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Compare 527 Vacation Homes in Deale with updated reviews, rates, and availability.

Sweet Bamboo Beach Cottage

9.8 out of 10, Exceptional, (70)
"Couldn’t be happier with our stay. The house was exactly as pictured. Neighborhood was quiet with a small town feel. Most of the major appliances appeared relatively new, the beds were comfortable and the house was staffed with an abundance of linens and towels. Front and back yards are completely fenced in which is perfect for those with small dogs. North Beach is only a short drive from College Park, Baltimore and Annapolis. Check in was a breeze. Would definitely consider staying there...
Sweet Bamboo Beach Cottage

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (49)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (207)
"We loved our stay here! The location is unbeatable and having access to parking was very convenient. The house itself was quaint with character and very clean! My husband and I stayed with our 4 young children and had ample space. The beds were all comfy and the kitchen had everything we needed. Communication with the host was great! We really hope to stay here again in the future! "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.8 out of 10, Exceptional, (68)
"This is a great location The house is clean and updated. We enjoyed and would stay here again."
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (104)
"Great location. "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub

9.6 out of 10, Exceptional, (24)
"The property is beautiful. The house is spacious and has comfortable beds and excellent bathrooms. There were some things that could make a stay so much better. The bedrooms need at least one chair. Although there were books in a drawer with directions for the high end appliances, each one should have a quick explanation on usage next to it. The information said the table seated 8 and yet there were only six chairs! A putting green was described and even showed a picture of one in the original...
Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub

Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD

Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD

Historic Home with Parking Steps From Capital & USNA

9.6 out of 10, Exceptional, (9)
"What a cute, historic row house that is about five or six houses down from the Maryland State house and a few blocks up from the docks and the Naval Academy entrance. The bonus is there is a parking space--just leave your car and walk to all of downtown Annapolis. Bathroom & kitchen are practically brand new. Very clean, very comfortable, and allowed us to wander the shops, museums, and food around town. "
Historic Home with Parking Steps From Capital & USNA

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (43)
"Would stay again."
The Lazy Crab Beach House - Free beach passes

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

Time Stands Still At the Dock.

10.0 out of 10, Exceptional, (2)
"What a wonderful experience! A relaxing time with an amazing view! Thank you Jennifer"
Time Stands Still At the Dock.

7 mins away from Downtown Annapolis

9.8 out of 10, Exceptional, (16)
"Loved the house, we were glad to be able to book it on short notice for a large group! Beds were insanely comfortable, and the house had everything we needed. It was clean, comfortable, and a fantastic location. Only downside is that the common areas (living room/kitchen/dining area) are a bit small if you have a larger group (8). Overall a great stay and would stay again!!"
7 mins away from Downtown Annapolis

Charming garden row home, easy 4 block walk to the heart of Annapolis.

10.0 out of 10, Exceptional, (109)
"I visited my midshipman and I couldn’t have asked for a better place! Very comfortable & spacious-yet not too big. It was as if we were home. Location was awesome. Mike was great with immediate communication-especially in preparing us with info well before our check in day! I would definitely stay here again! "
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Your Annapolis Adventure Starts Here!!

10.0 out of 10, Exceptional, (138)
"We enjoyed our stay as much as the 1st time. Great spot for an Annapolis getaway! House is comfortable and location is ideal. Gracious and responsive host."
Your Annapolis Adventure Starts Here!!

25-50% Off~Private Beach~Hot Tub~Fire Table~

9.8 out of 10, Exceptional, (20)
"So peaceful just so relaxing . So organized thank you"
25-50% Off~Private Beach~Hot Tub~Fire Table~

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2.0 star property
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

MODERN 2022 NEWLY BUILT TOWNHOME

10.0 out of 10, Exceptional, (9)
"This place was perfect for out boat show week!"
MODERN 2022 NEWLY BUILT TOWNHOME

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

10.0 out of 10, Exceptional, (23)
"Great place and location. Not far from good food and local hot spots. Would definitely rebook and stay here again. "
The price is AED 270
AED 909 total
includes taxes & fees
9 Mar - 10 Mar
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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
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

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

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

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.