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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
Guest favourite
Home in North Beach
The Licorne Beach Cottage
3 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in North Beach
Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
2 bedrooms, 2 queen beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 184 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 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, 23 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, 31 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
4.96 out of 5 average rating, 83 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, 469 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
Home in North Beach
Emerald Bay
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in West River
Cozy waterview home in West River!
3 bedrooms, 3 beds, 2.5 bathrooms
21–26 Aug
4.97 out of 5 average rating, 166 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
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
Cottage in Deale
"Seas the Bay Cottage" in Deale with Kayaks
3 bedrooms, 6 beds, 3 bathrooms
18–23 Aug
4.97 out of 5 average rating, 94 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, 276 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
Top guest favourite
Home in North Beach
Waterfront- 5-Bedroom House
5 bedrooms, 12 beds, 5.5 bathrooms
26–31 Aug
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
Home in Deale
Hannah’s Hideaway
3 bedrooms, 7 beds, 2 bathrooms
20–25 Oct
4.99 out of 5 average rating, 160 reviews