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 favourite

Flat in North Beach

4.97 out of 5 average rating, 100 reviews

Bayside 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

€ 136 per night
Superhost

Home in North Beach

4.85 out of 5 average rating, 177 reviews

Warm 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

€ 284 per night
Guest favourite

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

€ 155 per night

Popular amenities for Chesapeake Beach holiday rentals

Stay near Chesapeake Beach's top sights

Rod 'N' Reel Restaurant51 locals recommend
Traders Seafood Steak & Ale17 locals recommend
Abners Crab House23 locals recommend
Neptune's Seafood Pub29 locals recommend
Mamma Lucia By the Bay6 locals recommend
Bayfront Park9 locals recommend

Other great holiday rentals in Chesapeake Beach

Guest favourite

Guest suite in Lusby

4.99 out of 5 average rating, 299 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

19–26 Mar

€ 137 per night
Guest favourite

Cottage in California

4.97 out of 5 average rating, 190 reviews

Cozy Little Cottage

28 Aug – 4 Sep

€ 105 per night
Guest favourite

Cottage in Colonial Beach

4.93 out of 5 average rating, 177 reviews

Cozy cottage 3 blocks from beach

13–20 Jan

€ 129 per night
Guest favourite

Home in North Beach

4.86 out of 5 average rating, 58 reviews

Light of North Beach

15–22 Jul

€ 108 per night
Guest favourite

Guest suite in Chesapeake Beach

4.95 out of 5 average rating, 80 reviews

Nice Guest Suite at Chesapeake Bay

4–11 Dec

€ 144 per night
Guest favourite

Cottage in North Beach

4.95 out of 5 average rating, 75 reviews

Quiet Coastal Cottage Escape with Water Views

19–26 Mar

€ 181 per night
Guest favourite

Guest suite in North Beach

4.96 out of 5 average rating, 26 reviews

Brand New Guest Suite - Cozy 1 Bedroom Bungalow

18–25 Jun

€ 127 per night
Superhost

Flat in Huntingtown

4.87 out of 5 average rating, 15 reviews

Private Apartment On An Animal Sanctuary

26 Apr – 3 May

€ 96 per night
Guest favourite

Home in North Beach

4.9 out of 5 average rating, 21 reviews

Large Bungalow 2 Blocks to Beach

1–8 Aug

€ 190 per night
Superhost

Home in Huntingtown

5.0 out of 5 average rating, 7 reviews

Beach House on the Bay

11–18 Apr

€ 288 per night
Guest favourite

Home in North Beach

4.97 out of 5 average rating, 60 reviews

Charming Herrington / Rose Haven Cottage

6–13 Dec

€ 202 per night
Guest favourite

Home in North Beach

5.0 out of 5 average rating, 92 reviews

Waterfront Home w/ Hot Tub, Pets ok, Peleton

31 Oct – 7 Nov

€ 525 per night

Destinations to explore