Beach house holiday rentals in Chesapeake Beach
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Top-rated beach house rentals in Chesapeake Beach
Guests agree: these beach houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake Beach beach house rentals
Beachfront house rentals
Home in Kent Narrows
5.0 out of 5 average rating, 278 reviewsChester Riverfront At Kent Narrows
16–23 Oct
Home in Lusby
4.94 out of 5 average rating, 157 reviewsWaterfront Home on the Chesapeake Bay-Pvt Beach
11–18 Nov
Home in Colonial Beach
4.84 out of 5 average rating, 128 reviews*WATERFRONT BEACH HOUSE PARADISE*
15–22 Oct
Home in Montross
5.0 out of 5 average rating, 120 reviewsBeach Please! River cottage w/private beach & dock
1–8 Oct
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
18–25 Feb
Home in Cambridge
4.95 out of 5 average rating, 100 reviewsPeaceful Historic House Near Water, with Hot Tub!
21–28 Jun
Home in Colonial Beach
4.93 out of 5 average rating, 114 reviews‘Pipe Dream’ - 3BD/2.5BTH - Awesome water view!
3–10 Nov
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
15–22 Nov
Beach house rentals with a pool
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
3–10 Sep
Home in Montross
4.93 out of 5 average rating, 166 reviewsThe Glebe
4–11 Dec
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
19–26 Jun
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
8–15 Jan
Home in Edgewater
4.97 out of 5 average rating, 30 reviewsEntire Beach House with Pool and Hot Tub
31 Oct – 7 Nov
Home in Annapolis
4.95 out of 5 average rating, 41 reviewsNaptown Suite
3–10 Jan
Home in Bozman
5.0 out of 5 average rating, 7 reviewsGrace Creek Cottage
11–18 Aug
Home in Stevensville
5.0 out of 5 average rating, 34 reviewsThe Pool House in Romancoke On The Bay
3–10 Apr
Private beach house rentals
Home in North Beach
4.91 out of 5 average rating, 23 reviewsLarge Bungalow 2 Blocks to Beach
31 May – 7 Jun
Home in North Beach
4.98 out of 5 average rating, 47 reviewsCheerful Two Bedroom Home on the Chesapeake Bay!
6–13 Apr
Home in North Beach
5.0 out of 5 average rating, 95 reviewsWaterfront Home w/ Hot Tub, Pets ok, Peleton
30 Nov – 7 Dec
Home in North Beach
5.0 out of 5 average rating, 8 reviewsOsprey's Perch
3–10 Dec
Home in North Beach
4.98 out of 5 average rating, 95 reviewsHuge Beach Bungalow- Yard, Beach Pass, King Beds
28 Jan – 4 Feb
Home in North Beach
4.98 out of 5 average rating, 52 reviewsThe North Beach Retreat House
22–29 Oct
Home in North Beach
4.88 out of 5 average rating, 8 reviewsCute home 3 beds 2 baths!
5–12 Jan
Home in North Beach
4.95 out of 5 average rating, 41 reviewsChesapeake Bay, Maryland, Beach Front Paradise
27 Apr – 4 May
Destinations to explore
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