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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
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
Home in North Beach
Modern Bay Home a few blocks from Boardwalk
4 bedrooms, 5 beds, 4.5 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 18 reviews
Top 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
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
Home in North Beach
Emerald Bay
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 24 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
Cottage in North Beach
The Blue Crab Beach House - Free beach passes
2 bedrooms, 2 beds, 2 bathrooms
6–11 Sept
4.95 out of 5 average rating, 84 reviews
Guest favourite
Home in Shady Side
Waterfront Coastal Retreat w/ Beach Access
3 bedrooms, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 7 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
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
Room in Deale
Sunrise Suite Exquisite Bay View Lux/Rom/Spiritual
1 bed, 1 bathroom
30 Sept – 5 Oct
5.0 out of 5 average rating, 11 reviews
Superhost
Home in West River
Cozy Bayside Retreat
2 bedrooms, 4 beds, 1.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 4 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 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, 240 reviews
Top guest favourite
Home in Huntingtown
Grand Tudor Home w/ Saltwater Pool & Hot Tub
5 bedrooms, 6 beds, 3.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 6 reviews