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.
3.5-star property
Hilton Club The District Washington D.C.
Downtown Washington D.C.
9.4/10 Exceptional! (672 reviews)
Dec 17 - Dec 22
5 night stay
Orlando (MCO) to Baltimore (BWI)
Frontier Airlines • Roundtrip • Coach
Price was $801, price is now $551 per person
$551
per person
found 1 day ago
Beautiful property & very friendly staff!
Reviewed on Nov 2, 2026
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 17 hours ago
Fantastic location. Great breakfast. Very gracious hosts.
Reviewed on Oct 13, 2026
3.5-star property
Airlie Hotel
8.6/10 Excellent! (367 reviews)
Dec 9 - Dec 13
4 night stay
Orlando (MCO) to Baltimore (BWI)
Frontier Airlines • Roundtrip • Coach
Price was $616, price is now $461 per person
$461
per person
found 3 hours ago
Check in was painful. We waited for 30 minutes while the nice desk person waited for someone who knew how yo process our check in. We had booked the stay thru Expedia.
Reviewed on Oct 27, 2026
5.0-star property
The Watergate Hotel
Northwest
8.8/10 Excellent! (1,185 reviews)
Dec 8 - Dec 11
3 night stay
Orlando (MCO) to Baltimore (BWI)
Frontier Airlines • Roundtrip • Coach
Price was $828, price is now $626 per person
$626
per person
found 23 hours ago
Staff was super friendly.
Reviewed on Oct 31, 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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