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

Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
10.0 out of 10, Exceptional, (62)
"This is our second stay and it was just as memorable and lovely as our first stay. Pat and Ken are fantastic hosts. They think of everything! They are super responsive when you have questions/issues. They also let you know about things going on in the community so that you can join if you wish. The house itself is perfect for us. It's very well and generously stocked. Having a washer and dryer on site is a life saver when you travel by plane. I would highly recommend the Firefly Cottage if you...
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (188)
"Several family members and I went on a fishing trip out of Edgewater. We stayed in this wonderful cottage on the water. The house was immaculate and everything we needed aside from food was provided. The check in and check out were very simple and the host gave us contact information in case we needed anything. The location and overall property could not have been any better. We would definitely stay here again."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (106)
"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 can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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Waterfront home with beach mins to downtown boat or car Dog-Friendly
9.8 out of 10, Exceptional, (20)
"The home was beautiful, the setting was stunning, and the check-in and check-out process was a breeze! Our group of 6 cousins had a fantastic time together enjoying the beautiful views and all that Annapolis has to offer. We are already planning a return trip next year!"
Waterfront home with beach mins to downtown boat or car Dog-Friendly
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (155)
"Very nice home! It was decorated with many antiques and gave you a feeling of another time but with all the modern amenities for a wonderful time."
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
9.6 out of 10, Exceptional, (127)
"The house looked better than the pictures. It was very cozy and had everything we needed. It’s probably the best location for walking around town. Water pressure in the shower was decent, and the beds were comfortable."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
9.8 out of 10, Exceptional, (24)
"Appreciated the lovely waterfront location, independence , nice filtered water tap for drinking and coffee. Especially enjoyed meeting owner, delightful visit."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Artist, writer & creative minds stay where inspiration is free & serenity lives
Artist, writer & creative minds stay where inspiration is free & serenity lives
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (109)
"We had a wonderful trip to St. Michaels. This house is in the perfect location and has everything you need for a great stay!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (198)
"We love staying at Magee Cottage. It has all you need to relax and enjoy such a comfortable home on the water. This is our second stay and we’ll hurry back in a few months for more of the good life!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Relaxing and peaceful guest house close to beach towns and DC. Lotsa amenities.
10.0 out of 10, Exceptional, (34)
"Picked this property due to the location outside of the “city” and loved the rural location. The cottage fit our needs perfectly. Diana was very friendly and a wonderful host. The location was very peaceful."
The price is AED 514
AED 837 total
includes taxes & fees
23 Jun - 24 Jun
Relaxing and peaceful guest house close to beach towns and DC. Lotsa amenities.
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.8 out of 10, Exceptional, (18)
"Thoroughly enjoyed staying at this cozy cottage It was very clean, had lots of towels, comfortable beds with soft fluffy bedspreads. We also enjoyed sitting outside on the screened in porch when we weren't in the hot tub. The fact that it was in a gated community with lots of gorgeous flowers and trees it felt very private."
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Pet-friendly waterfront River Cottage for 2
8.6 out of 10, Excellent, (4)
"Beautiful views, private little cottage ideal for couples visiting with pets."
Pet-friendly waterfront River Cottage for 2
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
10.0 out of 10, Exceptional, (21)
"Exactly as advertised Great location Recommend coded integrated keyless entry be installed - eliminate bulky current lock box entry process Excellent property - would stay again"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (3)
"Beautiful location, great views, beautiful sun rises, view of working watermen Dogwood Harbour. Owner met us at the property with a bottle of wine — very friendly. Tilghman Island is a quaint and beautiful gem."
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (66)
"Jim was amazing and answered our questions, etc. almost immediately. He was wonderful and very accommodating. Cozy cottage, loved it."
Amazing views, short walks to great dining!
Updated North Beach Cottage: Pet Friendly!
9.8 out of 10, Exceptional, (9)
"This location was perfect for our trip for a wedding. Being only a three minute walk from the rehearsal, ceremony, and reception was absolutely perfect. Being close to the deli/market as well came in handy. The house was clean and welcoming. Overall I would absolutely stay here again."
Updated North Beach Cottage: Pet Friendly!
The Middle Point Cabin in Saint Michaels
9.8 out of 10, Exceptional, (47)
"Looked just like the pictures. Everything was new clean and comfortable. Enclosed patio was a hit with our cat."
The Middle Point Cabin in Saint Michaels
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (6)
"Great property, extremely clean and exactly as pictured on listing. Host was responsive and check in and check out was a breeze. Would recommend if you’re looking for a quiet weekend away at the Eastern shore!"
Eastern Shore Waterside Cottage Near St. Michaels
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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.

Other property types in Deale

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (75)
"The cottage provides a wonderful way to experience Deale and the surrounding area. Well equipped and clean, I had everything I needed and didn't want to leave,"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
9.8 out of 10, Exceptional, (6)
"The property was beautiful. The property manager was available for any inquiries we had. My family and I enjoyed it immensely. The view of the water was wonderful whether sitting on the dock or sitting in the sunroom. We played indoor and outdoor games. Perfect place for family bonding. The weather was perfect for our stay."
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Cozy place close to the city dock
10.0 out of 10, Exceptional, (55)
"We enjoyed our 2 nights at Cozy Place Close to the docks. Easy access and personalized connection with Nathalie were appreciated! We enjoyed the French and sail boating themes in the apartment, aligned the Annapolis maritime history! The docks are a short drive and old Town Annapolis was pleasant and historical! We recommend Cozy Place to others!"
Cozy place close to the city dock
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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