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Chesapeake Beach Holiday Rentals

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Holiday Rentals in Chesapeake Beach

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (211)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (45)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (61)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes

Private Cottage on gated estate

10.0 out of 10, Exceptional, (24)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (248)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (182)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (31)
"Great location, close to the beach and restaurant. Cozy and comfortable, with a beautiful view of sunset. "
Chesapeake Houseboat Getaway on Kent Island, Maryland

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (159)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek

The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (49)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (37)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is NZ$499
includes taxes & fees
30 June - 1 July
Relax on Kent Island in 3 Bedroom Home w/Waterview

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

10.0 out of 10, Exceptional, (102)
"Had a wonderful, peaceful stay."
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is NZ$742
includes taxes & fees
7 July - 8 July
The Cottage

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (6)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Edgewater/Mayo Getaway!

9.8 out of 10, Exceptional, (17)
"We had a wonderful experience with our latest stay. They were flexible on arrival time, beds were very comfortable and the house was very comfortable! Will definitely stay again!"
The price is NZ$896
includes taxes & fees
9 July - 10 July
Edgewater/Mayo Getaway!

Bright and airy waterfront getaway

9.8 out of 10, Exceptional, (13)
"This property was everything we wanted. We hope to return next year."
Bright and airy waterfront getaway

Wright's Cottage- Pet's Welcome & EV Charging

9.0 out of 10, Wonderful, (12)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
The price is NZ$668
includes taxes & fees
30 June - 1 July
Wright's Cottage- Pet's Welcome & EV Charging

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"Great stay"
The Lazy Crab Beach House - Free beach passes

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (40)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

10.0 out of 10, Exceptional, (33)
"Great stay"
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
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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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 9 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 is a spot 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.