2/5 - Disappointing
Verified traveler
We ate at Doc’s and ordered the rib eye steak, never would I go there again
Visit Oxford
Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
Oxford MD
Stay at this vacation home in Oxford. Enjoy private pools, a garden, and laundry facilities. Popular attractions Oxford Museum and Royston Island are located ...
9.8/10 Exceptional! (20 reviews)
Lovely stay
Wonderful location for a family reunion. Very close to Oxford but felt nicely secluded. House itself was beautiful and charming, and pool was amazing in this hot weather. Would highly recommend
Reviewed on Jun 25, 2025
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
$203 nightly
The price is $231 total per night from Jan 14 to Jan 15
$231 total
Jan 14 - Jan 15
Total with taxes and fees
Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (1,005 reviews)
Great rooms, amenities, staff
Reviewed on Dec 29, 2025
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
$513 nightly
The price is $564 total per night from Jan 15 to Jan 16
$564 total
Jan 15 - Jan 16
Total with taxes and fees
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (373 reviews)
We had a great stay, hotel was very clean and food was great
Reviewed on Jan 3, 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.
Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
Oxford MD
Stay at this vacation home in Oxford. Enjoy private pools, a garden, and laundry facilities. Popular attractions Oxford Museum and Royston Island are located ...
9.8/10 Exceptional! (20 reviews)
Lovely stay
Wonderful location for a family reunion. Very close to Oxford but felt nicely secluded. House itself was beautiful and charming, and pool was amazing in this hot weather. Would highly recommend
Reviewed on Jun 25, 2025
Floating 2 bed 2 bath condo stunning views of the bay
Stevensville MD
Stay at this houseboat in Stevensville. Enjoy a beach locale and an in-room coffeemaker. Popular attractions Matapeake State Park and Romancoke Wharf County ...
7/10 Good! (6 reviews)
Husband & I stayed during the Annapolis boat show to get a feel for what living on a yacht would be like for our year Great Loop adventure and to see what boat features would be important to us when buying. This stay suited us perfectly and Kate’s communication with us with very quick. A minor mechanical ...
Reviewed on Oct 8, 2025
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
Stay at this vacation home in Woolford. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Woods Island and Harriet Tubman Underground Railroad ...
9.4/10 Exceptional! (23 reviews)
Comfortable house near Cambridge for a three day stay. Would stay again!
Reviewed on Dec 14, 2025
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.
Popular places to visit
Oxford Museum
4/5(18 reviews)
You can spend an afternoon browsing the exhibits at Oxford Museum during your trip to Oxford. Stroll along the riverfront or discover the sunsets in this family-friendly area.
Play Ball Dog Park
Play Ball Dog Park is just one of the places to see in Oxford, so why not enjoy the other things to explore during your travels? Wander the riverfront and beaches in the area.
Reviews of Oxford
4.4
Top Destination
3/5 - Okay
Verified traveler
Quiet town
3/5 - Okay
JDK
Minimal shops, handful of dining options compared to St Michaels.
5/5 - Excellent
Verified traveler
We love this little town. Very quaint and residents are so nice.
5/5 - Excellent
Verified traveler
Lovely quiet quaint small town located on estuary of the Chesapeake Bay.
5/5 - Excellent
Verified traveler
It’s a beautiful, charming, old, historic town.
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- Chesapeake Bay
- Blackwater National Wildlife Refuge
- Breezy Point Beach
- Harriet Tubman Underground Railroad National Historical Park
- St. Michaels Winery
- Choptank River Lighthouse
- Gerry Boyle Park at Great Marsh
- Chesapeake Bay Maritime Museum
- Avalon Theatre
- Harriet Tubman Museum and Educational Center
- Dorchester County Visitors Center
- Northern Chesapeake Bay
- Chesapeake Bay Environmental Center
- Wye Landing
- Long Wharf Park
- Bill Burton Fishing Pier State Park
- Talbot County Visitor Center
- Academy of the Arts
- Layton's Chance Vineyard and Winery
- Pickering Creek Audubon Center
- The Third Haven Friends Meeting House
- Harriet Tubman Birthplace Marker
