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Deale Holiday Rentals

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Holiday Rentals in Deale

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

10.0 out of 10, Exceptional, (13)
"very serene, peaceful home on the bay! Amazing getaway! "
The price is AU$998
includes taxes & fees
4 Aug - 5 Aug
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (18)
"Loved the location, the property, and amenities. Would definitely stay again!"
The price is AU$1,198
includes taxes & fees
2 Aug - 3 Aug
Waterfront Sunset Bayview: sleeps 6

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

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is AU$535
includes taxes & fees
24 July - 25 July
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AU$428
includes taxes & fees
23 July - 24 July
Relax on Kent Island in 3 Bedroom Home w/Waterview

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is AU$2,165
includes taxes & fees
22 July - 23 July
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is AU$2,086
includes taxes & fees
22 July - 23 July
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

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

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. "
The price is AU$823
includes taxes & fees
4 Aug - 5 Aug
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (2)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is AU$788
includes taxes & fees
22 July - 23 July
Charming Pet-Friendly Stay - Near Bay & Beaches.

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

9.2 out of 10, Wonderful, (5)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is AU$765
includes taxes & fees
27 July - 28 July
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (51)
"This home is a wonderful place to stay. We enjoyed so much about it: the fully-equipped kitchen with spices and every appliance you might need, bathrooms with rain showers/good water pressure, decks for outdoor lounging, plenty of space and nice furnishings in the living room, and a quiet neighborhood that isn't too far away from the downtown area. We would love to come back again!"
The price is AU$1,291
includes taxes & fees
22 July - 23 July
Charming Annapolis WaterVIEW Home

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is AU$1,286
includes taxes & fees
22 July - 23 July
Charming Cottage with Hot Tub 1 Block from the Bay

Neptune by the Water

9.8 out of 10, Exceptional, (9)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is AU$834
includes taxes & fees
29 July - 30 July
Neptune by the Water

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
The price is AU$951
includes taxes & fees
29 July - 30 July
Annapolis Retreat - 7 mins from downtown Annapolis!

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (26)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
The price is AU$992
includes taxes & fees
5 Aug - 6 Aug
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

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

10.0 out of 10, Exceptional, (1)
"Stay there while my new home was getting work done, house was clean, perfect size for my family. It’s 50 ft to an ice cream shop and laundry mat. Our hoist even included a gift card to the ice cream shop. Great communication and perfect stay for us, felt like home "
The price is AU$738
includes taxes & fees
22 July - 23 July
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is AU$745
includes taxes & fees
4 Aug - 5 Aug
The Cottage

USNA Luxury Home, parking, pet friendly

10.0 out of 10, Exceptional, (8)
"Beautiful house in a great location to Main Street Annapolis. "
The price is AU$1,393
includes taxes & fees
23 July - 24 July
USNA Luxury Home, parking, pet friendly

Historic Row Home 1 Block from Gate 1 at USNA!

The price is AU$1,016
includes taxes & fees
22 July - 23 July
Historic Row Home 1 Block from Gate 1 at USNA!

Freshly renovated 3-story home 1 block from USNA!

9.8 out of 10, Exceptional, (34)
"We loved our stay! The property is lovely, well appointed and couldn’t be in a better location! We can’t wait to come back!"
The price is AU$1,004
includes taxes & fees
22 July - 23 July
Freshly renovated 3-story home 1 block from USNA!

Historic Row Home in Downtown Annapolis

The price is AU$972
includes taxes & fees
22 July - 23 July
Historic Row Home in Downtown Annapolis
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 Hotel Reviews

Frequently asked questions

Are there holiday rentals in Deale?

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

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Deale is located in the city centre, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Deale?

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

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 wider area, you’ll find Bayside History Museum and Rod n Reel Charter Fishing.

What’s a holiday rental in Deale like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Deale. Holiday rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family getaway.