A harbor with boats docked, a pier, and a row of houses along the water.

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Our top choices for Chesapeake Beach vacation homes

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is AED 1,025
AED 2,276 total
includes taxes & fees
5 Jul - 6 Jul
Family Beach House: Spacious Deck, Grill & 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, (47 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 500
AED 1,229 total
includes taxes & fees
6 Jul - 7 Jul
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (1 review)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is AED 436
AED 941 total
includes taxes & fees
14 Jul - 15 Jul
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is AED 559
AED 1,530 total
includes taxes & fees
12 Jul - 13 Jul
Walk to Beach! King Bed & Free Beach Passes

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home for a girls weekend away. The view is spectacular, host was communicative, and lots of thoughtful small touches throughout the home and the experience. Thank you for a wonderful stay! "
United States
Katie K.
The price is AED 1,183
AED 2,186 total
includes taxes & fees
6 Jul - 7 Jul
Sunset Cottage - West River Access and Views!

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 973
AED 2,416 total
includes taxes & fees
13 Jul - 14 Jul
Annapolis Retreat - 7 mins from downtown Annapolis!

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AED 889
AED 2,546 total
includes taxes & fees
5 Jul - 6 Jul
Family Home on Mayo Peninsula | Deck | Sleeps 10

Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AED 1,001
AED 1,705 total
includes taxes & fees
5 Jul - 6 Jul
Plum Point Cottage #17

Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
7.0 out of 10, Good, (2 reviews)
"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "
United States
rebekah h.
Londontowne Rancher | 3BR | Near Waterfront

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 AED 845
AED 1,406 total
includes taxes & fees
9 Jul - 10 Jul
Bright and airy waterfront getaway

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
The price is AED 307
AED 962 total
includes taxes & fees
5 Jul - 6 Jul
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

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, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AED 1,306
AED 2,540 total
includes taxes & fees
13 Jul - 14 Jul
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is AED 1,143
AED 1,466 total
includes taxes & fees
28 Jul - 29 Jul
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (12 reviews)
"Listing was accurate; communication with host was great and helpful. We had a wonderful family time."
United States
Melissa D.
The price is AED 1,102
AED 1,978 total
includes taxes & fees
5 Jul - 6 Jul
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (12 reviews)
"The home was lovely and very quiet location. My sister and I were caring for our mom after discharge from hospital and it was very convenient. Would stay there again. "
United States
Tova A.
The price is AED 1,697
AED 3,150 total
includes taxes & fees
7 Jul - 8 Jul
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (10 reviews)
"The host communicated immediately if needed. The house has practically everything a family needs. Fully stocked kitchen for meal prep, wonderful towels and memory foam beds. A wonderful rental."
United States
Kymme
The price is AED 1,488
AED 2,692 total
includes taxes & fees
7 Jul - 8 Jul
Tranquil Modern Farmhouse

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 1,458
AED 2,542 total
includes taxes & fees
7 Jul - 8 Jul
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, (71 reviews)
"We enjoyed our stay! The property has a beautiful view of the bay. It was a perfect set up for our family of four. "
United States
Jen M.
The price is AED 1,763
AED 3,199 total
includes taxes & fees
13 Jul - 14 Jul
Charming Annapolis WaterVIEW Home

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 AED 1,708
AED 4,197 total
includes taxes & fees
6 Jul - 7 Jul
Lakefront Cabin near Solomons Island w/ Hot Tub

Pet Friendly-newly built house in peaceful beach community, located in Riva MD.

Pet Friendly-newly built house in peaceful beach community, located in Riva MD.
Riva
10.0 out of 10, Exceptional, (3 reviews)
"The place was amazing!"
United States
Sonya N.
Pet Friendly-newly built house in peaceful beach community, located in Riva MD.
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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