Aerial view of Annapolis capital city of Maryland state with expensive waterside properties along the Chesapeake Bay, state capital building and naval academy, dreamy blue sky

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Our top choices for Shady Side vacation homes

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 1,043
AED 2,017 total
includes taxes & fees
16 Jun - 17 Jun
Sunset Cottage - West River Access and Views!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is AED 324
AED 1,035 total
includes taxes & fees
15 Jun - 16 Jun
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (14 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is AED 918
AED 1,538 total
includes taxes & fees
15 Jun - 16 Jun
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (36 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is AED 615
AED 1,329 total
includes taxes & fees
21 Jun - 22 Jun
Charming Coastal/Country Home w/3 Acres & Sauna!

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"Just was very responsive to all requests and inquiries."
United States
Vesta M.
The price is AED 463
AED 1,164 total
includes taxes & fees
15 Jun - 16 Jun
Large 2 bedroom house with private parking in a nice neighborhood

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (21 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is AED 681
AED 1,649 total
includes taxes & fees
30 Jun - 1 Jul
Walk to Beach! King Bed & Free Beach Passes

Cute, Cozy 2-bedroom house in near Annapolis with water access

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
9.4 out of 10, Exceptional, (9 reviews)
"Host was wonderful! Enjoyed our weekend in a very clean, comfortable and peaceful place. Look forward to returning in warmer weather."
United States
Katherine P.
The price is AED 314
AED 852 total
includes taxes & fees
14 Jun - 15 Jun
Cute, Cozy 2-bedroom house in near Annapolis with water access

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Edgewater
8.6 out of 10, Excellent, (9 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is AED 826
AED 1,315 total
includes taxes & fees
17 Jun - 18 Jun
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AED 918
AED 2,328 total
includes taxes & fees
13 Jul - 14 Jul
Annapolis Retreat - 7 mins from downtown Annapolis!

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (15 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is AED 1,098
AED 2,118 total
includes taxes & fees
16 Jun - 17 Jun
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The host was very welcoming and responsive before and during the stay for my questions. The house was clean and comfortable. The hot tub was lovely for a soak. We enjoyed the walk to and sitting on the peaceful community beach. Thank you!"
United States
Kathy S.
The price is AED 992
AED 2,190 total
includes taxes & fees
15 Jun - 16 Jun
Charming Annapolis WaterVIEW Home

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (36 reviews)
"Everything was as expected, lovely spot even with lots of snow and ice!"
United States
Becky S.
The price is AED 685
AED 1,896 total
includes taxes & fees
17 Jun - 18 Jun
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AED 970
AED 2,651 total
includes taxes & fees
21 Jun - 22 Jun
Family Home on Mayo Peninsula | Deck | Sleeps 10

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (7 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is AED 768
AED 2,127 total
includes taxes & fees
18 Jun - 19 Jun
Renovated Bungalow | Walk to Beach | Dog-Friendly

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (15 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AED 1,388
AED 2,646 total
includes taxes & fees
15 Jun - 16 Jun
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is AED 889
AED 2,546 total
includes taxes & fees
14 Jun - 15 Jun
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is AED 1,104
AED 1,422 total
includes taxes & fees
15 Jun - 16 Jun
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is AED 327
AED 1,248 total
includes taxes & fees
15 Jun - 16 Jun
3-bedroom house in Deale located on Bay many amenities and great views

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is AED 1,047
AED 2,285 total
includes taxes & fees
13 Jul - 14 Jul
Family Beach House: Spacious Deck, Grill & Views

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Cape Saint Claire
9.0 out of 10, Wonderful, (13 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
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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