How much does a Chestnut Hill vacation package cost?

Offering excellent value package deals from $225 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 2026/2026 from $225

The Latest Chestnut Hill vacation packages

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

Hotel Ulysses, a Member of Design Hotels

Mount Vernon

Save 100% on your flight

$225

per person

Jan 16 - Jan 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9.2/10 Wonderful! (979 reviews)

The hotel itself was good accommodations. Room was clean and well designed. Staff did not accurately communicate how parking worked with the designated lot creating some issues. Lot is isolated about a block away and accessible by a narrow alley.

Reviewed on Dec 3, 2025

EVEN Hotel Rockville - Washington DC Area by IHG

Save 100% on your flight

$299

per person

Feb 11 - Feb 17

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Baltimore (BWI)

8.4/10 Very Good! (1,023 reviews)

Very clean and well kept

Reviewed on Nov 30, 2025

Eurostars Saint Gregory Dupont Circle Georgetown

Downtown Washington D.C.

$240

per person

Jan 9 - Jan 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.6/10 Excellent! (1,008 reviews)

The staff especially Marcus & Noam, the valet. I hope I spelled that correctly.

Reviewed on Nov 20, 2025

Sheraton Baltimore North Hotel

Save 100% on your flight

$270

per person

Jan 16 - Jan 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.2/10 Very Good! (1,001 reviews)

We enjoyed our stay. We were comfortable, had a clean room and the staff were courteous and helpful

Reviewed on Dec 5, 2025

Lord Baltimore Hotel

Downtown Baltimore

Save 100% on your flight

$283

per person

Jan 16 - Jan 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.2/10 Very Good! (2,362 reviews)

I was extremely happy with our stay. Room was clean (you have to request cleaning services if needed) which I preferred as we were only there a short stay. Easy access to anything downtown. 15-20 min walk to M&T Bank Stadium and about 10-15 from the Inner Harbor. The hotel itself is on the older side which I loved. As a history buff this was right up my alley looking at the beautiful Art-Deco elements of the front entrance. The ceiling of the lobby is stunning. My next trip I will definetly be planning to stay here again. As someone who rarely takes the time to write a review, this is worth it.

Reviewed on Dec 4, 2025

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Chestnut Hill Hotel Deals

Embassy Suites by Hilton Baltimore Hunt Valley

213 International Cir Cockeysville MD

Fully refundableReserve now, pay when you stay

$97 nightly

$112 total

Dec 21 - Dec 22

Total with taxes and fees

8.4/10 Very Good! (1,010 reviews)

We stay here every year, for Thanksgiving and Christmas, to see family. The property is well maintained, nice breakfast, nice happy hour with bar and restaurant on property. A small fitness center, and a decent sized pool and hot tub. The staff is always very nice, and the only minor complaint I ...

Reviewed on Nov 28, 2025

Holiday Inn Express Towson - Baltimore North by IHG

1100 Cromwell Bridge Rd Towson MD

Fully refundable

$85 nightly

$98 total

Dec 21 - Dec 22

Total with taxes and fees

8.8/10 Excellent! (1,074 reviews)

Great

Reviewed on Dec 3, 2025

Hilton Garden Inn Baltimore/White Marsh

5015 Campbell Boulevard Baltimore MD

Fully refundableReserve now, pay when you stay

$95 nightly

$110 total

Dec 21 - Dec 22

Total with taxes and fees

7.8/10 Good! (1,013 reviews)

Amazing

Reviewed on Nov 30, 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.