Cheswolde Vacations from $271

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to $1,045 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

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.
Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Save 100% on your flight
per person
Aug 13 - Aug 19
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (998 reviews)
They had a pool! The rooms are bigger than most for a good price

Reviewed on Jul 1, 2025

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
Fells Point
Save 100% on your flight
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Baltimore (BWI)
9.4/10 Exceptional! (1,002 reviews)
The location was great, near shoppers and dining and with the breeze from the habor. The pool had next to no shade and ran out of lounges and even towels. We sat at the bar to get some shade and a seat when we got out of the pool. The concierge and desk staff knew very little about the area, attracts or ,unchanged of any thing but they were nice.

Reviewed on Jun 29, 2025

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
9/10 Wonderful! (1,791 reviews)
We stayed at Governor Calvert's House. The location is excellent for walking around downtown and the staff were very friendly and helpful.

Reviewed on Jul 2, 2025

Ocean Glass Inn

Ocean Glass Inn

3.5 out of 5
West Rehoboth
Save 100% on your flight
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Baltimore (BWI)
9.6/10 Exceptional! (1,003 reviews)
2nd time visit and had a great time. Great Location!

Reviewed on Jun 28, 2025

Atlantic Sands Hotel & Conference Center

Atlantic Sands Hotel & Conference Center

3.5 out of 5
North Rehoboth
Save 100% on your flight
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Baltimore (BWI)
8.4/10 Very Good! (1,358 reviews)
Very nice place with great dining within a 5 minute walk. Easy parking.It is dated in the 80s but still very nice

Reviewed on Jul 3, 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

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
3 out of 5
1734 W Nursery Rd, Linthicum Heights, MD
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $91 total per night from Jul 6 to Jul 7
$91 total
Jul 6 - Jul 7
Total includes taxes and fees
8/10 Very Good! (3,739 reviews)
"Always a great experience with hotels.com."

Reviewed on Jul 3, 2025

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
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 Jul 13 to Jul 14
$189 total
Jul 13 - Jul 14
Total includes taxes and fees
8.4/10 Very Good! (2,246 reviews)
"Great service was really appreciated. Super comfy rooms."

Reviewed on Jul 1, 2025

Renaissance Baltimore Harborplace Hotel
Hyatt Place Baltimore Inner Harbor
Hyatt Place Baltimore Inner Harbor
3.5 out of 5
511 S Central Ave, Baltimore, MD
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $175 total per night from Jul 6 to Jul 7
$175 total
Jul 6 - Jul 7
Total includes taxes and fees
8.2/10 Very Good! (2,132 reviews)
"I was very happy with my stay at Hyatt Plac"

Reviewed on Jul 2, 2025

Hyatt Place Baltimore Inner Harbor
See all 1,274 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

$181
per adult
82% 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

$35
per child
72% 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.