Cheswolde Vacations from $281

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
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.

Hotel Arlington

Maywood

Save 100% on your flight

$281

per person

Oct 24 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8/10 Very Good! (29 reviews)

The hotel is very bare bones when it comes to extras and amenities, but for the price the staff was friendly and the room was clean. A/C is a little loud but I prefer that so it didn’t bother me but I could see how it would bother someone who needs super quiet to sleep.

Reviewed on Sep 20, 2026

Comfort Inn & Suites Baltimore Inner Harbor

Downtown Baltimore

Save 100% on your flight

$353

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

5.2/10 (1,000 reviews)

The room was nice and clean, very comfortable and meet our expectations. Evening staff not so friendly but the morning staff was really nice and welcoming. The only thing I didn’t like was swapping out the towels. You have to bring your dirty towels down and swap for clean towels. I feel like housekeeping should bring these to you upon request

Reviewed on Sep 21, 2026

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.

Save 100% on your flight

$825

per person

Nov 24 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9/10 Wonderful! (1,249 reviews)

Club Quarters Hotel White House, Washington DC

Downtown Washington D.C.

Save 100% on your flight

$510

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9/10 Wonderful! (2,044 reviews)

I had a wonderful stay at Club Quarter. I would definitely come again and recommend it to family and friends.

Reviewed on Sep 21, 2026

Convention Center PH Free indoor parking

Downtown Baltimore

Save 100% on your flight

$435

per person

Nov 23 - Nov 28

found 1 day ago

Roundtrip flight included

Miami (MIA) to Baltimore (BWI)

3.4/10 (3 reviews)

Property managers never returned calls. Never returned messages or provided check-in instructions. When we arrived at night with my son, they still did not answer and then, after 25 calls, they answered and said it was canceled that morning. We booked one month out and we were confirmed. I travel all the time. Worst experience of my life with any business, especially a “hospitality” business.

Reviewed on Jul 19, 2026

Where to stay in Cheswolde

Find the best Cheswolde areas and neighborhoods for the activities you enjoy most. Learn more about Cheswolde

A cityscape with a river, modern buildings, and a bridge.

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.

A grand library with multiple floors of bookshelves, ornate railings, and a central aisle.

Downtown Baltimore

1 out of top 10 points of interest in this area

Central business district meets historic charm in this neighborhood, with attractions like the National Aquarium, Maryland Science Center, and Lexington Market. Enjoy diverse dining, nightlife, and easy access to public transportation.

A narrow alleyway flanked by brick buildings with ivy, leading to a body of water.

Fells Point

Historic waterfront neighborhood with a maritime vibe, Fell's Point boasts a high concentration of pubs and restaurants. Explore diverse architecture, unique shops, and reach it easily via water taxi or a short walk from the Inner Harbor.

A large stately building with a prominent central tower, surrounded by lush green lawns and trees.

Timonium

If you're looking for some top things to see and do in Timonium and surrounding area, you can visit Towson Town Center and Greenspring Station.

Middle East

Though Middle East might not have many top sights, you can venture to the surrounding area to see attractions like Baltimore Inner Harbor Marina and Jewish Museum of Maryland.

Cheswolde Hotel Deals

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

1734 W Nursery Rd Linthicum Heights MD

Fully refundableReserve now, pay when you stay

$73 nightly

$83 total

Sep 27 - Sep 28

Total with taxes and fees

8.2/10 Very Good! (4,774 reviews)

"The room was very clean. Love having the mini-fridge. The bed was really comfortable. The location was convenient to places to eat."

Reviewed on Sep 21, 2026

Renaissance Baltimore Harborplace Hotel

202 E Pratt St Baltimore MD

Fully refundableReserve now, pay when you stay

$188 nightly

$221 total

Oct 8 - Oct 9

Total with taxes and fees

Hyatt Regency Baltimore Inner Harbor

300 Light Street Baltimore MD

Fully refundableReserve now, pay when you stay

$189 nightly

$222 total

Sep 22 - Sep 23

Total with taxes and fees

8.4/10 Very Good! (2,019 reviews)

"Bar was crowded"

Reviewed on Sep 21, 2026

See all 1,290 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.