Visit Oxford
Sandaway Suites & Beach
103 West Strand Road, Oxford, MD
$280 nightly
The price is $308 total per night from Oct 6 to Oct 7
$308 total
Oct 6 - Oct 7
Total with taxes and fees
Stay at this 3-star beach guesthouse in Oxford. Enjoy free WiFi, free parking, and a private beach. Our guests praise the property condition in our reviews. ...
9.2/10 Wonderful! (153 reviews)
"VERY pleasant stay at Sandaway!"
Reviewed on Oct 1, 2025
St Michaels Inn
1228 S Talbot Street, St. Michaels, MD
$92 nightly
The price is $102 total per night from Oct 19 to Oct 20
$102 total
Oct 19 - Oct 20
Total with taxes and fees
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,001 reviews)
"Our room was clean but dated. The water had a bad smell to it."
Reviewed on Sep 30, 2025
Hyatt Regency Chesapeake Bay
100 Heron Blvd, Cambridge, MD
Fully refundable
$233 nightly
The price is $265 total per night from Oct 12 to Oct 13
$265 total
Oct 12 - Oct 13
Total with taxes and fees
Stay at this 4-star 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! (1,012 reviews)
"Indoor and outdoor pools were very clean and nice"
Reviewed on Sep 28, 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.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Saint Michaels
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina ...
9.4/10 Exceptional! (117 reviews)
"Beautifully restored historic home, in a quaint neighborhood, near the water and downtown. We loved it!"
Reviewed on Sep 21, 2025
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Stevensville
Book a stay at this golf vacation home in Stevensville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Matapeake State Park and Bodkin ...
9.8/10 Exceptional! (12 reviews)
"The location was great! And clean beautiful house"
Reviewed on Sep 16, 2025
Floating 2 bed 2 bath condo stunning views of the bay
Stevensville
Stay at this houseboat in Stevensville. Enjoy a beach locale and an in-room coffeemaker. Popular attractions Matapeake State Park and Romancoke Wharf County ...
6.8/10 (5 reviews)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby."
Reviewed on Jun 7, 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
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.
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- Breezy Point Beach
- Blackwater National Wildlife Refuge
- St. Michaels Winery
- Choptank River Lighthouse
- Chesapeake Bay Maritime Museum
- Harriet Tubman Underground Railroad National Historical Park
- Long Wharf Park
- Chesapeake Bay Environmental Center
- Harriet Tubman Museum and Educational Center
- Gerry Boyle Park at Great Marsh
- Avalon Theatre
- Dorchester County Visitors Center
- Wye Landing
- Talbot County Visitor Center
- Martinak State Park
- Bill Burton Fishing Pier State Park
- Layton's Chance Vineyard and Winery
- Pickering Creek Audubon Center
- The Third Haven Friends Meeting House
- St. Michaels Museum