Holiday rentals in Chesapeake Beach
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Top-rated holiday rentals in Chesapeake Beach
Guests agree: these stays are highly rated for location, cleanliness and more.
Flat in North Beach
4.97 out of 5 average rating, 100 reviewsBayside Oasis of Southern Maryland
1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.
14–21 Mar
Home in North Beach
4.85 out of 5 average rating, 177 reviewsWarm Home Overlooking the Chesapeake Bay
Sitting on the Chesapeake Bay, North Beach is a town where you are so close to things, yet can feel so far away. Only 45 minutes form Washington, DC, you can sit on one of three decks and gaze into the Chesapeake Bay, enjoying all that small town life has to offer. An open plan, with defined spaces, the house is at once cozy (with a fireplace) and spacious for a family. It is great for couples, adventurers, business travelers, and families. This is not a house for large groups or parties.
24 Sep – 1 Oct
Home in Cambridge
5.0 out of 5 average rating, 263 reviews"Happy Campers" Waterfront Apartment!
Come and experience a relaxing getaway at our fully furnished, detached waterfront apartment! Happy Campers is located on the Choptank River, surrounded by acres of pristine land! You will enjoy quiet afternoons, whether you choose to lounge on chairs by the water and birdwatch or take a bike ride down the lane to explore quiet back roads and beautiful country scenery! A short 15 minute drive into the town of Cambridge offers unique boutiques and restaurants, sightseeing and Sailwinds Park!
30 Jan – 6 Feb
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake Beach holiday rentals
Other great holiday rentals in Chesapeake Beach
Guest suite in Lusby
4.99 out of 5 average rating, 299 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
19–26 Mar
Cottage in California
4.97 out of 5 average rating, 190 reviewsCozy Little Cottage
28 Aug – 4 Sep
Cottage in Colonial Beach
4.93 out of 5 average rating, 177 reviewsCozy cottage 3 blocks from beach
13–20 Jan
Home in North Beach
4.86 out of 5 average rating, 58 reviewsLight of North Beach
15–22 Jul
Guest suite in Chesapeake Beach
4.95 out of 5 average rating, 80 reviewsNice Guest Suite at Chesapeake Bay
4–11 Dec
Cottage in North Beach
4.95 out of 5 average rating, 75 reviewsQuiet Coastal Cottage Escape with Water Views
19–26 Mar
Guest suite in North Beach
4.96 out of 5 average rating, 26 reviewsBrand New Guest Suite - Cozy 1 Bedroom Bungalow
18–25 Jun
Flat in Huntingtown
4.87 out of 5 average rating, 15 reviewsPrivate Apartment On An Animal Sanctuary
26 Apr – 3 May
Home in North Beach
4.9 out of 5 average rating, 21 reviewsLarge Bungalow 2 Blocks to Beach
1–8 Aug
Home in Huntingtown
5.0 out of 5 average rating, 7 reviewsBeach House on the Bay
11–18 Apr
Home in North Beach
4.97 out of 5 average rating, 60 reviewsCharming Herrington / Rose Haven Cottage
6–13 Dec
Home in North Beach
5.0 out of 5 average rating, 92 reviewsWaterfront Home w/ Hot Tub, Pets ok, Peleton
31 Oct – 7 Nov
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