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

Deale Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Deale vacation homes

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, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $136
CA $489 total
includes taxes & fees
Oct 4 - Oct 5
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

2. 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 CA $307
CA $710 total
includes taxes & fees
Oct 27 - Oct 28
3-bedroom house in Deale located on Bay many amenities and great views
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)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is CA $258
CA $734 total
includes taxes & fees
Oct 14 - Oct 15
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A deck with outdoor furniture, a red door, and a house with windows.

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
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is CA $246
CA $543 total
includes taxes & fees
Oct 26 - Oct 27
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A market with a covered seating area and a sign indicating parking for curbside pickup.

5. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (1 review)
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
The price is CA $319
CA $612 total
includes taxes & fees
Oct 1 - Oct 2
Rose Haven Coastal Cottage
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

6. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is CA $438
CA $822 total
includes taxes & fees
Oct 6 - Oct 7
Sunset Cottage - West River Access and Views!
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

7. 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 CA $408
CA $1,088 total
includes taxes & fees
Oct 4 - Oct 5
Family Home on Mayo Peninsula | Deck | Sleeps 10
Pool

8. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
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 CA $204
CA $649 total
includes taxes & fees
Oct 5 - Oct 6
Family Beach House: Spacious Deck, Grill & Views
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

9. 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, (55 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 CA $151
CA $438 total
includes taxes & fees
Oct 5 - Oct 6
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 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 CA $322
CA $857 total
includes taxes & fees
Oct 4 - Oct 5
Renovated Bungalow | Walk to Beach | Dog-Friendly
A beach with chairs and a pier in the background.

11. 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)
"Almost everything that you might need is provided, but if not there is shopping close by. Hot tub was nice. Very clean home."
United States
Sharon Z.
The price is CA $338
CA $760 total
includes taxes & fees
Oct 4 - Oct 5
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

12. 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 CA $302
CA $837 total
includes taxes & fees
Oct 20 - Oct 21
Annapolis Retreat - 7 mins from downtown Annapolis!
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

13. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (78 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 CA $549
CA $1,065 total
includes taxes & fees
Oct 1 - Oct 2
Charming Annapolis WaterVIEW Home
A spacious living room with a sofa set, a coffee table, and a chair. There is a painting on the wall and a window providing natural light.

14. Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
7.0 out of 10, Good, (2 reviews)
"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "
United States
rebekah h.
The price is CA $408
CA $1,071 total
includes taxes & fees
Oct 5 - Oct 6
Londontowne Rancher | 3BR | Near Waterfront
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

15. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $386
CA $655 total
includes taxes & fees
Oct 1 - Oct 2
Plum Point Cottage #17
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is CA $135
CA $420 total
includes taxes & fees
Oct 4 - Oct 5
Charming Coastal/Country Home w/3 Acres & Sauna!
A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

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

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is CA $349
CA $907 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
A wooden dock extending into a calm body of water with boats docked at the end.

18. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is CA $305
CA $612 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 2br home w/ parking in downtown Annapolis
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

19. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (22 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is CA $98
CA $301 total
includes taxes & fees
Oct 12 - Oct 13
Cute, Cozy 2-bedroom house near Annapolis with water access
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

20. Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.8 out of 10, Excellent, (12 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is CA $491
CA $725 total
includes taxes & fees
Oct 5 - Oct 6
Fabulous 5-bedroom house with AC in charming 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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Very clean"
John Frederick 2-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Deale

Deale Vacation Homes information

Number of reviews
312
Accommodation
585 Vacation Homes
Lowest Price
CA $301
Highest Price
CA $1,088

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