How much does a Chestnut Hill vacation package cost?

Offering excellent value package deals from $266 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.

Chestnut Hill Vacation Packages 2025/2026 from $215

The Latest Chestnut Hill vacation packages

Price found within the past 48 hours. Click for updated prices.

Hyatt House BWI Airport Baltimore

Save 100% on your flight

$266

per person

Dec 12 - Dec 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9.4/10 Exceptional! (616 reviews)

2 night stay. Very clean, even the kitchenette area! Quiet, though there were many guests. Didn’t get to try the breakfast but it’s included in the stay. Front desk was pleasant. Check-in was a breeze. The King bed was very comfortable. The updated look was great! As I do not like “ran down” hotels. All in all, I was very satisfied with everything. Would definitely stay again if in the area.

Reviewed on Nov 4, 2025

Courtyard by Marriott Baltimore Downtown/Inner Harbor

Harbor East

Save 100% on your flight

$317

per person

Dec 22 - Dec 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9/10 Wonderful! (1,006 reviews)

We were in an ajoining room suite on one side only. The bolt lock to the ajoining room was not locked nd could not be locked. Ajoining room was noisy until 11pm when we confronted them Bed mattress was very uncomfortable (hard and lumpy)

Reviewed on Oct 26, 2025

The Inn at Henderson's Wharf, an Ascend Collection Hotel

Fells Point

Save 100% on your flight

$448

per person

Dec 22 - Dec 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9.2/10 Wonderful! (740 reviews)

The bed was extremely comfortable and the room was cozy, and the front desk staff were helpful and friendly!

Reviewed on Nov 6, 2025

Historic Inns of Annapolis

Historic District

Save 100% on your flight

$345

per person

Dec 31 - Jan 4

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

9/10 Wonderful! (1,848 reviews)

The front desk staff provided exceptional customer service throughout my stay. The room was spotless and provided me a quiet space to work.

Reviewed on Nov 3, 2025

Pendry Baltimore

Fells Point

Save 100% on your flight

$755

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

9.4/10 Exceptional! (1,004 reviews)

This review is more so about the management staff Nichola. There was a mix up in dates and I had booked this hotel at a non refundable rate via Expedia. I called Expedia to see if they could consult with the manager at the Pendry for a cancellation. When Expedia contacted the Pendry they spoke with Nichola and she declined the request for cancellation. I kept my reservation based on this decision and arrived at the property the day that was booked. My stay with my family was remarkable, thanks to Brittany at the front desk. She is truly a gem with a positive attitude and demonstrates wonderful customer service. When I received my final bill at check out there were additional charges on the bill that I did not apply to my bill because the room was paid for prior to arrival. Brittany got the manager involved, Nichola, and instead of seeing the error and correcting it, Nichola went back and forth with me and blamed Expedia. There was clearly an error within the billing due to Expedia and the Pendry, but as a customer that has nothing to do with me. As a manager, she should’ve saw the error, corrected the issue with me (the customer) and handled the problem with Expedia on the back end. I didn’t appreciate the lack of accountability and lack of customer service approach Nichola took. The Pendry is a lovely hotel, the overall customer service did not match to me.

Reviewed on Oct 27, 2025

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Chestnut Hill Hotel Deals

Hilton Garden Inn Baltimore/White Marsh

5015 Campbell Boulevard, Baltimore, MD

Fully refundableReserve now, pay when you stay

$92 nightly

$106 total

Nov 16 - Nov 17

Total with taxes and fees

7.8/10 Good! (1,012 reviews)

Great I love it

Reviewed on Nov 2, 2025

Comfort Inn Baltimore East Towson

8801 Loch Raven Blvd, Parkville, MD

5.8/10 (1,009 reviews)

Not required

Reviewed on Oct 14, 2025

Get rates

Holiday Inn Express Towson - Baltimore North by IHG

1100 Cromwell Bridge Rd, Towson, MD

Fully refundable

$92 nightly

$106 total

Nov 23 - Nov 24

Total with taxes and fees

8.8/10 Excellent! (1,060 reviews)

The room smelled a little smoky like someone had smoked in it or in hallway.

Reviewed on Nov 3, 2025

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.