Preston, MD
Travel Guide
Visit Preston
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
$262 nightly
The price is $297 total per night from Apr 20 to Apr 21
$297 total
Apr 20 - Apr 21
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. ...
8.8/10 Excellent! (1,000 reviews)
Great service, room was clean, great food options
Reviewed on Mar 30, 2026
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
$635 nightly
The price is $699 total per night from Apr 19 to Apr 20
$699 total
Apr 19 - Apr 20
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! (379 reviews)
Disappointing. The hotel is lovely but the staff are in training mode and don’t get things quite right. They didn’t tell us there was an Easter brunch so we missed breakfast on Sunday as they had booked out the dining room and everything in town was already full. The food was nice but relatively ...
Reviewed on Apr 5, 2026
St Michaels Inn
1228 S Talbot Street St. Michaels MD
$126 nightly
The price is $138 total per night from Apr 12 to Apr 13
$138 total
Apr 12 - Apr 13
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 ...
8.2/10 Very Good! (1,001 reviews)
The lady that checked us in was so sweet and helpful.
Reviewed on Apr 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.
Stylish Home on the Choptank River (with Tidal Beach)
Preston MD
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! (47 reviews)
A wonderful stay. The house is stylish, comfortable, and perfectly positioned right in front of the river. Waking up to the peaceful water and beautiful scenery made the whole experience feel relaxing and special. The setting is quiet, tranquil, picturesque, and ideal for anyone looking to unwind ...
Reviewed on Mar 16, 2026
Private 2 Acre Waterfront Family Retreat with Pool & Pier
Cambridge MD
Book a stay at this family-friendly vacation home in Cambridge. Enjoy free WiFi, private pools, and a garden. Popular attractions Christ Rock Park and Spocott ...
9.6/10 Exceptional! (89 reviews)
What a wonderful property for big families. We had family members from four states, ranging in age from 3-93, for Thanksgiving. The kitchen was well equipped. We had everything we needed to make four pies, a 22-pound turkey and all the fixings.Our host was pleasant and easy to work with. Very quick ...
Reviewed on Nov 29, 2025
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Saint Michaels MD
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and patios. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina are ...
9.8/10 Exceptional! (200 reviews)
A lovely home just a block from the shops and restaurants on Talbot Street. The rear addition adds generous living space while preserving the charm of the historic house. The screened-in back deck is a great feature for relaxing evenings.Upstairs, the bedroom feels like a second retreat—spacious, ...
Reviewed on Mar 30, 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
- Harrington Raceway and Casino
- Blackwater National Wildlife Refuge
- St. Michaels Winery
- Chesapeake Bay Maritime Museum
- Delaware State Fairgrounds
- Harriet Tubman Underground Railroad National Historical Park
- Queenstown Harbor Golf
- Gerry Boyle Park at Great Marsh
- Northern Chesapeake Bay
- Avalon Theatre
- Choptank River Lighthouse
- Dorchester County Visitors Center
- Queenstown Premium Outlets
- Killens Pond State Park
- Harriet Tubman Museum and Educational Center
- Long Wharf Park
- Chesapeake Bay Environmental Center
- Layton's Chance Vineyard and Winery
- Bill Burton Fishing Pier State Park
- Pickering Creek Audubon Center
- Wye Landing
- St. Michaels Museum
- Talbot County Visitor Center