Aerial view of Chesapeake Beach marina with luxury sail boats, beach house apartments, fishing boats near the water park popular vacation spot for Washington residents in Calvery county Maryland

Holiday Homes in Chesapeake Beach

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Our top choices for Chesapeake Beach holiday homes

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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 AU$893
includes taxes & fees
13 July - 14 July
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

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 AU$390
includes taxes & fees
15 June - 16 June
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 AU$508
includes taxes & fees
14 June - 15 June
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

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 AU$590
includes taxes & fees
24 June - 25 June
Walk to Beach! King Bed & Free Beach Passes

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 AU$895
includes taxes & fees
13 July - 14 July
Annapolis Retreat - 7 mins from downtown Annapolis!

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The view was incredible! So magical. My daughters and I watched the sunrise over the bay every morning from the living room. On our last morning there was a family of deer grazing as we watched - it was so beautiful! The master bathroom is amazing. It was the perfect spot for family to gather for brunch before a wedding! "
United States
Lia D.
The price is AU$852
includes taxes & fees
14 June - 15 June
Charming Annapolis WaterVIEW Home

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (20 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is AU$506
includes taxes & fees
14 June - 15 June
Bright and airy waterfront getaway

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 AU$733
includes taxes & fees
14 June - 15 June
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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 AU$784
includes taxes & fees
16 June - 17 June
Sunset Cottage - West River Access and Views!

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 AU$827
includes taxes & fees
18 June - 19 June
Renovated Bungalow | Walk to Beach | Dog-Friendly

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 AU$1,021
includes taxes & fees
14 June - 15 June
Family Home on Mayo Peninsula | Deck | Sleeps 10

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is AU$550
includes taxes & fees
15 June - 16 June
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 AU$507
includes taxes & fees
24 June - 25 June
3-bedroom house in Deale located on Bay many amenities and great views

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 AU$1,020
includes taxes & fees
15 June - 16 June
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Lakefront Cabin near Solomons Island w/ Hot Tub

Lakefront Cabin near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (1 review)
"We had such a wonderful stay at Diana’s lake house! The view of the lake is absolutely beautiful waking up to that peaceful scenery every morning was one of the highlights of our trip.The property has a charming rustic feel while still offering all the amenities you could need. It felt cozy and comfortable, yet fully equipped for a relaxing getaway. We especially loved being able to kayak right from the area such a perfect way to enjoy the water and the surroundings.Diana was an exceptional...
United States
rakesh s.
The price is AU$1,470
includes taxes & fees
10 July - 11 July
Lakefront Cabin near Solomons Island w/ Hot Tub

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
The price is AU$793
includes taxes & fees
15 June - 16 June
3-Bedroom Beach Home w/ Backyard

Secluded Woodland Waterfront Retreat

Secluded Woodland Waterfront Retreat
Solomons
10.0 out of 10, Exceptional, (12 reviews)
"The host was very communicative, the house was very clean and comfortable, and the river views were beautiful!"
United States
Meghan H.
The price is AU$811
includes taxes & fees
15 June - 16 June
Secluded Woodland Waterfront Retreat

Franklin At The Bay

Franklin At The Bay
Deale
10.0 out of 10, Exceptional, (1 review)
"This place is beautiful, and big. The back yard is nice. We played games out back and had a cookout. Walking distance to the pier and a playground. The"
United States
Jamie C.
The price is AU$911
includes taxes & fees
7 July - 8 July
Franklin At The Bay

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (44 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is AU$829
includes taxes & fees
13 July - 14 July
Sunset Breezes - quiet waterfront retreat

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 AU$854
includes taxes & fees
17 June - 18 June
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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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Top Chesapeake Beach Hotel Reviews

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Chesapeake Beach Holiday Homes information

Number of reviews
282
Accommodation
410 Holiday Homes
Lowest Price
AU$390
Highest Price
AU$1,470