Photo by Ronanne Vinson

Holiday Rentals in Chesapeake Beach

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Holiday Rentals in Chesapeake Beach

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

9.2 out of 10, Wonderful, (5)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is €385
includes taxes & fees
12 Jun - 13 Jun
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

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

10.0 out of 10, Exceptional, (209)
"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, (44)
"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, (57)
"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

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

9.8 out of 10, Exceptional, (181)
"A clean, comfortable getaway house, walking distance to St. Michaels and marinas, and well appointed."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Private Cottage on gated estate

10.0 out of 10, Exceptional, (23)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (35)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is €284
includes taxes & fees
12 Jun - 13 Jun
Relax on Kent Island in 3 Bedroom Home w/Waterview

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

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Wonderful property in a beautiful setting. We had a lovely weekend with family. Would highly recommend the property!"
Eastern Shore Waterside Cottage Near St. Michaels

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

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (175)
"Great time!! Floridians playing in the snow!! Cozy fire afterwards in the fireplace. Picturesque drive up to the Navy Cabin, deer playing in the snow too."
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

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

10.0 out of 10, Exceptional, (4)
"A few local spots to eat were great in the morning especially the Tighlman Market! Market has all you need to stock up with groceries and is just 2 minutes from the house."
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

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

9.8 out of 10, Exceptional, (38)
"Very clean, great location"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (28)
"Great location, close to the beach and restaurant. Cozy and comfortable, with a beautiful view of sunset. "
Chesapeake Houseboat Getaway on Kent Island, Maryland

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (247)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier

Waterfront Escape Near Annapolis

10.0 out of 10, Exceptional, (13)
"Good stay. Excellent location and facility es"
Waterfront Escape Near Annapolis

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

9.6 out of 10, Exceptional, (10)
"Property was in new condition, very well decorated and comfortable. A bit larger than what we needed; but, comfy."
The price is €349
includes taxes & fees
16 Jun - 17 Jun
Wright's Cottage- Pet's Welcome & EV Charging

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

10.0 out of 10, Exceptional, (1)
"We stayed here for 2 nights with 3 other couples. Bedrooms are very spacious. There are 2 rollaway beds and it looks like a pack n play as well for families with kids. Both couches pull out into beds. Everything was perfect for our needs. You can fit 3 cars in the front driveway but there’s also 2 spots available behind the house. You can also see the Bay from the front windows. Close to stores and gas as well. Would definitely recommend! "
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (119)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (26)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
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?

Relax on Kent Island in 3 Bedroom Home w/Waterview: This holiday home rental outside of Chesapeake Beach offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. 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.