Preston, MD
Travel Guide
Visit Preston
Hyatt Regency Chesapeake Bay
100 Heron Blvd, Cambridge, MD
Fully refundable
The price is $209 total per night from Oct 29 to Oct 30
$209 total
per night
Oct 29 - Oct 30
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! (1,010 reviews)
Very professionally cleaned. Safe.
Reviewed on Oct 15, 2025
St Michaels Inn
1228 S Talbot Street, St. Michaels, MD
The price is $109 total per night from Nov 6 to Nov 7
$109 total
per night
Nov 6 - Nov 7
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! (1,002 reviews)
Basic room, clean and comfortable. Only complaint, it took 15 minutes to get hot water in the shower -- wasted a lot of water waiting. Good TV selection, too.
Reviewed on Oct 17, 2025
Quality Inn & Suites Harrington - Milford
1259 Corn Crib Road, Harrington, DE
The price is $85 total per night from Oct 28 to Oct 29
$85 total
per night
Oct 28 - Oct 29
Book a stay at this business-friendly hotel in Harrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.6/10 Good! (1,014 reviews)
Very good for the price
Reviewed on Oct 23, 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.
Stylish Home on the Choptank River (with Tidal Beach)
Preston
Book a stay at this family-friendly vacation home in Preston. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Gilpin's Point Landing and ...
10/10 Exceptional! (42 reviews)
Used this house for an Eastern Shore golf weekend. Loved the location, right on the Choptank River and was 20-30 minute access to nearby golf courses. House was very clean and welcoming. Kitchen has updated appliances and adequate plates and utensils. Bedrooms were very comfortable. Nice deck for ...
Reviewed on Oct 13, 2025
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)
Ideal location to shops and attractions. Host very easy to reach.
Reviewed on Oct 6, 2025
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Woolford
Book a stay at this beach vacation home in Woolford. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Ragged Island and Spocott Windmill ...
9.8/10 Exceptional! (58 reviews)
We enjoyed our stay in Woolford. The day was filled with fishing, swimming and boating. Thank you again for sharing your property with our family.
Reviewed on Aug 24, 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
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
- Harrington Raceway and Casino
- Blackwater National Wildlife Refuge
- St. Michaels Winery
- Delaware State Fairgrounds
- Choptank River Lighthouse
- Queenstown Premium Outlets
- Chesapeake Bay Maritime Museum
- Harriet Tubman Underground Railroad National Historical Park
- Killens Pond State Park
- Long Wharf Park
- Queenstown Harbor Golf Club
- Chesapeake Bay Environmental Center
- Harriet Tubman Museum and Educational Center
- Gerry Boyle Park at Great Marsh
- Avalon Theatre
- Queenstown Harbor Golf Links
- 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