Search Vacation Homes in Chesapeake Beach

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chesapeake Beach vacation homes

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.0 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 ¥29,769
¥80,113 total
includes taxes & fees
May 20 - May 21
Family Beach House: Spacious Deck, Grill & Views

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (20 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 ¥10,930
¥48,239 total
includes taxes & fees
May 10 - May 11
Walk to Beach! King Bed & Free Beach Passes

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, (44 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 ¥27,154
¥58,678 total
includes taxes & fees
Jun 1 - Jun 2
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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, (14 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 ¥43,742
¥86,392 total
includes taxes & fees
May 10 - May 11
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is ¥30,003
¥79,929 total
includes taxes & fees
May 24 - May 25
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is ¥36,036
¥71,248 total
includes taxes & fees
May 20 - May 21
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is ¥37,603
¥73,075 total
includes taxes & fees
May 10 - May 11
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

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
9.0 out of 10, Wonderful, (7 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 ¥35,253
¥55,192 total
includes taxes & fees
May 10 - May 11
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (3 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is ¥38,387
¥78,159 total
includes taxes & fees
May 26 - May 27
Sunset Cottage - West River Access and Views!

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (44 reviews)
"The place was vey clean, whic is of upmost improtance to me. We loved the veiw and the location."
United States
Crystal H.
The price is ¥58,442
¥73,673 total
includes taxes & fees
May 27 - May 28
Sunset Breezes - quiet waterfront retreat

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, (14 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is ¥60,322
¥114,314 total
includes taxes & fees
Jun 1 - Jun 2
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
The price is ¥30,459
¥67,766 total
includes taxes & fees
May 11 - May 12
3-Bedroom Beach Home w/ Backyard

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 ¥32,433
¥56,136 total
includes taxes & fees
May 10 - May 11
Bright and airy waterfront getaway

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 ¥34,470
¥92,702 total
includes taxes & fees
May 26 - May 27
Annapolis Retreat - 7 mins from downtown Annapolis!

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Beach House w/TheaterRm, GameRm, Outdoor Shwr
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"This was a fantastic property and location for our stay in Lusby. The home is designed with families in mind, and there was plenty for everyone to do. The house is beautiful and in a quiet, residential community. You can walk to the beach less than two blocks away, and we found dozens of sharks teeth there! Josh was so helpful with advice throughout. We would definitely come again."
United States
Mollie O.
The price is ¥51,017
¥112,539 total
includes taxes & fees
May 17 - May 18
Beach House w/TheaterRm, GameRm, Outdoor Shwr

Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.0 out of 10, Wonderful, (8 reviews)
"This property was super gorgeous and spacious so we were able to relax. Guests had more than enough space and didn’t feel like they were on top of each other sleeping wise! We were able to just have dinner and feel safe! The owner answered any questions we had within 15 minutes, which was super helpful! "
United States
khaddija j.
The price is ¥52,880
¥104,940 total
includes taxes & fees
May 10 - May 11
Tranquil Modern Farmhouse

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 ¥38,230
¥108,955 total
includes taxes & fees
May 10 - May 11
Family Home on Mayo Peninsula | Deck | Sleeps 10

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.4 out of 10, Exceptional, (6 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is ¥33,059
¥89,486 total
includes taxes & fees
May 27 - May 28
Renovated Bungalow | Walk to Beach | Dog-Friendly

Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
10.0 out of 10, Exceptional, (2 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is ¥38,230
¥116,100 total
includes taxes & fees
May 10 - May 11
Londontowne Home | Beach | 3BR
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesapeake Beach Hotel Reviews

Find out more about Chesapeake Beach

Chesapeake Beach Vacation Homes information

Number of reviews
191
Accommodation
377 Vacation Homes
Lowest Price
¥48,239
Highest Price
¥116,100