Holiday Rentals in Chesapeake Beach

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Chesapeake Beach holiday rentals

Pool

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is €431
includes taxes & fees
20 May - 21 May
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (20 reviews)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is €264
includes taxes & fees
10 May - 11 May
Walk to Beach! King Bed & Free Beach Passes
Property grounds

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is €228
includes taxes & fees
10 May - 11 May
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (44 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is €316
includes taxes & fees
14 May - 15 May
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Marina

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is €429
includes taxes & fees
24 May - 25 May
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Smart TV

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is €455
includes taxes & fees
11 May - 12 May
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Beach

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is €396
includes taxes & fees
10 May - 11 May
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (3 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is €421
includes taxes & fees
26 May - 27 May
Sunset Cottage - West River Access and Views!
Smart TV, books

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is €386
includes taxes & fees
19 May - 20 May
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Sun-loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is €312
includes taxes & fees
10 May - 11 May
Cottage Located on the Patuxent River!
Beach

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Edgewater
9.0 out of 10, Wonderful, (7 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is €300
includes taxes & fees
10 May - 11 May
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Oven, stovetop

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
The price is €308
includes taxes & fees
23 May - 24 May
40' Bristol sailboat with spectacular views
Outdoor dining

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (44 reviews)
"The place was vey clean, whic is of upmost improtance to me. We loved the veiw and the location."
United States
Crystal H.
Sunset Breezes - quiet waterfront retreat
Outdoor dining

Waterfront Unit | Dock, Kayaks & SUPs Included

Waterfront Unit | Dock, Kayaks & SUPs Included
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
The price is €387
includes taxes & fees
11 May - 12 May
Waterfront Unit | Dock, Kayaks & SUPs Included
Games room

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
The price is €348
includes taxes & fees
10 May - 11 May
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Private kitchen

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
The price is €369
includes taxes & fees
10 May - 11 May
3-Bedroom Beach Home w/ Backyard
Beach nearby, sun-loungers, beach towels

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (14 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is €606
includes taxes & fees
1 Jun - 2 Jun
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is €500
includes taxes & fees
26 May - 27 May
Annapolis Retreat - 7 mins from downtown Annapolis!
Interior

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (20 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is €320
includes taxes & fees
9 Jun - 10 Jun
Bright and airy waterfront getaway
TV, offices

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is €584
includes taxes & fees
10 May - 11 May
Family Home on Mayo Peninsula | Deck | Sleeps 10
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake Beach Hotel Reviews

Holiday Inn Express Waldorf by IHG

Holiday Inn Express Waldorf by IHG

10/10 Excellent
"Clean room"
Dionna 2-night trip
Posted 5 hours ago
Holiday Inn Express Waldorf by IHG

Frequently asked questions

Can I find a holiday rental in Chesapeake Beach?

Yes, there are holiday rentals in Chesapeake Beach close to Chesapeake Beach Water Park, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Chesapeake Beach is known for its spas and beaches. While you're here, grab a bite or have a drink at the restaurants.

What are some of the best holiday rentals that Chesapeake Beach has to offer?

Private Cottage on gated estate: This holiday home rental outside of Chesapeake Beach is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Chesapeake Beach?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Chesapeake Beach stay.

What’s there to see and do in Chesapeake Beach?

Family-friendly attractions include Chesapeake Beach Water Park and Chesapeake Beach Railway Museum, whereas Breezy Point Beach and Northern Chesapeake Bay are a couple of great spots to enjoy the outdoors. Other places in town to visit include Rod n Reel Charter Fishing and Bruce Gabrielson's Surf Art Gallery and Museum.

What’s a holiday rental in Chesapeake Beach like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesapeake Beach. Holiday rentals provide amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for small groups.