Crumpton
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Fairfield Inn & Suites by Marriott Middletown
411 MERRIMAC AVENUE Middletown DE
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Sep 20 to Sep 21
CA $165
CA $184 total
Sep 20 - Sep 21
includes taxes & fees
Stay at this hotel in Middletown. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
The price is CA $150 per night from Sep 10 to Sep 11
CA $150
CA $171 total
Sep 10 - Sep 11
includes taxes & fees
Book a stay at this beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
8/10 Very good! (105 reviews)
"Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and ..."
Reviewed on Aug 30, 2026
Holiday Inn Express & Suites Middletown by IHG
315 Auto Park Dr Middletown DE
The price is CA $140 per night from Sep 13 to Sep 14
CA $140
CA $156 total
Sep 13 - Sep 14
includes taxes & fees
Stay at this hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.2/10 Wonderful! (723 reviews)
"Clean and conveniently located."
Reviewed on Aug 28, 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.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Rock Hall MD
Book a stay at this family-friendly villa in Rock Hall. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Rock Hall Harbor and The Mainstay ...
10/10 Exceptional! (48 reviews)
"This is a beautiful place! Spacious and very accommodating for large groups. We had 19 there and just tons of room. The grandkids loved the pool. The back yard faces the bay and provides a magnificant view for sunsets. Moreover, we were on the patio between the pool and breezeway when the feels like ..."
Reviewed on Aug 8, 2026
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Earleville MD
Book a stay at this beach apartment in Earleville. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Turkey Point Light and Elk Neck State Park ...
10/10 Exceptional! (69 reviews)
"The stay was very enjoyable. The hosts were friendly and thoughtful. Sunsets were great too. The members of the community we met were very friendly. The Grille up the street has excellent food. We did hike the 6.5 miles of trails at Bohemia River State Park."
Reviewed on Aug 13, 2026
First Floor Studio Apartment in Historic Chestertown
Chestertown MD
Book a stay at this golf apartment in Chestertown. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Wilmer Park and Sumner Hall are ...
9.8/10 Exceptional! (124 reviews)
"Very nice, clean apartment in an excellent setting and location. It was perfect for our getaway to the eastern shore area. Certainly would recommend it and would stay there again."
Reviewed on Aug 28, 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.
