Hotels with connecting rooms in Eastern Shore, Maryland

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Check prices for these dates

Our top choices for Eastern Shore hotels with connecting rooms

1. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,002 reviews)
"A wonderful stay! Already planning a trip for next year!"
United States
Michelle
The price is P5,990
P6,648 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express Annapolis East-Kent Island by IHG

2. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,005 reviews)
"The staff at the front desk were friendly and helpful."
United States
Billy
The price is P9,110
P12,141 total
includes taxes & fees
Nov 23 - Nov 24
Hyatt Regency Chesapeake Bay

3. Baymont by Wyndham Easton

Baymont by Wyndham Easton
2.5 star property
Easton
7.6 out of 10, Good, (958 reviews)
"Staff who received us was very helpful and respectful. Breakfast was great, rooms are well maintained and clean."
United States
Edwin
The price is P5,170
P5,687 total
includes taxes & fees
Nov 9 - Nov 10
Baymont by Wyndham Easton

4. Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center
2.5 star property
Midtown Ocean City
8.8 out of 10, Excellent, (1,002 reviews)
"Very enjoyable stay. Staff was very warm and welcoming."
United States
Erin
The price is P3,698
P4,141 total
includes taxes & fees
Dec 3 - Dec 4
Hampton Inn & Suites Ocean City/Bayfront-Convention Center

5. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
"Nice location & stay"
United States
Holly
The price is P5,667
P6,290 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Kent Narrows Inn

6. Cambria Hotel Ocean City - Bayfront

Cambria Hotel Ocean City - Bayfront
3.0 star property
Downtown Ocean City
9.0 out of 10, Wonderful, (1,001 reviews)
"Very well maintained staff was super nice and professional higher recommend staying here"
United States
Patricia
The price is P4,267
P5,725 total
includes taxes & fees
Dec 7 - Dec 8
Cambria Hotel Ocean City - Bayfront

7. The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (526 reviews)
"Wonderful place to stay. The staff was beyond helpful. Everything is homemade and nightly s’mores by the fire pit were so much fun! Can not recommend this place enough!"
United States
Dena
The price is P12,547
P15,377 total
includes taxes & fees
Dec 1 - Dec 2
The Wildset

8. Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG
3.0 star property
Downtown Ocean City
9.4 out of 10, Exceptional, (1,468 reviews)
"Wonderful stay with great eats."
United States
Christopher
The price is P5,674
P6,355 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn & Suites Ocean City by IHG

9. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.0 out of 10, Wonderful, (1,008 reviews)
"Plenty of parking! Comfortable beds and pillows. The staff was amazing, kind, helpful and friendly. I would definitely stay there again."
United States
Margaret
The price is P7,503
P8,253 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Plus Easton Inn & Suites

10. Residence Inn by Marriott Ocean City

Residence Inn by Marriott Ocean City
3.0 star property
Midtown Ocean City
9.0 out of 10, Wonderful, (1,002 reviews)
"Clean large room-great view, welcoming staff especially during breakfast-delicious options, last minute stay turned out to be great decision"
United States
Karen
The price is P5,170
P5,790 total
includes taxes & fees
Nov 12 - Nov 13
Residence Inn by Marriott Ocean City
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.