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Search results; Over 1,000 homes in Chesapeake Beach

Top guest favourite
Guest suite in Chesapeake Beach
Nice Guest Suite at Chesapeake Bay
1 bedroom, 1 bed, 1 private bathroom
4–9 Jan
,
4.96 out of 5 average rating, 121 reviews
Top guest favourite
Home in North Beach
Sea La Vie
3 bedrooms, 3 beds
23–28 Aug
4.93 out of 5 average rating, 30 reviews
Top guest favourite
Room in Deale
Sunrise Suite Exquisite Bay View Lux/Rom/Spiritual
1 bed
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in North Beach
Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 184 reviews
Top guest favourite
Townhouse in North Beach
Beachside Oasis + Beach Passes | A Haven Away
3 bedrooms, 3 beds
22–27 Aug
4.96 out of 5 average rating, 245 reviews
Top guest favourite
Houseboat in Cambridge
Loveboat, Where Love Meets The Waves.
1 bedroom, 1 bed
17–22 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in North Beach
The Licorne Beach Cottage
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds
25–30 Aug
4.98 out of 5 average rating, 227 reviews
Top guest favourite
Guest suite in North Beach
Charming 1BR Bungalow Guest Suite | Close To Water
1 bedroom, 1 queen bed
28 Sept – 3 Oct
4.96 out of 5 average rating, 56 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 469 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed
17–22 Oct
5.0 out of 5 average rating, 221 reviews
Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
1 bedroom, 2 beds
20–25 Sept
4.99 out of 5 average rating, 274 reviews
Top guest favourite
Room in Stevensville
Rustic & Elegant Private Bed & Bath
1 bed
9–14 Aug
4.98 out of 5 average rating, 304 reviews
Top guest favourite
Flat in Prince Frederick
Cozy nest for one or two
1 bedroom, 1 queen bed
23–28 Aug
4.96 out of 5 average rating, 54 reviews
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed
16–21 Aug
4.99 out of 5 average rating, 359 reviews
Top guest favourite
Tiny home in Solomons
“Cabana by the Bay”-tiny home on a pier!
1 double bed
27 Sept – 2 Oct
4.96 out of 5 average rating, 731 reviews
Top guest favourite
Loft in Lusby
Designer owned Coastal getaway retreat
1 bedroom, 1 queen bed
27 Aug – 1 Sept
5.0 out of 5 average rating, 419 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
16–21 Aug
4.97 out of 5 average rating, 97 reviews
Top guest favourite
Home in North Beach
Modern Bay Home a few blocks from Boardwalk
4 bedrooms, 5 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 16 reviews