Name: St Michaels Inn
Price range: $105 total
Rating: 8

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD

$212 total

per night

Oct 1 - Oct 2

Book a stay at this business-friendly hotel in Chesapeake Beach. Enjoy an outdoor pool, 2 restaurants, and a marina. Our guests praise the helpful staff and ...

8.6/10 Excellent! (1,003 reviews)

"Resort was clean. Thought resort would have microwave in room. Was looking for more adult activities."

Reviewed on Sep 1, 2026

Sonesta ES Suites Annapolis

170 Admiral Cochrane Dr Edgewater MD

$104 total

per night

Sep 21 - Sep 22

Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...

8.8/10 Excellent! (1,010 reviews)

"Me and my partner couldn’t sleep there and my security deposit has not been returned"

Reviewed on Sep 1, 2026

St Michaels Inn

1228 S Talbot Street St. Michaels MD

$105 total

per night

Sep 8 - Sep 9

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! (1,000 reviews)

"There were a couple of minor details with the room but not enough to dissuade me from staying here again. Ginny on the front desk was a joy."

Reviewed on Sep 1, 2026

See all 782 properties in Chesapeake Beach

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.

Breathtaking Waterfront Estate

Neavitt MD

Book a stay at this family-friendly villa in Neavitt. Enjoy private pools, a fitness center, and a garden. Popular attractions Neavitt Park and Royston Island ...

10/10 Exceptional! (76 reviews)

"Nice property right on the water with a convenient kayak lift. The pool area is great with beautiful views. Unfortunately, the pool pump was broken and very loud the first half of our stay but was replaced midweek. Make sure you don’t go over the 12 person max as they have cameras outside and will ..."

Reviewed on Jul 25, 2026

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Shady Side MD

Book a stay at this family-friendly vacation home in Shady Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shadyside Park and Captain ...

9.6/10 Exceptional! (38 reviews)

"This property was in a central location to lots of places. I did think there was going to be a larger beach that you could go to within the community, however it was a very enjoyable stay. The hostess was sweet and the house is adorable."

Reviewed on Aug 9, 2026

Floating 2 bed 2 bath condo stunning views of the bay

Stevensville MD

Stay at this houseboat in Stevensville. Enjoy a beach locale and an in-room coffeemaker. Popular attractions Matapeake State Park and Romancoke Wharf County ...

7.2/10 Good! (9 reviews)

"Hands down the BEST experience I’ve had with VRBO! Kate was prompt with her communication and the boat was absolutely as she described! We are very much looking forward to going back!"

Reviewed on May 21, 2026

See all properties in Chesapeake Beach

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.

Stay near popular Chesapeake Beach attractions

A coastal residential area with houses along the beach and a lighthouse in the distance.

Breezy Point Beach

8.4/10 (61 reviews)

Why not spend a carefree afternoon at Breezy Point Beach during your travels in Chesapeake Beach? Visit the spas in this relaxing area, or simply enjoy its restaurants.

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