Chesapeake Beach Farmstay from CA $104

A harbor with boats docked, a pier, and a row of houses along the water.

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Recommended hotels in Chesapeake Beach

A covered outdoor seating area with tables and chairs, overlooking a marina with boats and a waterway.

1. Rod 'N' Reel Resort

Chesapeake Beach

Theresa

CA $253 total

includes taxes & fees

Oct 6 - Oct 7

2. Family Beach House: Spacious Deck, Grill & Views

Chesapeak beach

Bryan P.

CA $632 total

includes taxes & fees

Sep 8 - Sep 9

A two-story building with a brick facade, a covered entrance, and a bench outside.

3. SureStay by Best Western Prince Frederick

Prince Frederick

Greg

CA $121 total

includes taxes & fees

Sep 16 - Sep 17

A Holiday Inn Express hotel with a brick facade, a central entrance, and a parking lot with several cars.

4. Holiday Inn Express Prince Frederick by IHG

Prince Frederick

Gwen

CA $186 total

includes taxes & fees

Oct 4 - Oct 5

A hotel with a brick facade, a covered entrance, and a sign reading "Springhill Suites."

5. Springhill Suites by Marriott Prince Frederick

Prince Frederick

Joseph

CA $181 total

includes taxes & fees

Sep 27 - Sep 28

A marina with docked boats, a picnic area, and a grassy lawn with a tree.

6. Anchored Inn at Hidden Harbour Marina

Deale

Dale

CA $313 total

includes taxes & fees

Sep 10 - Sep 11

A building with a sign reading "The Inn."

7. Knapps Narrows Marina & Inn

Sherwood

BARBARA

CA $228 total

includes taxes & fees

Sep 7 - Sep 8

A wooden deck with a cushioned seating area, a wicker table, and potted plants.

8. Beachside Oasis with Beach Passes & King Suite by A Haven Away

North Beach

Johanna S.

CA $438 total

includes taxes & fees

Sep 8 - Sep 9

An outdoor bar area with a view of the lake, wooden deck, and metal roof structure.

9. The Tilghman Island Inn

Tilghman

Pamela

CA $311 total

includes taxes & fees

Sep 22 - Sep 23

A building with a covered porch supported by columns, a garage with a parked truck, and a small garden with flowers.

10. St Michaels Inn

St. Michaels

Karen

CA $132 total

includes taxes & fees

Sep 20 - Sep 21

A waterfront property with a covered patio, a dock, and a boat.

11. Wylder Tilghman Island

Tilghman

Angela

CA $366 total

includes taxes & fees

Sep 9 - Sep 10

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

12. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

Penny N.

CA $628 total

includes taxes & fees

Sep 14 - Sep 15

A building with a sign reading "The Inn of the Hills" and a staircase leading to the entrance.

13. Executive Inn And Suites

Upper Marlboro

Frank

CA $104 total

includes taxes & fees

Sep 16 - Sep 17

A Sonesta ES Suites hotel with a brick facade, large windows, and a red awning.

14. Sonesta ES Suites Annapolis

Edgewater

Jake

CA $143 total

includes taxes & fees

Sep 24 - Sep 25

A pool with two Adirondack chairs and a basket of items on the grass.

15. The Inn at Tacaro Estate

Tracys Landing

James

CA $592 total

includes taxes & fees

Sep 7 - Sep 8

16. Historic 1825 Chesapeake Farm Stay

St. Leonard

"This is a must see for yourself!! The owners have thought of every detail from the over the top welcome amenities to extras like offering beach chairs and towels to go explore the local beach! Breakfast was absolutely delicious! She even prepared a to go breakfast when she found out we had to leave out early one morning! We enjoyed home grown fruits and veggies from her garden daily! If you want to step back in time, but still have the comforts of modern day you have to got to visit this place!...

Jessica

CA $182 total

includes taxes & fees

Sep 21 - Sep 22