Find Winery Hotels in Eastern Shore, MD

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Eastern Shore Winery Hotels

Top Eastern Shore Winery Hotels

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront

3.0 star property
Downtown Ocean City
9.0 out of 10, Wonderful, (1586)
"The staff was courtesy and helpful. My staff was great and I will stay here again when I return. "
United States
Corey
The price is AED 277
AED 308 total
includes taxes & fees
5 Dec - 6 Dec
Hyatt Place Ocean City / Oceanfront
Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (848)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
The price is AED 375
AED 416 total
includes taxes & fees
23 Nov - 24 Nov
Comfort Inn & Suites Chestertown
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (125)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is AED 460
AED 639 total
includes taxes & fees
1 Dec - 2 Dec
Kent Island Resort
Sundeck
Park Place Hotel

Park Place Hotel

3.0 star property
Downtown Ocean City
9.2 out of 10, Wonderful, (1037)
"Great views and courteous staff."
United States
Michelle L
The price is AED 203
AED 262 total
includes taxes & fees
23 Nov - 24 Nov
Park Place Hotel
Room, 2 Queen Beds, Non Smoking, Oceanfront 1st Floor | In-room safe, desk, laptop workspace, blackout drapes
Courtyard Ocean City Oceanfront

Courtyard Ocean City Oceanfront

3.0 star property
Downtown Ocean City
9.2 out of 10, Wonderful, (996)
"Amazing hotel and staff "
United States
Lorielen
The price is AED 353
AED 391 total
includes taxes & fees
26 Nov - 27 Nov
Courtyard Ocean City Oceanfront
Lobby sitting area
Gillis Grier Bed & Breakfast

Gillis Grier Bed & Breakfast

3.0 star property
Salisbury
10.0 out of 10, Exceptional, (164)
"They have made my stay feel like I am family "
United States
Julia
Gillis Grier Bed & Breakfast
Indoor pool
Comfort Inn Gold Coast

Comfort Inn Gold Coast

2.5 star property
North Ocean City
8.2 out of 10, Very Good, (1002)
"Clean friendly staff in great safe location."
United States
Michael
The price is AED 260
AED 288 total
includes taxes & fees
23 Nov - 24 Nov
Comfort Inn Gold Coast
Exterior
Wingate by Wyndham North East

Wingate by Wyndham North East

2.5 star property
North East
8.0 out of 10, Very Good, (948)
"Room was clean and staff were friendly. They provided a nice breakfast with plenty of options. "
United States
Kathy
The price is AED 426
AED 478 total
includes taxes & fees
30 Nov - 1 Dec
Wingate by Wyndham North East
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom

Port Deposit
10.0 out of 10, Exceptional, (11)
"Great stay in a relaxing community. We loved to be able to walk to places from the house! The hosts were very helpful and easy to communicate with 💙"
United States
Elise E.
The price is AED 489
AED 791 total
includes taxes & fees
3 Dec - 4 Dec
Quarry Landing - Center of Town & River View - 3 Bedroom
Marina
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
Downtown Cambridge
9.6 out of 10, Exceptional, (10)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
The price is AED 514
AED 1,273 total
includes taxes & fees
14 Dec - 15 Dec
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
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.
View all properties

Top Eastern Shore Hotel Reviews

Red Roof Inn Perryville

Red Roof Inn Perryville

10/10 Excellent
"Cleaner modern room and helpful staff."
Andy 1-night trip
Posted 6 days ago
Red Roof Inn Perryville

Explore a world of travel with Expedia