filters

Search results; Over 1,000 homes in Chesapeake Beach

Top guest favourite
Cottage in Deale
"Seas the Bay Cottage" in Deale with Kayaks
3 bedrooms, 6 beds, 3 bathrooms
28 Sept – 3 Oct
4.97 out of 5 average rating, 95 reviews
Top guest favourite
Home in North Beach
Bayfront Home with Amazing Rooftop Deck!
5 bedrooms, 10 beds, 4.5 bathrooms
22–27 Sept
4.98 out of 5 average rating, 133 reviews
Top guest favourite
Home in Huntingtown
Grand Tudor Home w/ Saltwater Pool & Hot Tub
5 bedrooms, 6 beds, 3.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in North Beach
Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
2 bedrooms, 2 queen beds, 2.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 188 reviews
Top guest favourite
Cottage in North Beach
Waterfront Cottage Near Herrington and North Beach
2 bedrooms, 3 beds, 2 bathrooms
10–15 Nov
4.97 out of 5 average rating, 381 reviews
Top guest favourite
Home in North Beach
Waterfront- 5-Bedroom House
5 bedrooms, 12 beds, 5.5 bathrooms
23–28 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest suite in Lusby
Waterfront on St. Leonard Creek at Fort Hill
2 bedrooms, 4 beds, 2 bathrooms
27 Oct – 1 Nov
4.98 out of 5 average rating, 118 reviews
Top guest favourite
Home in Cambridge
Gorgeous, Waterfront Home Is Perfect for Families!
7 bedrooms, 12 beds, 5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 140 reviews
Home in North Beach
Bay watch Oasis Awaits!
3 bedrooms, 1 king bed, 2.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest house in Owings
Relaxing retreat on the river.
1 king bed, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in North Beach
Comfy King Bed Home, walk to dinner & beach!
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Home in North Beach
Huge 4 BR Beach House | Fire Pit | Fenced Yard
4 bedrooms, 4 beds, 3 bathrooms
18–23 Oct
4.97 out of 5 average rating, 196 reviews
Top guest favourite
Home in Lusby
Cove Point Beach Home 1 &1/2 blocks to Beach
3 bedrooms, 4 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 244 reviews
Top guest favourite
Home in Tilghman Island
Panoramic water views
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Oct
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Home in Hollywood
Waterfront Home: Osprey Getaway
4 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Townhouse in North Beach
Beachside Oasis + Beach Passes | A Haven Away
3 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
4.96 out of 5 average rating, 251 reviews
Top guest favourite
Home in Shady Side
Peaceful Coastal Escape | Water Views + Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Bozman
The Cottage at Broad Creek
1 bedroom, 1 bed, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 53 reviews