Eastern Shore Vacation Packages
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Top Eastern Shore vacation package deals
Price found within the past 48 hours. Click for updated prices.
5.0-star property
Swanendele Inn at St. Mary's Maryland
9.8/10 Exceptional! (36 reviews)
Jan 11 - Jan 16
5 night stay
Chicago (MDW) to Baltimore (BWI)
Frontier Airlines • Non-stop roundtrip • Coach
Price was $1,838, price is now $1,345 per person
$1,345
per person
found 13 hours ago
Fantastic location. Great breakfast. Very gracious hosts.
Reviewed on Oct 13, 2026
5.0-star property
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
9/10 Wonderful! (1,285 reviews)
Jan 14 - Jan 18
4 night stay
Chicago (ORD) to Baltimore (BWI)
American Airlines • Coach
Baltimore (BWI) to Chicago (ORD)
Frontier Airlines • Coach
Price was $845, price is now $625 per person
$625
per person
found 1 day ago
3.5-star property
Hilton Club The District Washington D.C.
Downtown Washington D.C.
9.4/10 Exceptional! (672 reviews)
Dec 20 - Dec 25
5 night stay
Chicago (ORD) to Baltimore (BWI)
Frontier Airlines • Roundtrip • Coach
Price was $850, price is now $634 per person
$634
per person
found 1 day ago
Shared space with Embassy Suites. Lovely apartment type room and bedroom.
Reviewed on Oct 30, 2026
4.0-star property
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
8.6/10 Excellent! (1,007 reviews)
Dec 3 - Dec 6
3 night stay
Chicago (ORD) to Baltimore (BWI)
Frontier Airlines • Roundtrip • Coach
Price was $564, price is now $431 per person
$431
per person
found 11 hours ago
The room was clean and spacious. The bed was very comfortable. The location was convenient and close to everything we wanted to see.
Reviewed on Nov 1, 2026
Top rated hotels for your Eastern Shore vacation package
Castle in the Sand
3701 Atlantic Avenue Ocean City MD
47.27 mi from city center
At Castle in the Sand, guests have access to an outdoor pool, free WiFi in public areas, and a meeting room. Free parking is available if you drive. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. Other amenities at this beach hotel include laundry facilities, a banquet hall, and an ATM.
Pool
Parking included
Holiday Inn & Suites Ocean City by IHG
1701 Atlantic Avenue Ocean City MD
Free Cancellation
47.46 mi from city center
$90 nightly
The price is $101 total per night
$101 total
Nov 30 - Dec 1
Total with taxes and fees
Holiday Inn & Suites Ocean City by IHG features an indoor pool, a children's pool, and a 24-hour gym. Self parking is available for USD 10 per day. The 24-hour front desk has staff standing by to help with securing valuables, dry cleaning/laundry, and concierge services. Other amenities at this beach hotel include free WiFi in public areas, a hot tub, and conference space.
Pool
Hot Tub
Princess Royale Oceanfront Resort
Oceanfront on 91st Street Ocean City MD
46.66 mi from city center
$101 nightly
The price is $111 total per night
$111 total
Dec 2 - Dec 3
Total with taxes and fees
Guests of Princess Royale Oceanfront Resort enjoy a full-service spa, an indoor pool, and a 24-hour gym. If you drive, put free parking to good use. The 24-hour front desk has staff standing by to help with luggage storage, and answer any questions about the accommodations. Other amenities at this beach hotel include free WiFi in public areas, meeting rooms, and conference space.
Pool
Spa
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.
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