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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
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4.96 out of 5 average rating, 121 reviews
Top guest favourite
Home in North Beach
Huge 4 BR Beach House | Fire Pit | Fenced Yard
4 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
4.97 out of 5 average rating, 194 reviews
Top guest favourite
Home in North Beach
Sea La Vie
3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
4.94 out of 5 average rating, 32 reviews
Top guest favourite
Home in North Beach
Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
2 bedrooms, 2 queen beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 185 reviews
Top guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 104 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 470 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, 248 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 224 reviews
Guest favourite
Home in North Beach
The Licorne Beach Cottage
3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Guest suite in Lusby
Waterfront on St. Leonard Creek at Fort Hill
2 bedrooms, 4 beds, 2 bathrooms
14–19 Oct
4.98 out of 5 average rating, 115 reviews
Top guest favourite
Cabin in Hague
Rustic Waterfront Cabin, Firepit, Dock Access
3 bedrooms, 5 beds, 1.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
4.98 out of 5 average rating, 227 reviews
Top guest favourite
Home in Deale
Charming Waterfront 3BR Cottage on Chesapeake Bay
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in West River
Cozy waterview home in West River!
3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Sept
4.97 out of 5 average rating, 167 reviews
Guest favourite
Home in North Beach
Bay Beach House | Screened Porch TV | Walkable
4 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Prince Frederick
Cozy nest for one or two
1 bedroom, 1 queen bed, 1 bathroom
29 Aug – 3 Sept
4.96 out of 5 average rating, 56 reviews
Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 279 reviews
Top guest favourite
Home in Leonardtown
Water's Edge Cottage | Luxury Retreat
2 bedrooms, 2 beds, 2 bathrooms
26–31 Oct
4.99 out of 5 average rating, 139 reviews
Top guest favourite
Tiny home in Solomons
“Cabana by the Bay”-tiny home on a pier!
1 double bed, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 738 reviews