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Chesapeake Beach Holiday Rentals

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Holiday Rentals in Chesapeake Beach

The Cozy Crab- Your Charming Haven in Lovely North Beach!
9.8 out of 10, Exceptional, (12)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
United States
scott
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
7.0 out of 10, Good, (6)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (50)
"Our large family of adults and two one-year-olds and a dog had a perfect week. The hosts were kind and responsive, and the home was spacious with lots of room for privacy and being all together. Looking forward to going again!"
United States
Lynne J.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (121)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
10.0 out of 10, Exceptional, (180)
"First, Brett is an exceptional host. Very helpful and responsive. This is a very special place in a wonderful community with incredible views. Rustic, warm and the perfect place to relax. We didn’t want to leave! Highly recommend."
United States
Dee D.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Waterfront Getaway, Dock Your Boat & Play!
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 AU$483
includes taxes & fees
26 Oct - 27 Oct
Waterfront Getaway, Dock Your Boat & Play!
Million Dollar View of the Chesapeake Bay
9.8 out of 10, Exceptional, (129)
"We just enjoyed our fourth year at Million Dollar View of the Chesapeake Bay and already look forward to our next vacation at this wonderful home!"
United States
Melissa G.
Million Dollar View of the Chesapeake Bay
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
United States
Ronald S.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (13)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
United States
Dara M.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is AU$477
includes taxes & fees
16 Nov - 17 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview
Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (262)
"This was an extension of our original 4-day stay. We had so much wonderful and fun time that we stayed an extra day. The owners Rob and Clarissa were the best host!"
United States
Alicia J.
Family and Pet-Friendly, Waterfront with Pier
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
10.0 out of 10, Exceptional, (18)
"House was great and the golf cart excellent"
United States
Bradley E.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Edgewater/Mayo Gateaway w/ Hot Tub
9.8 out of 10, Exceptional, (23)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
The price is AU$946
includes taxes & fees
30 Oct - 31 Oct
Edgewater/Mayo Gateaway w/ Hot Tub
Dollhouse in Central Historic St Michaels
9.6 out of 10, Exceptional, (55)
"Great location. House is old and therefore a little quirky, but overall comfortable. "
United States
Karen L.
Dollhouse in Central Historic St Michaels
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
9.8 out of 10, Exceptional, (43)
"House was beautiful! Right on the bay and easily accommodated our group. "
United States
James T.
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.6 out of 10, Exceptional, (5)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
United States
Berenice N.
The price is AU$464
includes taxes & fees
28 Oct - 29 Oct
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (220)
"Very nice place, we will be visiting again!"
United States
Karen B.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (124)
"We had a wonderful stay. This was our second time staying here and we loved it. Very quay, cozy and clean. Everything as advertised. Location is perfect as it is a very walkable town. This place is right in the middle. The owner was very friendly, open and communicative. And I had a big surprise when we returned. My neck pillow I had forgotten and left it 2 years ago was still there sitting in a closet. We hope to return next year. "
United States
David W.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (75)
"Wonderful property within walking distance to the beach and a number of restaurants. Great communication and easy process. "
United States
Heather H.
The Blue Crab Beach House - Free beach passes
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (144)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
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 favourite 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 depend 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 AU$464 per night. Entering your travel dates in the search wizard might find you 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.