Cheswolde Vacations from $174

Book a Hotel + Flight or Car together to unlock savings

Your Cheswolde Vacation

Say goodbye to the hassle of planning and hello to a Cheswolde vacation package. With your travel details organized before you take off, you can focus on discovering the best of this city, starting with Station North Arts and Entertainment District, which is great for culture, cafes and festivals. If your trip to Cheswolde includes some sightseeing, take in renowned attractions like Baltimore Museum of Art, Washington Monument and Walters Art Museum. Expedia will help you escape the everyday. Tailor your vacation to Cheswolde to suit your style of travel, whatever that may look like.

The Latest Cheswolde Vacation Packages

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

3 out of 5
Price was $230, price is now $174 per person
$174
per person
Nov 18 - Nov 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8/10 Very Good! (3,922 reviews)
It was an quick overnight trip. Its nothing fancy. I just appreciate a clean looking, not run down, an non smelling room. Breakfast is decent...good for what it is.

Reviewed on Sep 17, 2025

Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

3.5 out of 5
Inner Harbor
Save 100% on your flight
Price was $308, price is now $192 per person
$192
per person
Nov 18 - Nov 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (713 reviews)
The only thing missing was a microwave as could not take any leftovers back to room to heat.

Reviewed on Sep 15, 2025

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
Price was $459, price is now $328 per person
$328
per person
Oct 31 - Nov 2
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,853 reviews)
The AC stopped working but was quickly fixed. The coffee was not great-the taste was off. The room is very dark, perhaps more lighting? The beds were comfortable and appreciate the phone charges, steamer in the room.

Reviewed on Sep 14, 2025

Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

4 out of 5
Inner Harbor
Save 100% on your flight
Price was $859, price is now $616 per person
$616
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Baltimore (BWI)
8.6/10 Excellent! (2,318 reviews)
Great location to Inner Harbor Aquarium and waterfront restaurants.

Reviewed on Sep 16, 2025

Holiday Inn Baltimore BWI Airport by IHG

Holiday Inn Baltimore BWI Airport by IHG

3 out of 5
Price was $450, price is now $345 per person
$345
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Baltimore (BWI)
9.2/10 Wonderful! (1,035 reviews)
Very nice and clean establishment

Reviewed on Sep 16, 2025

Where to stay in Cheswolde

Find the best Cheswolde areas and neighborhoods for the activities you enjoy most. Learn more about Cheswolde
Top of the World Observation Level showing a city and a bay or harbor

Inner Harbor

2 out of top 10 points of interest in this area

Historic seaport with post-industrial waterfront redevelopment, the Inner Harbor offers attractions like the National Aquarium and Maryland Science Center. Easily walk to stadiums or catch a water taxi to explore nearby areas.

Find hotels in Inner Harbor

Cheswolde Hotel Deals

Hyatt Regency Baltimore Inner Harbor

Hyatt Regency Baltimore Inner Harbor

4 out of 5
300 Light Street, Baltimore, MD
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $199 total per night from Oct 1 to Oct 2
$199 total
Oct 1 - Oct 2
Total with taxes and fees
8.2/10 Very Good! (1,801 reviews)
"Excellent customer service. Close to shops and restaurants"

Reviewed on Sep 15, 2025

Hyatt Regency Baltimore Inner Harbor
Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

4 out of 5
202 E Pratt St, Baltimore, MD
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $189 total per night from Sep 25 to Sep 26
$189 total
Sep 25 - Sep 26
Total with taxes and fees
8.4/10 Very Good! (2,337 reviews)
"Great location to Inner Harbor Aquarium and waterfront restaurants."

Reviewed on Sep 16, 2025

Renaissance Baltimore Harborplace Hotel
Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
20 W Baltimore St, Baltimore, MD
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $158 total per night from Sep 23 to Sep 24
$158 total
Sep 23 - Sep 24
Total with taxes and fees
8.2/10 Very Good! (2,220 reviews)
"A little outdated but staff is so friendly they fix whatever they can whenever you request"

Reviewed on Sep 16, 2025

Lord Baltimore Hotel
See all 1,272 properties in Cheswolde
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Cheswolde

Oriole Park at Camden Yards

Oriole Park at Camden Yards

4.5/5(495 reviews)

Watch Baltimore’s beloved baseball team play on their home field, located inside a groundbreaking stadium famous for blending classic and modern design elements.

Oriole Park at Camden Yards
Baltimore Inner Harbor Marina

Baltimore Inner Harbor Marina

4.5/5(1,069 reviews)

The transformed former seaport is packed with museums, shops and family attractions and is one of the city’s most photographed areas.

Baltimore Inner Harbor Marina
National Aquarium in Baltimore

National Aquarium in Baltimore

4.5/5(1,044 reviews)

Inner Harbor’s biggest attraction recreates the marine and terrestrial habitats of thousands of animals from many parts of the globe.

National Aquarium in Baltimore

Things to do

Evening view of the roof top deck on the Spirit of Baltimore cruise vessel

Spirit of Baltimore Signature Buffet Dinner Cruise with Live DJ & Bars

$137
per adult
84% of travellers recommend
Spirit of Baltimore Signature Buffet Dinner Cruise with Live DJ & Bars
Glow in the Dark Splatter Paint Experience

Glow in the Dark Splatter Paint Experience

$40
per adult
78% of travellers recommend
Glow in the Dark Splatter Paint Experience
Downtown Baltimore Helicopter Tour

Downtown Baltimore Helicopter Tour

$125
per adult
Downtown Baltimore Helicopter Tour
See all activities in Baltimore
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.