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.
Hotel Hive
Northwest
Price was CA $1,237, price is now CA $868 per person
CA $868
per person
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.2/10 Wonderful! (1,461 reviews)
Small and efficient rooms. Great location. Helpful, friendly staff. Perfect for my visit.
Reviewed on May 30, 2026
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Price was CA $1,970, price is now CA $1,211 per person
CA $1,211
per person
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (1,185 reviews)
Location was ideal. Staff and service were top notch. Will return for sure.
Reviewed on May 31, 2026
The River Inn
Northwest
Price was CA $1,321, price is now CA $952 per person
CA $952
per person
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,954 reviews)
We really enjoyed our stay at this hotel. The rooms were spacious and well-equipped with kitchen appliances, which made our stay very comfortable. What I loved most was that pets are welcome with no extra fees, which is a huge plus. Everyone on the staff was friendly, welcoming, and helpful throughout our stay. I would definitely come back to this hotel the next time I’m in Washington, DC. Highly recommended!
Reviewed on May 30, 2026
Fairmont Washington, D.C., Georgetown
Northwest
Price was CA $1,881, price is now CA $1,381 per person
CA $1,381
per person
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,002 reviews)
Great location and very nice lobby and bar area. The rooms are spacious and very clean.
Reviewed on May 28, 2026
Hotel Madera
Downtown Washington D.C.
Price was CA $1,348, price is now CA $1,005 per person
CA $1,005
per person
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.2/10 Wonderful! (1,009 reviews)
Spacious room. Great location - near restaurants and the Metro. Wonderful, helpful staff. Great place for a fun trip to DC.
Reviewed on May 30, 2026
Chester Hotel Deals
Waterfront Sunset Bayview: sleeps 6
Chester MD
10/10 Exceptional! (28 reviews)
"Very nice host and beautiful modern house! Close to town and had a dock right there to sit out on and enjoy a cup or coffee! Only complaint was one shower never got hot or warm but we just used one and it was fine"
Reviewed on May 22, 2026
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester MD
10/10 Exceptional! (128 reviews)
"Super wonderful stay!! Double thumbs up on all counts!"
Reviewed on May 26, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from Jun 8 to Jun 9
CA $160
CA $229 total
Jun 8 - Jun 9
includes taxes & fees
9/10 Wonderful! (1,853 reviews)
"Great location with views all the way to the Bay Bridge from some rooms. Comfortable and spacious room."
Reviewed on May 30, 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.
What to do in Chester
2 Hour Chesapeake Day Sail on Catamaran Epiphany
CA $335
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
CA $219
per adult
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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.
