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Chesapeake Beach Holiday Rentals

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Holiday Rentals in Chesapeake Beach

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

Chesapeake Beach
9.0 out of 10, Wonderful, (6)
"This house could not have a better location. There’s a gorgeous beach right across the street. My family and I spent many hours walking the beach looking for beach glass and shark teeth, which were surprisingly plentiful. There was even a nice dock to fish on. The house is very well kept. The upstairs table on the patio was a favorite of mine. The owner was in constant contact. We had a blast."
United States
Jeff B.
The price is NZ$762
includes taxes & fees
14 Dec - 15 Dec
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Edgewater
The price is NZ$5,543
includes taxes & fees
14 Nov - 15 Nov
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Waterfront Getaway, Dock Your Boat & Play!

Edgewater
10.0 out of 10, Exceptional, (3)
"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 NZ$553
includes taxes & fees
17 Nov - 18 Nov
Waterfront Getaway, Dock Your Boat & Play!

Sunset Cottage - West River Access and Views!

2.0 star property
Shady Side
The price is NZ$833
includes taxes & fees
18 Nov - 19 Nov
Sunset Cottage - West River Access and Views!

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

Owings
10.0 out of 10, Exceptional, (48)
"Lovely property."
United States
Melissa W.
The price is NZ$419
includes taxes & fees
16 Nov - 17 Nov
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
The price is NZ$454
includes taxes & fees
16 Nov - 17 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

2.0 star property
North Beach
10.0 out of 10, Exceptional, (1)
"Great location! Everything was on hand and it was an easy sweet little cottage to be in.It was clean and very functional with the added bonus of being so close to all the activity in North Beach.Heather was responsive and obviously cares about her guests and their stay.Highly recommend! "
United States
Georgina P.
The price is NZ$489
includes taxes & fees
15 Nov - 16 Nov
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Walk to Beach! King Bed & Free Beach Passes

North Beach
10.0 out of 10, Exceptional, (16)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is NZ$624
includes taxes & fees
1 Dec - 2 Dec
Walk to Beach! King Bed & Free Beach Passes

Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

Port Republic
9.4 out of 10, Exceptional, (6)
"Great place to stay. Quiet comfortable neighborhood, plenty to do around if you’re outdoorsy. The location was comfortable & well stocked with anything you’d need. Would return. "
United States
Caleb R.
The price is NZ$312
includes taxes & fees
14 Nov - 15 Nov
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is NZ$853
includes taxes & fees
9 Dec - 10 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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

Benedict
9.0 out of 10, Wonderful, (6)
"Sophia the host is super attentive and responsive"
United States
Mayela
The price is NZ$529
includes taxes & fees
14 Nov - 15 Nov
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Beautiful Waterfront Retreat in Cambridge!

Cambridge
10.0 out of 10, Exceptional, (49)
"Wonderful stay. The Crab Shack and dock were the highlights. We spent most of our time there. It was awesome. Highly recommend. "
United States
Christopher D.
The price is NZ$706
includes taxes & fees
16 Nov - 17 Nov
Beautiful Waterfront Retreat in Cambridge!

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Shady Side
10.0 out of 10, Exceptional, (4)
"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "
United States
Mark E.
The price is NZ$757
includes taxes & fees
14 Nov - 15 Nov
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Cottage Located on the Patuxent River!

Prince Frederick
10.0 out of 10, Exceptional, (42)
"Nice and quiet beautiful cottage. A+ communication and a gem. 10/10 will stay again."
United States
chris W.
The price is NZ$561
includes taxes & fees
14 Nov - 15 Nov
Cottage Located on the Patuxent River!

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

Prince Frederick
9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is NZ$693
includes taxes & fees
16 Nov - 17 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

#2 Egret Cottage Harris Cove

Saint Michaels
10.0 out of 10, Exceptional, (1)
The price is NZ$678
includes taxes & fees
26 Nov - 27 Nov
#2 Egret Cottage Harris Cove

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

Arundel on the Bay
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is NZ$865
includes taxes & fees
19 Nov - 20 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater
9.8 out of 10, Exceptional, (24)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
United States
Mireia A.
The price is NZ$1,013
includes taxes & fees
18 Nov - 19 Nov
Edgewater/Mayo Gateaway w/ Hot Tub

Lakefront Log Cabin Retreat 3br-2ba Hot Tub+kayaks

3.0 star property
Lusby
The price is NZ$1,283
includes taxes & fees
14 Nov - 15 Nov
Lakefront Log Cabin Retreat 3br-2ba Hot Tub+kayaks

Holly Hill Haven - Sleeps 10

Edgewater
10.0 out of 10, Exceptional, (3)
"Only thing is I would better stock the kitchen. Other than that NO COMPLAINTS! Great location, great clean and comfortable home to host thanksgiving "
United States
Brittany B.
The price is NZ$897
includes taxes & fees
9 Dec - 10 Dec
Holly Hill Haven - 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

Find out more about Chesapeake Beach

Everything you need to know about Chesapeake Beach holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake Beach holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake Beach holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesapeake Beach holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake Beach. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake Beach holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake Beach holiday rentals we have selected for you start as low as NZ$454 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesapeake Beach rentals

At Expedia, we put the best Chesapeake Beach holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesapeake Beach rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake Beach holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub: This holiday home rental outside of Chesapeake Beach is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

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 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.