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Vacation Homes in Chesapeake Beach

Family Beach House: Spacious Deck, Grill & Views

Chesapeake Beach
9.0 out of 10, Wonderful, (6)
"This house could not have a better location. There’s a gorgeous beach right across the street. My family and I spent many hours walking the beach looking for beach glass and shark teeth, which were surprisingly plentiful. There was even a nice dock to fish on. The house is very well kept. The upstairs table on the patio was a favorite of mine. The owner was in constant contact. We had a blast."
United States
Jeff B.
The price is AED 522
AED 1,485 total
includes taxes & fees
15 Dec - 16 Dec
Family Beach House: Spacious Deck, Grill & Views

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
The price is AED 251
AED 920 total
includes taxes & fees
18 Nov - 19 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview

Walk to Beach! King Bed & Free Beach Passes

North Beach
10.0 out of 10, Exceptional, (16)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is AED 361
AED 1,263 total
includes taxes & fees
16 Nov - 17 Nov
Walk to Beach! King Bed & Free Beach Passes

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Shady Side
10.0 out of 10, Exceptional, (4)
"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "
United States
Mark E.
The price is AED 529
AED 1,566 total
includes taxes & fees
16 Nov - 17 Nov
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Beautiful Waterfront Retreat in Cambridge!

Cambridge
10.0 out of 10, Exceptional, (49)
"Wonderful stay. The Crab Shack and dock were the highlights. We spent most of our time there. It was awesome. Highly recommend. "
United States
Christopher D.
The price is AED 661
AED 1,468 total
includes taxes & fees
17 Nov - 18 Nov
Beautiful Waterfront Retreat in Cambridge!

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

Arundel on the Bay
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is AED 777
AED 1,840 total
includes taxes & fees
19 Nov - 20 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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

Prince Frederick
9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is AED 606
AED 1,273 total
includes taxes & fees
24 Nov - 25 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere
10.0 out of 10, Exceptional, (4)
"Property was perfect for my regatta crew. Loved it."
United States
Michael Q.
The price is AED 680
AED 2,035 total
includes taxes & fees
1 Dec - 2 Dec
Annapolis Retreat - 7 mins from downtown Annapolis!

Wright's Cottage- Pet's Welcome & EV Charging

Annapolis
9.2 out of 10, Wonderful, (15)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
United States
Fr. Jamie C.
The price is AED 626
AED 1,342 total
includes taxes & fees
8 Dec - 9 Dec
Wright's Cottage- Pet's Welcome & EV Charging

Holly Hill Haven - Sleeps 10

Edgewater
10.0 out of 10, Exceptional, (3)
"Only thing is I would better stock the kitchen. Other than that NO COMPLAINTS! Great location, great clean and comfortable home to host thanksgiving "
United States
Brittany B.
The price is AED 558
AED 1,852 total
includes taxes & fees
9 Dec - 10 Dec
Holly Hill Haven - Sleeps 10

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

North Beach
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AED 480
AED 1,641 total
includes taxes & fees
16 Nov - 17 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater
9.8 out of 10, Exceptional, (24)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
United States
Mireia A.
The price is AED 698
AED 2,077 total
includes taxes & fees
19 Nov - 20 Nov
Edgewater/Mayo Gateaway w/ Hot Tub

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

Prince Frederick
10.0 out of 10, Exceptional, (8)
"This house was extremely clean and a comfortable choice for 4 older adults attending a family wedding in St Leonard. "
United States
Susan W.
The price is AED 588
AED 1,254 total
includes taxes & fees
25 Nov - 26 Nov
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

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

Cambridge
10.0 out of 10, Exceptional, (14)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Welcoming 3-bedroom townhome with AC in Waldorf

Waldorf
10.0 out of 10, Exceptional, (2)
"Location was perfect and the pool/ping pong table made it more enjoyable."
United States
pamela h.
The price is AED 592
AED 1,149 total
includes taxes & fees
22 Nov - 23 Nov
Welcoming 3-bedroom townhome with AC in Waldorf

Golden Anchor Retreat; Lux Living! - Sleeps 7

Edgewater
10.0 out of 10, Exceptional, (2)
"The property was very nice! Very spacious and very well put together. The communication with the owners is very good and helped a lot! The home was very clean. Nice garage for parking if you have more than 1 car traveling. We enjoyed our stay! "
United States
Karmen D.
The price is AED 731
AED 2,206 total
includes taxes & fees
18 Nov - 19 Nov
Golden Anchor Retreat; Lux Living! - Sleeps 7

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

Eastport
The price is AED 643
AED 1,231 total
includes taxes & fees
16 Nov - 17 Nov
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

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

Edgewater
10.0 out of 10, Exceptional, (1)
"Great place to stay for our race! Lovely neighbor!"
United States
Elizabeth S.
The price is AED 826
AED 1,311 total
includes taxes & fees
27 Nov - 28 Nov
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.

Prince Frederick
9.2 out of 10, Wonderful, (9)
"Got to go fishing, kayaking, and swimming in the pool. Had a great time, views are wonderful and it’s a peaceful environment. 10/10 would stay again."
United States
Timothy H.
The price is AED 1,058
AED 2,157 total
includes taxes & fees
16 Nov - 17 Nov
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.

Sunset Cottage - West River Access and Views!

2.0 star property
Shady Side
Sunset Cottage - West River Access and Views!
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