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Chesapeake Beach Vacation Rentals

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Check prices for these dates

Tonight
Jun 19 - Jun 20
Tomorrow
Jun 20 - Jun 21
This weekend
Jun 20 - Jun 22
Next weekend
Jun 27 - Jun 29

Vacation Rentals in Chesapeake Beach

Family Beach House: Spacious Deck, Grill & Views
Pool

Family Beach House: Spacious Deck, Grill & Views

9.2 out of 10, Wonderful, (5)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is ￥26,100
￥64,888 total
includes taxes & fees
Jul 1 - Jul 2
Family Beach House: Spacious Deck, Grill & Views
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior

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

10.0 out of 10, Exceptional, (210)
"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
Interior

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
Exterior detail

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (58)
"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
Outdoor dining

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
Family and Pet-Friendly, Waterfront with Pier
Exterior

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
Private Cottage on gated estate
Property grounds

Private Cottage on gated estate

10.0 out of 10, Exceptional, (24)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate
Dollhouse in Central Historic St Michaels
Exterior

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
Smart TV

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (36)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is ￥24,208
￥55,325 total
includes taxes & fees
Jun 30 - Jul 1
Relax on Kent Island in 3 Bedroom Home w/Waterview
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is ￥31,900
￥68,930 total
includes taxes & fees
Jul 7 - Jul 8
The Cottage
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Dining

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

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
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (40)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (39)
"Very clean, great location"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Wright's Cottage- Pet's Welcome & EV Charging
TV, offices

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

9.8 out of 10, Exceptional, (11)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
The price is ￥20,300
￥58,186 total
includes taxes & fees
Jun 20 - Jun 21
Wright's Cottage- Pet's Welcome & EV Charging
Chesapeake Houseboat Getaway on Kent Island, Maryland
Smart TV, fireplace

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

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
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Outdoor pool

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

10.0 out of 10, Exceptional, (44)
"We had a great stay! Thanks."
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Waterfront Escape Near Annapolis
TV, table tennis

Waterfront Escape Near Annapolis

10.0 out of 10, Exceptional, (13)
"Good stay. Excellent location and facility es"
Waterfront Escape Near Annapolis
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.
3 bedrooms, iron/ironing board, WiFi, bed sheets

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.
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 vacation rental in Chesapeake Beach?

Yes, you can find vacation rentals in Chesapeake Beach near Chesapeake Beach Water Park, or you can select a more remote option if you're looking for extra privacy while you relax. 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 vacation home rentals that Chesapeake Beach has to offer?

Relax on Kent Island in 3 Bedroom Home w/Waterview: This vacation home near 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 you can cook with friends or family.

How many vacation rentals will I find in Chesapeake Beach?

With 9 Expedia vacation rentals, you're sure 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 vacation rental in Chesapeake Beach like?

Vacation rentals are privately owned properties you can book for several days or longer in Chesapeake Beach. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.