Deale Beach Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Deale Beach

Fridge, microwave, oven, stovetop
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic District
10.0 out of 10, Exceptional, (32)
"The location is fabulous. We could walk wherever we wanted to go. The room to bathroom ration was also great. We would stay here again. "
United States
Diana L.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Marina
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
Stevensville
6.4 out of 10, (7)
"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
Fridge, microwave, oven, stovetop
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville
10.0 out of 10, Exceptional, (15)
"Very clean beautiful house! We stayed there for a wedding weekend and it was perfect. Great location. The hosts were wonderful and got back to us right away! Would love to go back one day."
United States
Tammy S.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

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

Port Republic
10.0 out of 10, Exceptional, (180)
"Wonderful cabin right on the Chesapeake Bay. Quiet and private. Lots of parks and good restaurants in the general area. We thoroughly enjoyed our stay."
United States
Suzanne M.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Fridge, microwave, oven, stovetop
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Historic District
9.4 out of 10, Exceptional, (18)
"The gigantic house was perfect for our quick Army-Navy Football game weekend. We hope to come back when it’s warm to take advantage of the great gathering spaces outdoors. Go Navy! Beat Army!!"
United States
Elizabeth B.
The price is AU$1,796
includes taxes & fees
25 Nov - 26 Nov
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

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

Tracys Landing
9.8 out of 10, Exceptional, (50)
"The house was so beautiful from top to bottom! It was incredibly well stocked on everything that we needed and we had an incredible weekend! The hosts were very responsive when needed and we can't speak higher about how wonderful this property is! We will certainly be back! "
United States
Julie S.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!

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 AU$478
includes taxes & fees
16 Nov - 17 Nov
Waterfront Getaway, Dock Your Boat & Play!
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

St. Michaels
9.8 out of 10, Exceptional, (44)
"This cottage is adorable. Great amenities and great location. We thoroughly enjoyed our time in St Michael’s."
United States
Audra B.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Property grounds
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Crofton
9.6 out of 10, Exceptional, (97)
"Food options where very good, there was more than enough options to choose from (which we loved). "
United States
Marcus
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels
9.6 out of 10, Exceptional, (146)
"Perfect place to stay for a cousins reunion, Central location to all the shops and restaurants."
United States
Amh S.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Interior
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

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

Stevensville
10.0 out of 10, Exceptional, (55)
"My wife and I have stayed at many different places over the years but this may be one of the most well maintained properties I've ever seen. It was a great place for us to unwind with our dog and we would certainly recommend this location for anyone looking to stay in the area"
United States
Nick B.
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub

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 AU$875
includes taxes & fees
19 Nov - 20 Nov
Edgewater/Mayo Gateaway w/ Hot Tub
Outdoor dining
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Luxury Waterfront Executive Family Home Annapolis with All Amenities

Annapolis
7.0 out of 10, Good, (6)
"We enjoyed unforgettable moments, thank you"
United States
Jonatan B.
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Cape Saint Claire
10.0 out of 10, Exceptional, (38)
"Fabulous week! Our family of 3 generations had a blast and appreciated the outstanding accommodations. House and outdoor areas are beautiful and well-maintained. Excellent location close to amenities and just minutes from Annapolis. Everything was great!"
United States
Melissa K.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Dining
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Cape St. John
10.0 out of 10, Exceptional, (111)
"We had a wonderful time."
United States
bruce b.
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Exterior
Modern Flat in the Heart of St. Michaels – Walk Everywhere

Modern Flat in the Heart of St. Michaels – Walk Everywhere

Saint Michaels
10.0 out of 10, Exceptional, (53)
"Beautiful, clean and well appointed in the perfect spot in downtown Saint Michael’s. Highly recommended!!"
United States
Jeffrey G.
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Fridge, microwave, oven, stovetop
Sweet Bamboo Beach Cottage

Sweet Bamboo Beach Cottage

north beach
10.0 out of 10, Exceptional, (82)
"This property is lovely. So close to my daughter it’s a perfect weekend getaway. "
United States
Sheila P.
Sweet Bamboo Beach Cottage
Private beach
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Sherwood
10.0 out of 10, Exceptional, (19)
"Gorgeous views and location. "
United States
Ryan D.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Marina
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Historic District
10.0 out of 10, Exceptional, (239)
"A great experience all around"
United States
Daniel m.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Exterior detail
Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown

Historic District
9.6 out of 10, Exceptional, (15)
"We had a very lovely stay . This is an excellent location . "
United States
Kimberly B.
The price is AU$1,237
includes taxes & fees
16 Nov - 17 Nov
Secluded Cozy Cottage in Historic Downtown
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 Deale Beach Hotel Reviews

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

10/10 Excellent
"Good location and staff "
Michael 3-night trip
Posted 23 hours ago
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

Find out more about Deale Beach

Everything you need to know about Deale 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 Deale 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 Deale Beach holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Deale Beach holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Deale 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 Deale 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 Deale Beach holiday rentals we have selected for you start as low as AU$478 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Deale Beach rentals

At Expedia, we put the best Deale 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 Deale 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 Deale 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 Deale 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

Are there holiday rentals in Deale Beach?

Yes, there are holiday rentals close to the most popular sights in Deale Beach, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Deale Beach has to offer?

Million Dollar View of the Chesapeake Bay: This highly rated holiday home rental in Deale Beach is located on the waterfront, and has a balcony, a private garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Deale Beach?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Deale Beach stay.

What’s there to see and do in Deale Beach?

Northern Chesapeake Bay and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Shadyside Park and Chesapeake Beach Water Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Deale Beach like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Deale Beach. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the experience 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 an attractive option for a family getaway.