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Compare 55 Cottages in Deale with updated reviews, rates, and availability.

Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
10.0 out of 10, Exceptional, (75)
"Lovely house and location! Pat and Ken were rapid and personable with every interaction."
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Cottage on a quite creek of the Chesapeake Bay with private pool.
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (211)
"The cottage is beautiful and comfy on the inside. We enjoyed the screened porch where I sat for hours reading my book. I must admit it was my first time being in a place where there are no streetlights, and the dark of night is so beautiful. I can never see the stars in the city. A gem. My mother, husband and I really enjoyed our stay. "
Relaxing Waterfront Cottage Near St Michaels, Maryland
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Living room
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
10.0 out of 10, Exceptional, (38)
"My sister and I came back for the 2nd year in a row. We love your property. Itā€™s got everything we needed. A nice pool and gazebo with a stunning view. "
The price is SARĀ 499
SARĀ 1,062 total
includes taxes & fees
23 Sep - 24 Sep
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (148)
"This was just a super place- right in the water and beautifulā€¦ and surprisingly spacious for a cottage. I loved the kitchen farm sink and the sun coming in the morning off the bay. Will definitely love to stay again. The owner was so nice and thought of all the little details!! Thank you!!"
The Yellow Cottage on Harness Creek
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Front of house from St. Michaels harbor looking across Town Park
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (107)
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we canā€™t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Eastern Shore Waterside Cottage Near St. Michaels
wrap around porch with rockers and dining area
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (18)
"We had a great stay at this house. We enjoyed using the kayak and paddleboard. (Access to the water is across this street.) We also enjoyed the pool and relaxing on the porch. It was about a 15 minute drive into St Michaelā€™s, where we had excellent meals, went sailing, and enjoyed the cute shops and pretty houses. It was a really nice, relaxing weekend! "
Eastern Shore Waterside Cottage Near St. Michaels
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Blue heron sunset
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (5)
"Our stay was amazing! Words cannot say enough! The view is magical. We enjoyed coffee on the porch to watch the sunrise and the crab/oyster boats going in and out. Maria, is a wonderful and very thoughtful host. At her recommendation, we went to the free wine tasting at the General Store at the end of the street. We met several local residents who could not be more kind and fun to talk with. We can't wait to come back and stay again."
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
Exterior
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
10.0 out of 10, Exceptional, (1)
"If you want to get away from it all, this is the place to be. My wife and I celebrated our 20th wedding Anniversary. Calm and peaceful, nestled right by the Choptank River. The cottage itself was very comfortable. The air conditioner worked great. It was a pleasure staying there and we will probably return next year."
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (199)
"What a lovely hideaway!!! The owners are extremely hospitable and the area is beautiful quaint and close to everything. Thank you for having us!!!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Amazing views, short walks to great dining!
"The design is probably my favorite thing about the placeā€”itā€™s well thought out and has an excellent flow. I also slept very deeply. Canā€™t wait to return." Melissa - April 2021
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (71)
"Our stay at this Vrbo in Annapolis was nothing short of spectacular! The property is beautifully maintained, offering the perfect blend of comfort and style. The attention to detail was evident, from the cozy living spaces to the well-appointed kitchen that had everything we needed for our stay. The location is unbeatableā€”close enough to all the attractions, restaurants, and shops make Annapolis the charming city that it is (1.2 miles walk to the Naval Academy), while distanced enough to be a...
Amazing views, short walks to great dining!
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Front of Carpenter St. Cottage
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (165)
"Great little cottage and plenty of space for our family of 3 to have an end-of-Summer getaway to one of our favorite towns. Prompt and easy communication with the owner, Tom, both before and during our stay. We loved the back porch and were blessed with some cooler temps and were able to enjoy sitting out there. FYI - Den has a door (third bedroom with pull out sofa). We have rented on Carpenter Street before, and the location cannot be beat as far as walkability to everything in town and along...
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Front and side view of Blades House from Locust St.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (130)
"Had a wonderful time. This home was just perfect for us. Great location and charming. Would definitely stay here again"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Eastport Cozy Charmer
Living area
Eastport Cozy Charmer
9.4 out of 10, Exceptional, (3)
"We really enjoyed our stay. We felt very comfortable there, and it worked well for us. Especially liked that there was space to park the boat on the street next to the house."
Eastport Cozy Charmer
Pet-friendly Annapolis Home: Walk to Beach!
Property grounds
Pet-friendly Annapolis Home: Walk to Beach!
3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
Enchanting West River Retreat
View from property
Enchanting West River Retreat
10.0 out of 10, Exceptional, (5)
"The views are spectacular and the boat dock is lovely..the hospitality was amazing too canā€™t wait to come back and visit "
Enchanting West River Retreat
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Front and side of W Melson House
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (113)
"We love escaping to St Michaels for a change of scenery. These historic properties are great places to disconnect from our normal fast paced lifestyle. We always enjoy that our dogs are able to enjoy our stay. Itā€™s a vacation for them as well. The town is very dog friendly in general. The properties are historic and have their quirks. For us, this adds to the experience and charm of St Michaels. The centralized location is key. "
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Updated North Beach Cottage: Pet Friendly!
North Beach Vacation Rental | 3BR | 2BA | 1,440 Sq Ft | Stairs Required to Enter
Updated North Beach Cottage: Pet Friendly!
9.8 out of 10, Exceptional, (10)
"We had a great time. Nice place. Within walking distance to small deli/ market. Just wished we wouldn't have had to pay to go to the beach."
Updated North Beach Cottage: Pet Friendly!
The Middle Point Cabin in Saint Michaels
Living area
The Middle Point Cabin in Saint Michaels
9.8 out of 10, Exceptional, (48)
"nice property. secluded. clean and comfortable. owners very very responsive. "
The Middle Point Cabin in Saint Michaels
Waterfront River Cottage for 2, dog-friendly
Welcome to the waterfront cozy River Cottage!
Waterfront River Cottage for 2, dog-friendly
8.8 out of 10, Excellent, (5)
"Itā€™s a wonderful place. Ideal for sleeping one or two. I hosted 10 of my family for a crab roll feed down by the water. It was delightful and I was glad to get back in the kitchen after seven days on I-90 and fast food."
Waterfront River Cottage for 2, dog-friendly
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Exterior
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
9.8 out of 10, Exceptional, (31)
"We had a great stay in this quiet beautiful house. Annapolis was close by and a fun time."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
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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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Other property types in Deale

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Grill no longer works
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (83)
"The house was clean and comfortable. Walking distance to a local restaurant. Screened porch was great for watching the sunrise in the morning and the boats coming in and out of harbor "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
10.0 out of 10, Exceptional, (75)
"Lovely house and location! Pat and Ken were rapid and personable with every interaction."
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Private Pier
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (15)
"We stayed at this beautiful property for my 50th birthday Girls trip. We were 15 of us. The house is very spacious, attractive pool and water facing sun room. Some of the rooms have gorgeous views of the water. They have a pickleball court, large family room where we could all hang out together"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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.

Frequently asked questions

How much do cottages in Deale cost?
Prices for cottages in Deale range between SAR249 and SAR249 per night. No matter your budget, youā€™re sure to find a perfect place to reconnect with nature. This price was 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?
Expedia has some superb cottages in Deale, so get ready for an unforgettable vacation on natureā€™s doorstep. If you have a certain budget, click on how much youā€™d like to spend and the preferred star rating of your property. Or, make your way to the filters to search for cottages with a hot tub or a kitchen. Weā€™ll help you find the perfect pad whatever your style of travel or plans.
How can I find cheap cottages in Deale?
With Expediaā€™s useful filter tool, locating cheap cottages in Deale has never been easier. To discover stays that are very pocket friendly, narrow down your search by star rating, budget and amenities.