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
19–26 Oct
Home in Chincoteague Island
4.95 out of 5 average rating, 316 reviewsTranquil Shores - Nature Inspired Relaxation!
14–21 Nov
Home in St. Leonard
4.91 out of 5 average rating, 162 reviewsCozy Cottage on the Chesapeake Bay
19–26 Apr
Home in Montross
5.0 out of 5 average rating, 120 reviewsBeach Please! River cottage w/private beach & dock
1–8 Oct
Home in Lusby
4.94 out of 5 average rating, 157 reviewsWaterfront Home on the Chesapeake Bay-Pvt Beach
8–15 Jan
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
20–27 Mar
Home in Cambridge
4.95 out of 5 average rating, 100 reviewsPeaceful Historic House Near Water, with Hot Tub!
13–20 Oct
Home in Mineral
4.99 out of 5 average rating, 119 reviewsLakefront with 120' Beach, Views, Wifi @ Lake Anna
20–27 Dec
Beach house rentals with a pool
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
8–15 Mar
Home in Montross
4.93 out of 5 average rating, 166 reviewsThe Glebe
4–11 Dec
Home in Chincoteague
4.94 out of 5 average rating, 294 reviewsSeas the Day Getaway~Pool ~near Waterfront Park
9–16 Feb
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
5–12 Sep
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
9–16 Sep
Home in Bozman
5.0 out of 5 average rating, 6 reviewsGrace Creek Cottage
2–9 Jan
Home in Sherwood
5.0 out of 5 average rating, 51 reviewsChesapeake Mansion-heated pool 30acre waterfront
28 Jan – 4 Feb
Private beach house rentals
Home in Saint Michaels
4.9 out of 5 average rating, 156 reviewsSmall Historic House Downtown St Michaels
19–26 Jan
Home in North Beach
4.97 out of 5 average rating, 60 reviewsCharming Herrington / Rose Haven Cottage
29 Sep – 6 Oct
Home in North Beach
4.91 out of 5 average rating, 23 reviewsLarge Bungalow 2 Blocks to Beach
10–17 Sep
Home in North Beach
4.98 out of 5 average rating, 47 reviewsCheerful Two Bedroom Home on the Chesapeake Bay!
30 May – 6 Jun
Home in Shady Side
4.97 out of 5 average rating, 65 reviewsCanary Pointe-A popular getaway for 2!
18–25 Mar
Home in North Beach
5.0 out of 5 average rating, 94 reviewsWaterfront Home w/ Hot Tub, Pets ok, Peleton
22–29 Jan
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, 52 reviewsThe North Beach Retreat House
13–20 May
Destinations to explore
- Baltimore Holiday rentals
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