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.
Guest suite in Lusby
4.99 out of 5 average rating, 299 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own completely private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is beautiful Solomon’s island. Boaters welcome!
25 Feb – 4 Mar
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.
4–11 Nov
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.
11–18 Dec
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
Cottage in California
4.97 out of 5 average rating, 190 reviewsCozy Little Cottage
13–20 Nov
Home in Shady Side
5.0 out of 5 average rating, 113 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
18–25 Mar
Cottage in Colonial Beach
4.93 out of 5 average rating, 176 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
17–24 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
14–21 Apr
Home in North Beach
4.97 out of 5 average rating, 60 reviewsCharming Herrington / Rose Haven Cottage
23–30 Sep
Bungalow in North Beach
4.88 out of 5 average rating, 64 reviewsBayside Bungalow: Cozy North Beach Getaway
12–19 Nov
Home in North Beach
4.98 out of 5 average rating, 46 reviewsCheerful Two Bedroom Home on the Chesapeake Bay!
17–24 Oct
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