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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
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In three months
Nov 14 - Nov 16

Cottages in Deale

6 Mi to Dtwn: Family-friendly Home in Annapolis!
Interior

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
House (3 Bedrooms) | Interior

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Interior

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
8.0 out of 10, Very Good, (2)
"The water is well water and it stinks, water treatment could improve that. This is more in the woods than beachy. In a rundown area. Get some Damprid to cut down on musty smell. Cute decor."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Waterfront North Beach Home ~ 2 Mi to Beach!
House (2 Bedrooms) | Interior

Waterfront North Beach Home ~ 2 Mi to Beach!

3.0 star property
Waterfront North Beach Home ~ 2 Mi to Beach!
Tilghman Island Retreat By Knapps Narrows!
House (2 Bedrooms) | Interior

Tilghman Island Retreat By Knapps Narrows!

3.0 star property
Tilghman Island Retreat By Knapps Narrows!
Waterfront Annapolis Home: Fire Pit & Fishing Pier
House (3 Bedrooms) | Interior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Updated North Beach Cottage: Pet Friendly!
Cottage (3 Bedrooms) | Interior

Updated North Beach Cottage: Pet Friendly!

3.0 star property
6.0 out of 10, (1)
"The property needs a severe cleaning. The floors were filthy. "
Updated North Beach Cottage: Pet Friendly!
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Outdoor spa tub

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

3.0 star property
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Annapolis Home Near Beach & Quiet Waters Park!
Interior

Annapolis Home Near Beach & Quiet Waters Park!

3.0 star property
Annapolis Home Near Beach & Quiet Waters Park!
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Exterior

Bayfront Maryland Retreat w/ Deck, Near Beaches!

3.0 star property
Bayfront Maryland Retreat w/ Deck, Near Beaches!
North Beach Cottage - Walk to Chesapeake Bay
Cottage (3 Bedrooms) | Interior

North Beach Cottage - Walk to Chesapeake Bay

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house condition was very cleran,beautiful. we appreciate the house owner's guidance&help. we made very good memories!"
North Beach Cottage - Walk to Chesapeake Bay
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Outdoor dining

Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit

3.0 star property
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Waterfront Home w/ Hot Tub in Bozman Village!
House (4 Bedrooms) | Interior

Waterfront Home w/ Hot Tub in Bozman Village!

3.0 star property
Waterfront Home w/ Hot Tub in Bozman Village!
Water-view Deale Home: Walk to Marina, Restaurants
House (5 Bedrooms) | Interior

Water-view Deale Home: Walk to Marina, Restaurants

3.0 star property
Water-view Deale Home: Walk to Marina, Restaurants
Coastal Edgewater Home w/ Private Hot Tub!
Interior

Coastal Edgewater Home w/ Private Hot Tub!

3.0 star property
Coastal Edgewater Home w/ Private Hot Tub!
Walk to Lake & Boat Ramp: Central Gem in Annapolis
House (4 Bedrooms) | Interior

Walk to Lake & Boat Ramp: Central Gem in Annapolis

3.0 star property
Walk to Lake & Boat Ramp: Central Gem in Annapolis
13 Mi to Annapolis: Dog-friendly Home w/ Fire Pit!
House (3 Bedrooms) | Interior

13 Mi to Annapolis: Dog-friendly Home w/ Fire Pit!

3.0 star property
13 Mi to Annapolis: Dog-friendly Home w/ Fire Pit!
Waterfront St Michaels Vacation Rental w/ Fire Pit
Microwave, oven, stovetop, dishwasher

Waterfront St Michaels Vacation Rental w/ Fire Pit

3.0 star property
Waterfront St Michaels Vacation Rental w/ Fire Pit
Coastal Pet-friendly Cottage <½ Mi to Beaches
Exterior

Coastal Pet-friendly Cottage <½ Mi to Beaches

3.0 star property
Coastal Pet-friendly Cottage <½ Mi to Beaches
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"I just had the best birthday here. Perfect location, staff was amazing. "
julio 2-night trip
Posted 1 day ago
Historic Inns of Annapolis

Frequently asked questions

How much do cottages in Deale cost?
Cottages in Deale range between and per night. These stays offer a chance to get in touch with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Deale with Expedia?
We think that a vacay should be easy, so if you're seeking cottages in Deale at an affordable rate, Expedia has got your back. Save cash and check in to a thrifty option surrounded by wilderness, or splurge on a 5-star cottage to really spoil your favorite people.
How can I find cheap cottages in Deale?
Expedia can help you easily track down cheap cottages in Deale. To find a superb stay in just a few clicks, try out the filter tool to tailor your search results by budget, amenities and star rating.