Preston, MD
Travel Guide
Visit Preston
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
$275 nightly
The price is $312 total per night from May 17 to May 18
$312 total
May 17 - May 18
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. ...
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
$603 nightly
The price is $663 total per night from May 10 to May 11
$663 total
May 10 - May 11
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. ...
9.6/10 Exceptional! (381 reviews)
Room was clean, staff were so nice and welcoming. Couldn’t have asked for a nicer view from our room!
Reviewed on May 6, 2026
Best Western Plus Easton Inn & Suites
8708 Alicia Drive Easton MD
$109 nightly
The price is $120 total per night from May 7 to May 8
$120 total
May 7 - May 8
Total with taxes and fees
Book a stay at this business-friendly hotel in Easton. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,005 reviews)
Great stop over as we headed north. Great staff!
Reviewed on May 5, 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.
Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman MD
Stay at this cottage in Wittman. Enjoy free WiFi, private pools, and laundry facilities. Our guests praise the property condition in our reviews. Popular attractions ...
9.8/10 Exceptional! (243 reviews)
Delightful, well-kept cottage.
Reviewed on May 1, 2026
Dollhouse in Central Historic St Michaels
St Michaels MD
Stay at this vacation home in St. Michaels. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Muskrat Park and Clint S. Bradley Park are ...
9.8/10 Exceptional! (59 reviews)
Host was aces….place was great and right in the heart of town
Reviewed on Mar 25, 2026
Waterfront Sunset Bayview: sleeps 6
Chester MD
Stay at this vacation home in Chester. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Bodkin Island and Chesapeake Bay Environmental Center ...
10/10 Exceptional! (26 reviews)
We loved our stay at this gorgeous waterfront property in Chester! The home is clean and bright with many gathering spaces for our group of five. We really enjoyed spending time on the back porch on the comfy couches enjoying the beautiful view or sitting around the large dining table eating and ...
Reviewed on Apr 21, 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.
Popular places to visit
Gilpin's Point Landing
Explore the great outdoors at Gilpin's Point Landing, a lovely green space in Preston.
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- Chesapeake Bay
- Blackwater National Wildlife Refuge
- Harrington Raceway and Casino
- Northern Chesapeake Bay
- Chesapeake Bay Maritime Museum
- Delaware State Fairgrounds
- St. Michaels Winery
- Gerry Boyle Park at Great Marsh
- Harriet Tubman Underground Railroad National Historical Park
- Queenstown Harbor Golf
- Queenstown Premium Outlets
- Choptank River Lighthouse
- Avalon Theatre
- Chesapeake Bay Environmental Center
- Killens Pond State Park
- Harriet Tubman Museum and Educational Center
- Long Wharf Park
- Dorchester County Visitors Center
- Wye Landing
- Talbot County Visitor Center
- Layton's Chance Vineyard and Winery
- Gateway Park
- Bill Burton Fishing Pier State Park
- Kiwanis Park
- Pickering Creek Audubon Center
