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Deale Vacation Rentals

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Check prices for these dates

Tonight
Apr 18 - Apr 19
Tomorrow
Apr 19 - Apr 20
This weekend
Apr 18 - Apr 20
Next weekend
Apr 25 - Apr 27

Vacation Rentals in Deale

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Property grounds

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Ritchie, our host was extremely accommodating. Home looked exactly like the pictures. Very clean and comfortable. Water front! Many good restaurants within walking distance."
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Million Dollar View of the Chesapeake Bay
Dining

Million Dollar View of the Chesapeake Bay

9.8 out of 10, Exceptional, (120)
"We had the pleasure of staying at this incredible vacation rental, and we can’t recommend it enough! From the moment we arrived, we were charmed by the house's beauty and functionality.The kitchen is fully stocked with everything you could possibly need – whether you're cooking a full meal or just making a quick snack, you'll find all the tools, gadgets, and appliances to make it happen.The bathrooms are well-equipped with towels, toiletries, toilet paper.Plenty of space to relax and unwind...
Million Dollar View of the Chesapeake Bay
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (212)
"The house was absolutely perfect for our USNA Reunion. About 10 steps to Gate 1 and just a few more to the heart of downtown made it a weekend we will remember. The host was responsive and accommodated our requests and was very kind. I would definitely stay here again."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Property grounds

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

9.6 out of 10, Exceptional, (74)
"Nothing like home away from home!! Very comfortable home. Thank you. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Chesapeake Houseboat Getaway on Kent Island, Maryland
Smart TV, fireplace

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (25)
"Rainy weather limited activities but would return to property"
Chesapeake Houseboat Getaway on Kent Island, Maryland
The Blue Crab Beach House - Free beach passes
Fridge, microwave, oven, stovetop

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"Cute as a button. Very, very clean, kitchen has everything, living room very comfortable for us 4 adults. Fenced yard was perfect for our furry companion. Excellent location-quiet neighborhood, easy walk to beach and restaurants.Host is very prompt responding to any inquiry. You won’t regret this rental!!"
The Blue Crab Beach House - Free beach passes
Charming Home Away From Home
Living area

Charming Home Away From Home

2.0 star property
10.0 out of 10, Exceptional, (3)
"We stayed at this property in transition from out of the country back to the states due to military orders. We stayed here for 2 months and were very comfortable. Coco was a great host with a beautiful property and allowed us to have our dog and two cats here. It is a basement apartment that is very spacious and is about the size of a standard one bedroom apartment. I would recommend staying here to anyone, short or long stays! Coco was very responsive and was great with communication. It is...
Charming Home Away From Home
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
Fridge, microwave, oven, stovetop

Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

10.0 out of 10, Exceptional, (7)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is CA $994
CA $1,633 total
includes taxes & fees
Apr 21 - Apr 22
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Exterior

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

10.0 out of 10, Exceptional, (39)
"This place is great. From the layout, to the sauna, screened in porch and backyard, the owners have thought hard about what features make for a luxurious, comfortable and fun experience. They were also very helpful with all aspects of the process - booking, arrival times, access to the home, help with what to do while there. "
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is CA $270
CA $527 total
includes taxes & fees
Apr 20 - Apr 21
The Cottage
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, (34)
"Clean, Spacious, and exactly as advertised! "
The price is CA $105
CA $349 total
includes taxes & fees
Apr 20 - Apr 21
Relax on Kent Island in 3 Bedroom Home w/Waterview
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Smart TV

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (27)
"Nice and peaceful stay for a quick local getaway. "
The price is CA $112
CA $362 total
includes taxes & fees
Apr 23 - Apr 24
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Romantic Two Bedroom Condo
Fridge, microwave, oven, stovetop

Romantic Two Bedroom Condo

10.0 out of 10, Exceptional, (71)
"Nice little two bedroom with everything you need. Food is conveniently close. If simple is what you are looking for this fits."
Romantic Two Bedroom Condo
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (25)
"Really enjoyed my stay at Erin’s place. The space is incredible, really clean and modern. Walls are thick and beds were incredibly comfortable. We really enjoyed all the amenities as well: kayaking in the lake, pickleball and basketball.A few notes: because it is by the lake, there were a lot of bugs when we went. As part of the check-in process, Erin does need to walk you through the house. She lives an hour away so there needs to be some level of coordination there. As a result, the neighbors...
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
The Lazy Crab Beach House - Free beach passes
Exterior

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (46)
"Exactly as described. Appreciated coffee & cream upon arrival too."
The Lazy Crab Beach House - Free beach passes
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Terrace/patio

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

10.0 out of 10, Exceptional, (174)
"The Navy cabin was just as pictured/described and Brett was a pleasure to deal with. The views were spectacular and we greatly enjoyed exploring the small beaches nearby. A day trip to Solomon‘s capped off our stay. Would love to go back and enjoy the serene nature of this rental."
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
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, (207)
"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
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, (43)
"Quiet and tranquil. Nicely decorated and will definitely stay here again when we return to the area. "
The price is CA $221
CA $430 total
includes taxes & fees
Apr 20 - Apr 21
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (73)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is CA $346
CA $650 total
includes taxes & fees
Apr 20 - Apr 21
Waterfront Oasis of Annapolis Star
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Interior

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (113)
"This place was a wonderful spot for our family to have a long weekend getaway. It's on a bluff right next to the ocean with a glorious view and a stairway access to the beach. The beds are comfortable, the house has lots of great spaces to relax or play games, and the beach is a wonderful space to explore, find seashells and possibly a fossil sharks tooth (we had no luck there, but we did find a whale vertebrae, so that's something!). But in any event, we highly recommend! "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
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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Other types of properties in Deale you may be interested in

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Property grounds

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Ritchie, our host was extremely accommodating. Home looked exactly like the pictures. Very clean and comfortable. Water front! Many good restaurants within walking distance."
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1738)
"Attentive! Clean, well decorated. Perfect location"
The price is CA $234
CA $314 total
includes taxes & fees
Apr 20 - Apr 21
Historic Inns of Annapolis
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Exterior

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

3.0 star property
6.2 out of 10, (1567)
"Staff was very friendly. The only downfall was the elevator. One was broken and the other was kinda sketchy and suuuuper slow. "
The price is CA $121
CA $138 total
includes taxes & fees
Apr 20 - Apr 21
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
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.

Frequently asked questions

Are there vacation rentals in Deale?

Yes, we give you a choice of vacation rentals near the most popular sights in Deale, or you can go with a more remote option if you want a relaxing place to stay. Deale is known for its waterfront and bars. Make sure you have time to check out the shopping and live music during your trip.

What are some of the best vacation rentals in Deale?

Rockhold Creek Cottage, Water Front, Vacation Home, Docks: Visitors like this Deale vacation home rental. It is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease 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. You and your friends and family can relax into your vacation with amenities like a selection of games. Another good choice for your trip to Deale is Million Dollar View of the Chesapeake Bay.

How many vacation rentals are there in Deale?

Choose from 8 Expedia vacation rentals in Deale for a memorable vacation.

What’s there to see and do in Deale?

While exploring the area, visit family-friendly sights like Chesapeake Beach Water Park, or get outside and enjoy nature at Shadyside Park. In the larger area, you’ll find Rod n Reel Charter Fishing and Chesapeake Beach Railway Museum.

What’s a vacation rental in Deale like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Deale. Vacation rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.