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Deale Holiday Rentals

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Holiday Rentals in Deale

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
10.0 out of 10, Exceptional, (73)
"The cottage provides a wonderful way to experience Deale and the surrounding area. Well equipped and clean, I had everything I needed and didn't want to leave,"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Million Dollar View of the Chesapeake Bay
Beach/ocean view
Million Dollar View of the Chesapeake Bay
9.8 out of 10, Exceptional, (107)
"Such a beautiful spot! The house has everything and the owners perfect."
Million Dollar View of the Chesapeake Bay
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, (2)
"My rugby team traveled down for a competition. Erin met us there walked us around the property and gave us great recommendations for food in the area. She was an amazing manager, always answering questions and getting us anything we needed. The property was beautiful and fit our entire team comfortably. The large slace and outdoor activity allowed for a lot of team building and we had a blast llaying pickle ball and basketball with each other. We wish we coukd have spent more time there."
The price is AU$2,139
includes taxes & fees
7 May - 8 May
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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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, (186)
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
The Blue Crab Beach House - Free beach passes
Beach nearby, sun-loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (37)
"This property is in a great location! The house is adorable and the owner was very responsive and accommodating when I needed to add an extra day. I would definitely recommend!"
The Blue Crab Beach House - Free beach passes
Directly Across from Gate One & Steps from the Waterfront
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (178)
"Great location! The owner was very easy to communicate with and very accommodating. We had a great time exploring Annapolis."
Directly Across from Gate One & Steps from the Waterfront
Charming Annapolis WaterVIEW Home
Property grounds
Charming Annapolis WaterVIEW Home
9.8 out of 10, Exceptional, (41)
"We were friends gathering for a visit to relax and catch up and the house was perfect for that! It was very comfortable, in a quiet neighborhood, but close to enjoy going to local restaurants and shopping. We loved the large windows that looked out over the Bay! The decor was unique interesting touches."
The price is AU$1,034
includes taxes & fees
8 May - 9 May
Charming Annapolis WaterVIEW Home
Pool and Bay Views on wrap around deck in Kent Island
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (25)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Property grounds
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (22)
"My family and I had an amazing stay!! Jacob’s correspondence was timely and very friendly from beginning to end. We had some problems with cleanliness (sheets not being washed, cobwebs, dead beetles in windowsills), and Jacob refunded our cleaning fee. Despite that, the house was beautiful and had plenty of space for our big family to move around. Be warned that there are A LOT of stairs! But nothing my older parents couldn’t handle. The views are absolutely breathtaking and every single room...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Relax on Kent Island in 3 Bedroom Home w/Waterview
Exterior
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (19)
"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"
The price is AU$595
includes taxes & fees
2 June - 3 June
Relax on Kent Island in 3 Bedroom Home w/Waterview
Amazing views, short walks to great dining!
Smart TV, Netflix, DVD player, streaming services
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (63)
"My husband and I stayed at the Weems creek cottage for a childless getaway weekend. Everything was excellent, from communication with Jim, to the gorgeous property and the time we had in the city of Annapolis. Not to mention the weather was nice! We spent Friday and most of Saturday in the city of Annapolis. On Saturday evening we just enjoyed our stay at the cottage, we had two fires, relaxing in the Adirondack chairs overlooking the water. THIS was exactly what we needed and what we enjoy...
Amazing views, short walks to great dining!
Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (43)
"Laura’s house is so nice and comfortable. It has everything you could need and more. The backyard is such a great space. My one and only complaint/warning is that the front bedrooms were noisy at night because of the cars/traffic going by. This is nothing a white noise machine can’t fix. We would still definitely stay there again!("
Recently Renovated Annapolis Home - Conveniently Located
Waterfront Cottage on the Eastern Shore
Fridge, microwave, oven, stovetop
Waterfront Cottage on the Eastern Shore
The price is AU$1,542
includes taxes & fees
9 May - 10 May
Waterfront Cottage on the Eastern Shore
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
TV
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
9.6 out of 10, Exceptional, (7)
"I have to tell the whole story sorry it is a little long but amazing. We had booked with VRBO at another location to come up for my mother in laws funeral services. We had to change the date last minute so VRBO helpfully accommodated us and gave us another offered us another location we agreed and found out it was the house next to the house my husband grew up in and his Mother had just told us how much she loved that house. They lived they over 50 years ago. We had the best time invited family...
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Charming Cottage with Hot Tub 1 Block from the Bay
Property grounds
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (6)
"Was a super comfortable spot my 5 friends and I. Super comfy couches and beds, nice TV, well appointed kitchen. Took a nice walk down to the water in the am. Would stay again!"
The price is AU$826
includes taxes & fees
7 May - 8 May
Charming Cottage with Hot Tub 1 Block from the Bay
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (78)
"Liz, the host, was one of the nicest and most accommodating hosts I have ever had the pleasure to work with. She allowed me and a few of my bridesmaids to get ready in her home for my wedding a few blocks away. It was the perfect location. Fully equipped with whatever we needed, meticulously well-decorated and maintained, and surprisingly spacious for our needs. The beds were very comfortable for some much needed rest. Liz’s garden is incredible. I definitely recommend a spring visit for that...
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
Exterior
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
10.0 out of 10, Exceptional, (57)
"My wife and I stayed here for a weekend and everthing was perfect. The house looks professionally decorated and sits in a very quiet and safe neighbohhod that was fun to walk for miles. As night falls, the enchanting lights in the backyard transform the space into a serene oasis, inviting you to unwind under the stars. The addition of a hot tub and corn hole adds a playful touch, perfect for relaxation and entertainment. Our stay was nothing short of perfection. Pat and Ken were great host and...
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Fridge, microwave, oven, stovetop
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (98)
"This property is ideal for a family. Very nicely decorated and ample room. The off street parking in Eastport is rare and makes this property well worth a stay."
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Cozy place close to the city dock
Beach
Cozy place close to the city dock
10.0 out of 10, Exceptional, (52)
"We were in town for a family wedding, and we also able to enjoy the atmosphere of downtown Annapolis."
Cozy place close to the city dock
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See all available properties in Deale
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.

Other types of properties in Deale you may be interested in

Anchored Inn at Hidden Harbour Marina
Front of property
Anchored Inn at Hidden Harbour Marina
2.5 star property
9.4 out of 10, Exceptional, (363)
"Would stay here again "
The price is AU$429
includes taxes & fees
7 May - 8 May
Anchored Inn at Hidden Harbour Marina
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Exterior
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
2.5 star property
6.6 out of 10, (1207)
"Pleasant stay "
The price is AU$155
includes taxes & fees
12 May - 13 May
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Historic Inns of Annapolis
Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1612)
"Weekend was great despite the weather. Always love staying at the Maryland Inn. Great location and quiet!"
The price is AU$297
includes taxes & fees
13 May - 14 May
Historic Inns of 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.

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

Deale holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Deale. 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 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 holiday rentals we have selected for you start as low as AU$595 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Deale rentals

At Expedia, we put the best Deale 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 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 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. 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?

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?

Rockhold Creek Cottage, Water Front, Vacation Home, Docks: This highly rated holiday home rental in Deale is located on a river, and has a balcony, a garden 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 7 Expedia holiday rentals in Deale for a memorable holiday.

What’s there to see and do in Deale?

Enjoy the area's cultural attractions such as Galesville Heritage Museum, or get outdoors into nature at a spot like Breezy Point Beach. In the wider area, you’ll find Chesapeake Beach Water Park 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.

Recent reviews of Deale properties
Expedia verified reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

5/5 Excellent
May 4th
"Weekend was great despite the weather. Always love staying at the Maryland Inn. Great location and quiet!"
A verified traveller stayed at Historic Inns of Annapolis
Posted 1 day ago
Historic Inns of Annapolis