Chester Vacations from $386
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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!
The Latest Chester vacation packages
Price found within the past 48 hours. Click for updated prices.
Salamander Washington DC
Southwest
Save 100% on your flight
Price was $1,131, price is now $692 per person
$692
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,106 reviews)
My stay was everything I could have imagined. The staff were extremely friendly and attentive. Hospitality was 10 out of 10. The spa services were amazing. Would definitely stay here again.
Reviewed on Jul 2, 2026
Club Quarters Hotel in Washington DC
Downtown Washington D.C.
Save 100% on your flight
Price was $774, price is now $510 per person
$510
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,902 reviews)
Club Quarter was a great place to stay. The staff was helpful and very friendly. We are especially thankful for Melendez who was able to set us up with early arrival. This property is a great location in Washington DC. The White House and the Mall were within walking distance. We would stay there again should we find ourselves in DC again!
Reviewed on Jul 3, 2026
Historic Inns of Annapolis
Historic District
Save 100% on your flight
Price was $786, price is now $518 per person
$518
per person
Aug 12 - Aug 18
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9/10 Wonderful! (1,866 reviews)
Staff was friendly, helpful and wonderful. Room was good, location is great.
Reviewed on Jul 3, 2026
Rachael's Inner Harbor Boutique Inn
Ridgely's Delight
Save 100% on your flight
Price was $778, price is now $523 per person
$523
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
10/10 Exceptional! (5 reviews)
I did not see shops per se. However, Camden yards was a short walk away.
Reviewed on Jun 27, 2026
Stay near popular Chester attractions
What to do in Chester
2 Hour Chesapeake Day Sail on Catamaran Epiphany
$245
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
$160
per adult
Chester Hotel Deals
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $148 total per night from Jul 13 to Jul 14
$148 total
Jul 13 - Jul 14
Total with taxes and fees
9/10 Wonderful! (1,867 reviews)
"Staff was friendly, helpful and wonderful. Room was good, location is great."
Reviewed on Jul 3, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $109 total per night from Jul 5 to Jul 6
$109 total
Jul 5 - Jul 6
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
"The room is clean. Spacious and quiet. Bed is comfortable. We will stay here again."
Reviewed on Jul 3, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
$114 nightly
The price is $130 total per night from Jul 5 to Jul 6
$130 total
Jul 5 - Jul 6
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Excelent"
Reviewed on Jul 2, 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.
Find the Best Chester Vacation Packages
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Baltimore Washington Intl. Thurgood Marshall Airport (BWI) |
Population | 4,200 |
Top Sights | Sandy Point State Park, Sandy Point Beach and Matapeake State Park |
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- Baltimore Maritime Museum
- Annapolis Vacations
- Robert Long House
- Kunta Kinte–Alex Haley Memorial
- Baltimore American Indian Center
- The Colonial Players
- Maryland Vacations
- U.s. Naval Academy Golf Club
- University of Maryland Medical Center
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- Hammond-Harwood House
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- St. Mary's Spiritual Center and Historic Site
- Chesapeake Bay Bridge
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- Hopkins Plaza
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- Queenstown Vacations
- Annapolis City Dock
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- Holocaust Memorial
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- Baltimore City Hall
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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.
