic colleges, and urban parks. Explore top attractions like the Chestnut Hill Reservoir and enjoy a range of activities that cater to adventure seekers and families alike. Whether you're interested in scenic nature walks or learning about local history, Chestnut Hill has something for everyone to enjoy.

  • Harford Community College: Experience the vibrant atmosphere of this modern college located 5 miles from Chestnut Hill. With its contemporary facilities and various events, it offers a lively environment that reflects the pulse of community education and engagement.
  • Liriodendron Mansion: Situated 5 miles away, this historic mansion serves as a unique conference venue. Its elegant architecture and serene surroundings provide a perfect backdrop for events, blending business with charm and sophistication.
  • Rocks State Park: Just 4 miles from Chestnut Hill, this national park is a haven for outdoor enthusiasts. With its breathtaking scenery, hiking trails, and adventurous activities, it’s an ideal spot for those seeking nature and excitement.

Tips to save on your trip to Chestnut Hill

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chestnut Hill.
  • 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.

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Frequently asked questions

How much does a Chestnut Hill vacation package cost?
Offering excellent value package deals from $309 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.