Chester Vacation Packages
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Your Chester Vacation
Reserve a Chester vacation package and get set to experience the best of this city. Consider basing yourself in the neighborhood of Kent Narrows, which is good for cycling, views and nature. If your trip to Chester includes some sightseeing, check out renowned attractions like Chesapeake Bay Environmental Center, Eastern Neck National Wildlife Refuge and Love Point State Park. Stop daydreaming and start doing. Browse the multitude of options on Expedia today and finally put your Chester vacation plans into gear!
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Price was CA $1,840, price is now CA $1,237 per person
CA $1,237
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Baltimore (BWI)
9/10 Wonderful! (1,157 reviews)
Really nice hotel and near the main turist attractions
Reviewed on Apr 1, 2026
YOTEL Washington DC
Northwest
Price was CA $2,922, price is now CA $2,102 per person
CA $2,102
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Washington (DCA)
8.2/10 Very Good! (2,335 reviews)
I wish I got a room that had a view but it’s okay, only stayed one day and the cleanliness of the bathroom was top tier and that’s my biggest issue when it comes down to getting hotels. the bed was so comfy I slept like a baby! I had a decent night, I would stay again. The only downside to it is that parking is expensive. 50$ a night, and there was a 100$ deposit but I got it the same day I checked out. I wish the rooftop was open as well. either way I still had a wonderful stay!
Reviewed on Apr 8, 2026
Residence Inn Alexandria Old Town South at Carlyle
Eisenhower East
Price was CA $1,511, price is now CA $1,089 per person
CA $1,089
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Washington (DCA)
8.8/10 Excellent! (1,002 reviews)
Tip—park at lot next to Eisenhower metro station 8 daily vs 40 daily at hotel.5 min walk Place is close to metro and free dash buses
Reviewed on Apr 7, 2026
Placemakr Buzzard Point
Southwest
Price was CA $2,625, price is now CA $1,893 per person
CA $1,893
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Washington (DCA)
9.2/10 Wonderful! (164 reviews)
The room was very nice and clean. It made me want to stay longer. Love the view especially floor to ceiling windows. Couldn’t have asked for better accommodations. We will be returning to this location.
Reviewed on Mar 30, 2026
Chester Hotel Deals
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester MD
10/10 Exceptional! (126 reviews)
Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly..
Reviewed on Sep 14, 2025
Graduate by Hilton Annapolis
126 West St Annapolis MD
The price is CA $284 per night from Apr 19 to Apr 20
CA $284
CA $323 total
Apr 19 - Apr 20
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
It was the perfect location for our activities
Reviewed on Apr 5, 2026
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.
Discover the most popular places to visit in Chester
Chesapeake Exploration Center
Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
