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

Guest suite in Lusby

4.99 out of 5 average rating, 299 reviews

Riverfront 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

$175 SGD per night
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.

4–11 Nov

$176 SGD 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.

11–18 Dec

$369 SGD 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

Cottage in California

4.97 out of 5 average rating, 190 reviews

Cozy Little Cottage

13–20 Nov

$120 SGD per night
Guest favourite

Home in Shady Side

5.0 out of 5 average rating, 113 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

18–25 Mar

$648 SGD per night
Guest favourite

Cottage in Colonial Beach

4.93 out of 5 average rating, 176 reviews

Cozy cottage 3 blocks from beach

13–20 Jan

$165 SGD per night
Guest favourite

Home in North Beach

4.86 out of 5 average rating, 58 reviews

Light of North Beach

15–22 Jul

$134 SGD 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

$188 SGD 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

$206 SGD 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

17–24 Jun

$163 SGD per night
Superhost

Serviced apartment in Huntingtown

4.87 out of 5 average rating, 15 reviews

Private Apartment On An Animal Sanctuary

26 Apr – 3 May

$137 SGD per night
Guest favourite

Home in North Beach

4.9 out of 5 average rating, 21 reviews

Large Bungalow 2 Blocks to Beach

14–21 Apr

$241 SGD per night
Guest favourite

Home in North Beach

4.97 out of 5 average rating, 60 reviews

Charming Herrington / Rose Haven Cottage

23–30 Sep

$246 SGD per night
Guest favourite

Bungalow in North Beach

4.88 out of 5 average rating, 64 reviews

Bayside Bungalow: Cozy North Beach Getaway

12–19 Nov

$258 SGD per night
Guest favourite

Home in North Beach

4.98 out of 5 average rating, 46 reviews

Cheerful Two Bedroom Home on the Chesapeake Bay!

17–24 Oct

$347 SGD per night

Destinations to explore