An aerial view of a beach with clear water, a sandy shore, and visible footprints.

Deale Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Deale holiday rentals

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

1. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Lovely ! "
United States
Ellen B.
The price is HK$669
HK$2,608 total
includes taxes & fees
26 Aug - 27 Aug
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A house with a yellow door and a window with a lamp outside.

2. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is HK$1,023
HK$2,614 total
includes taxes & fees
3 Sept - 4 Sept
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

3. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (37 reviews)
"Such a great house! "
United States
Stephanie V.
The price is HK$1,228
HK$3,804 total
includes taxes & fees
8 Sept - 9 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A deck with outdoor furniture, a red door, and a house with siding.

4. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
The price is HK$1,256
HK$2,862 total
includes taxes & fees
30 Aug - 31 Aug
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

5. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (54 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is HK$1,133
HK$2,753 total
includes taxes & fees
31 Aug - 1 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

6. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is HK$2,124
HK$4,558 total
includes taxes & fees
8 Sept - 9 Sept
3-bedroom house in Deale located on Bay many amenities and great views
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

7. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
The price is HK$2,140
HK$4,220 total
includes taxes & fees
9 Sept - 10 Sept
Sunset Cottage - West River Access and Views!
A lighthouse with a white exterior, a balcony, and a metal roof.

8. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is HK$1,133
HK$2,687 total
includes taxes & fees
31 Aug - 1 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

9. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$2,070
HK$5,774 total
includes taxes & fees
27 Aug - 28 Aug
Family Home on Mayo Peninsula | Deck | Sleeps 10
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

10. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,561
HK$4,462 total
includes taxes & fees
15 Sept - 16 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

11. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is HK$2,137
HK$3,639 total
includes taxes & fees
22 Aug - 23 Aug
Plum Point Cottage #17

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is HK$1,522
HK$4,087 total
includes taxes & fees
21 Sept - 22 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

13. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is HK$1,501
HK$3,973 total
includes taxes & fees
26 Aug - 27 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

14. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (12 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is HK$1,780
HK$4,728 total
includes taxes & fees
1 Sept - 2 Sept
Renovated Bungalow | Walk to Beach | Dog-Friendly
A beach with chairs and a pier in the background.

15. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$2,541
HK$5,096 total
includes taxes & fees
25 Aug - 26 Aug
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

16. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is HK$1,932
HK$5,071 total
includes taxes & fees
23 Aug - 24 Aug
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

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

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (15 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is HK$2,593
HK$4,844 total
includes taxes & fees
2 Sept - 3 Sept
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A swimming pool with a waterfall feature surrounded by lush greenery.

18. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,518
HK$3,107 total
includes taxes & fees
23 Aug - 24 Aug
Waterfront Oasis of Annapolis Star
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

19. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (74 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is HK$2,604
HK$5,320 total
includes taxes & fees
14 Sept - 15 Sept
Charming Annapolis WaterVIEW Home
A calm lake with a sandy shore, surrounded by trees and houses.

20. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is HK$2,070
HK$6,069 total
includes taxes & fees
24 Aug - 25 Aug
Londontowne Home | Beach | 3BR
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Rooms where clean, staff was nice"
Debra 1-night trip
Posted 2 hours ago
Crowne Plaza Annapolis by IHG

Find out more about Deale

Search for holiday rentals in Deale on Expedia! You can easily find your home rentals, villas, holiday apartments in Deale using one of the methods below:

  • View our selection of featured holiday rentals in Deale
  • Use the map to find apartments and other holiday homes in the Deale neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Deale while they last

Look no further and take a look at our great range of rental properties in Deale!

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?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Deale is located near the beach, and has a fireplace, a balcony 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Deale?

Choose from 6 Expedia holiday rentals in Deale for a memorable holiday.

What’s there to see and do in Deale?

Northern Chesapeake Bay and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Parker Creek and Chesapeake Beach Water Park.

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.