Deale Holiday Homes from €203: Search Top House Rentals

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

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Our top choices for Deale holiday 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

North Beach

Johanna S.

includes taxes & fees

13 Sept - 14 Sept

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

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

North Beach

Penny N.

includes taxes & fees

16 Sept - 17 Sept

A deck with outdoor furniture, a red door, and a house with windows.

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

Shady Side

Joshua T.

includes taxes & fees

21 Sept - 22 Sept

A living room with a sofa, coffee table, fireplace, and artwork on the wall.

4. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

5. Sunset Cottage - West River Access and Views!

Shady Side

Marci M.

includes taxes & fees

9 Sept - 10 Sept

A laundry room with a washing machine and dryer, wooden cabinets above, and a shelf with a bottle.

6. Rose Haven Coastal Cottage

North Beach

includes taxes & fees

20 Sept - 21 Sept

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

Chesapeak beach

Bryan P.

includes taxes & fees

8 Sept - 9 Sept

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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

Stevensville

Dawn G.

includes taxes & fees

16 Sept - 17 Sept

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Pamela B.

includes taxes & fees

9 Sept - 10 Sept

A bedroom with a sloped ceiling, a bed with a striped bedspread, two red chairs, a television mounted on the wall, and a window with blinds.

10. Annapolis Charmer - Perfect Location

Historic District

includes taxes & fees

8 Sept - 9 Sept

A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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

Edgewater

Kristin G.

includes taxes & fees

8 Sept - 9 Sept

A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

12. Plum Point Cottage #17

Huntingtown

includes taxes & fees

19 Sept - 20 Sept

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

13. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

includes taxes & fees

15 Sept - 16 Sept

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

Edgewater

Diane D.

A lighthouse with a white exterior, a balcony, and a metal roof.

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

Stevensville

Michelle P.

includes taxes & fees

17 Sept - 18 Sept

A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

16. Charming Annapolis WaterVIEW Home

Arundel on the Bay

Whitney M.

A calm lake with a sandy shore, surrounded by trees and houses.

17. Londontowne Home | Beach | 3BR

Edgewater

Sam A.

includes taxes & fees

8 Sept - 9 Sept

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.

18. Londontowne Rancher | 3BR | Near Waterfront

Edgewater

"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. "

rebekah h.

includes taxes & fees

14 Sept - 15 Sept

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

Herald Harbor

Taylor C.

includes taxes & fees

8 Sept - 9 Sept

A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

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

Annapolis

includes taxes & fees

9 Sept - 10 Sept

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Top Deale Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Everything was fine . I have no complaints . Loved free parking ."

Historic Inns of Annapolis

8/10 Good

"Fantastic location. Clean room with comfortable beds and powerful AC. Liked the history of the building. We were able to consistently get parking on the street near the hotel, which was great. The only real con was that we discovered upon reaching our room that we didn't have an exterior window--our two "windows" looked over the covered event area, which had pretty lights but was nonetheless an interior hallway, so no outside view. There were also a couple hiccups with the bathroom, one being that the glass shelf was falling down, and the other being that we were consistently given two towels even though we had four people on the reservation. But overall we were happy with our stay and appreciated being in a historic building in such a great location."

Anchored Inn at Hidden Harbour Marina

8/10 Good

"I really like this place. Second time staying here, the night before a charter fishing trip. It’s a cozy independently run hotel that has a super popular outdoor bar in the front. The bar closes at 830 so no worries there with noise. It’s a fun environment to hang out and relax. I only wish there were more tables and chairs away from that area to enjoy the water view (there are a few but they fill up quick) When the bar closes it’s pretty much lights out, so it would be cool to have an area just for hotel guests. The room is clean and comfortable, the pillows are super small for some reason. I would definitely stay here again if I’m in the area."

Sonesta ES Suites Annapolis

8/10 Good

"Ver nice older hotel but well maintained. Spacious rooms and good breakfast. My only complaint is that you can tell they also keep long term tenants as there were cats roaming around (which didn’t bother me but might others) and bikes/trash outside some of the rooms and plants in windows. A normal nightly rental hotel would not allow this id think so it made the atmosphere seem a lil run down even if the room was decent."

Find out more about Deale

Deale Holiday Homes information

Number of reviews	126
Accommodation	585 Holiday Homes
Lowest Price	€203
Highest Price	€662

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Deale holiday homes

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

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

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

4. 3-bedroom house in Deale located on Bay many amenities and great views