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Choose from 412 Preston Hotel Deals

Hyatt Regency Chesapeake Bay
Hyatt Regency Chesapeake Bay
4 out of 5
100 Heron Blvd, Cambridge, MD
  • 44 min drive from Gilpin's Point Landing
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! (1,005 reviews)
"We were truly impressed by the beauty of the resort. While it may be pricey for just one night, it was unquestionably the best choice to celebrate my mother's birthday alongside my brother and his family. The kids had a fantastic time enjoying all the amenities. We will be returning soon without ..."

Reviewed on May 27, 2025

Hyatt Regency Chesapeake Bay
St Michaels Inn
St Michaels Inn
2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
  • 25 min drive from Gilpin's Point Landing
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)
"Property early 50s"

Reviewed on May 27, 2025

St Michaels Inn
Inn at Perry Cabin
Inn at Perry Cabin
5 out of 5
308 Watkins Ln, St. Michaels, MD
  • 25 min drive from Gilpin's Point Landing
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! (345 reviews)
"The Junior Suite was excellent. Transportation to and from local businesses was wonderful."

Reviewed on May 25, 2025

Inn at Perry Cabin
Quality Inn & Suites Harrington - Milford
Quality Inn & Suites Harrington - Milford
2.5 out of 5
1259 Corn Crib Road, Harrington, DE
  • 28 min drive from Gilpin's Point Landing
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! (999 reviews)
"Good"

Reviewed on May 29, 2025

Quality Inn & Suites Harrington - Milford
Days Inn & Suites by Wyndham Seaford
Days Inn & Suites by Wyndham Seaford
2 out of 5
23450 Sussex Highway, Seaford, DE
  • 36 min drive from Gilpin's Point Landing
Book a stay at this business-friendly hotel in Seaford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our ...
6.6/10 (731 reviews)
"Room was a fairly large room. Lots of space for 4 travelers. Rooms where very clean"

Reviewed on May 27, 2025

Days Inn & Suites by Wyndham Seaford
Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG
Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG
2.5 out of 5
17271 S Dupont Hwy, Harrington, DE
  • 29 min drive from Gilpin's Point Landing
Book a stay at this business-friendly hotel in Harrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,002 reviews)
"Can't think of a bad thing to say."

Reviewed on May 25, 2025

Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG
Quality Inn
Quality Inn
2.5 out of 5
101 Vfw Ave, Grasonville, MD
  • 32 min drive from Gilpin's Point Landing
Stay at this hotel in Grasonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.8/10 Good! (759 reviews)
"Communicate with reception is quite a pleasure."

Reviewed on May 21, 2025

Quality Inn
Best Western Plus Easton Inn & Suites
Best Western Plus Easton Inn & Suites
2.5 out of 5
8708 Alicia Drive, Easton, MD
  • 13 min drive from Gilpin's Point Landing
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! (1,002 reviews)
"Very nice place staff at the front desk was very friendly. Room was clean and nice. Would definitely recommend!"

Reviewed on May 29, 2025

Best Western Plus Easton Inn & Suites
The Wildset
The Wildset
2.5 out of 5
209 N Talbot St, St. Michaels, MD
  • 25 min drive from Gilpin's Point Landing
Stay at this hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.6/10 Exceptional! (316 reviews)
"We really enjoyed our stay. I will say the rooms were not quiet. You could hear people leaving and coming in, and dogs barking."

Reviewed on May 27, 2025

The Wildset
Days Inn & Suites by Wyndham Cambridge
Days Inn & Suites by Wyndham Cambridge
2.5 out of 5
2917 Ocean Gateway, Rt.50 East, Cambridge, MD
  • 45 min drive from Gilpin's Point Landing
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6.6/10 (1,005 reviews)
My stay at days inn
"My room was ok I had a problem with the bad smell in the bathroom overall the staff was nice and friendly"

Reviewed on May 25, 2025

Days Inn & Suites by Wyndham Cambridge
The Tidewater Inn
The Tidewater Inn
3 out of 5
101 E Dover St, Easton, MD
  • 15 min drive from Gilpin's Point Landing
Stay at this 3-star spa hotel in Easton. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (797 reviews)
"Great staff. Great property."

Reviewed on May 30, 2025

The Tidewater Inn
Wylder Tilghman Island
Wylder Tilghman Island
2 out of 5
21551 Chesapeake Access Drive, Tilghman, MD
  • 39 min drive from Gilpin's Point Landing
Stay at this hotel in Tilghman. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tilghman Watermen’s Museum and Talbot County Library Tilghman ...
8.8/10 Excellent! (37 reviews)
"Great spot for a weekend with my daughter and grandson. The heated pool was terrific and so was the food!"

Reviewed on May 30, 2025

Wylder Tilghman Island
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.

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