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Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

Compare 64 Cottages in Deale with updated reviews, rates, and availability.

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (173)
"Great location! Antique furniture in a well maintained beautiful old house. Exactly what we needed."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (220)
"This was a winter getaway to a very comfortable house with all the amenities on a quiet tributary of the Chesapeake. A rare vacation for and just what we wanted. Conveniently located near St Michael’s and Easton. Communication was excellent and everything was just as described. Would go back if we get the opportunity. "
Relaxing Waterfront Cottage Near St Michaels, Maryland
Secluded Cozy Cottage in Historic Downtown
Terrace/patio

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (7)
"Such a wonderful experience staying in this poperty for a couple of days. Walking distance to everything. Jennifer was a pleasure and very responsive. May make this an annual visit! Loved Annapolis!"
The price is SAR 1,500
SAR 2,540 total
includes taxes & fees
10 Mar - 11 Mar
Secluded Cozy Cottage in Historic Downtown
Eastern Shore Waterside Cottage Near St. Michaels
Outdoor dining

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

9.6 out of 10, Exceptional, (136)
"The T. Blades house was the perfect choice for a two day quick getaway for my husband and I. The house is not only filled with period charm and character, but has been lovingly and perfectly restored to make it a very comfortable stay. Immaculately clean and furnished. The location is a 5 star, as well. One block to the main street with shops and restaurants, and two blocks in the other direction to the water. Can't wait to go back. Kathleen and John"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (207)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Terrace/patio

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

10.0 out of 10, Exceptional, (26)
"Amazing house! perfect for my family and our stay in Annapolis. Perfect location to everything. We had all of the amenities we needed and everything was easy to use. If I had one thing negative to say, I wish I could have had my dogs with us, I would have gladly paid a cleaning fee to have them there. Luckily I was able to make other arrangements. Thank you for sharing your house with my family!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
North Beach Cottage - Walk to Chesapeake Bay
Interior

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (30)
"Our family was in town to attend the promotion in the air force of a nephew at Ft. McNair. Close to everything. Beautiful house prefect for us. Enjoyed walking the boardwalk. Would highly recommend this property. Excellent communication with the host. "
North Beach Cottage - Walk to Chesapeake Bay
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Property grounds

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

9.8 out of 10, Exceptional, (22)
"My husband and I stayed here for 3 nights while I recovered from a surgery. It was a perfect, peaceful cottage and beautiful neighborhood. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Charming Waterfront Cottage Retreat near St. Michaels
Fridge, microwave, oven, stovetop

Charming Waterfront Cottage Retreat near St. Michaels

10.0 out of 10, Exceptional, (1)
"Our stay at this beautiful cottage was truly unforgettable! The space was clean, cozy, and well-appointed, with every detail carefully considered. Nestled right on the water’s edge, every inch of the house was tastefully decorated and had all the amenities you could ask for. The tasteful decor, fully stocked kitchen, and comfortable bed made us feel right at home from the moment we arrived.The hosts went above and beyond to make this an enjoyable stay, with excellent communication and thoughtful...
Charming Waterfront Cottage Retreat near St. Michaels
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Miscellaneous

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (8)
"The home was so well appointed and walking distance to stores, restaurants, quaint museums and beautiful nature. The host was so friendly and helpful with quick responses. We had high winds and lots of rain, but stayed cozy and warm. What a friendly Island of people!!"
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
On the beach, sun loungers, beach towels

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

9.8 out of 10, Exceptional, (29)
"My stay was wonderful, listing just as described. Beautiful water views and enjoyed the local area. Highly recommend and plan to return. Thank you so much for a lovely stay!"
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break
Exterior

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break

10.0 out of 10, Exceptional, (85)
"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break
Waterfront River Cottage for 2, dog-friendly
On the beach

Waterfront River Cottage for 2, dog-friendly

9.2 out of 10, Wonderful, (7)
"It's a beautiful location and we enjoyed our visit."
Waterfront River Cottage for 2, dog-friendly
Enchanting West River Retreat
Outdoor dining

Enchanting West River Retreat

10.0 out of 10, Exceptional, (8)
"Trip from Denver to see our son at the academy. Place was all that was advertised - clean, well appointed, comfortable, nice neighborhood. Its not far from the academy in terms of miles but you have to travel a lot of backroads to get there. We enjoyed our stay and would stay here again. "
Enchanting West River Retreat
Pet-friendly Annapolis Home: Walk to Beach!
Interior

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
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!
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Smart TV, fireplace, books, printers

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
The price is SAR 1,572
SAR 3,415 total
includes taxes & fees
11 Mar - 12 Mar
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (113)
"The location couldn't have been more ideal. We were able to walk everywhere...all around town. And there was a beautiful view of the town park and the bay from the house. We were there for Christmas, visiting family, and her house was overflowing, so this was a little home-away-from-home. There were some difficulties. The shower curtain and main bath downstairs needs updating and the kitchen could be better appointed. The stairs to the king bed bedroom are, as others and the owner noted, very...
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (117)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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
View from property

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (87)
"This lovely home sets in a beautful location. The hosts are available and accommodating. They are definitely available if needed. The house itself is very comfy. All amenities you need are there. "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Million Dollar View of the Chesapeake Bay
Dining

Million Dollar View of the Chesapeake Bay

9.8 out of 10, Exceptional, (118)
"It’s hard to give a full review when everything was great! But the house is beautiful, cozy and very well-cared for. It was the perfect option for a quiet weekend family getaway. "
Million Dollar View of the Chesapeake Bay
Chesapeake Houseboat Getaway on Kent Island, Maryland
Marina

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.6 out of 10, Exceptional, (20)
"We had a wonderful stay on this luxurious houseboat! Clean, comfortable & fun and Julia is an excellent host. We highly recommend Julia's Arc!"
Chesapeake Houseboat Getaway on Kent Island, Maryland
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?
Cottages in Deale range between SAR 1,500 and SAR 1,572 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.