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Holiday Homes in Chesapeake Beach

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Featured Holiday Homes in Chesapeake Beach and around

Heated pool, sandy beach, pier, and playground set punch point apart!

10.0 out of 10, Exceptional, (10)
"Beautifully decorated, peaceful, well appointed home for our girls bday celebration. Highly recommend."
Heated pool, sandy beach, pier, and playground set punch point apart!

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"I cannot say enough about this property. Home was so spacious, views were wonderful, kitchen was very well stocked and just minutes to town. Highly recommend renting this home."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Rising Sun Bay View Cottage

10.0 out of 10, Exceptional, (1)
"What a great location for an awesome vacation rental. The three floors of the house is amazing and the views of the bay a huge added bonus. The house is well equipped, and you can tell that the owners stay there part time.The layout allows for socializing and fun on the middle level with a sitting areas and screened in porch while others can find some peace and quiet if needed on the upper or lower floorsThe private beach access is awesome and a true benefit. Will look to find this place again...
Rising Sun Bay View Cottage

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (46)
"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is €279
includes taxes & fees
27 Aug - 28 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (21)
"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."
Bay views with kayaks, bikes, fire pit, crabbing and more

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (21)
"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."
The price is €497
includes taxes & fees
19 Aug - 20 Aug
Edgewater/Mayo Gateaway w/ Hot Tub

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (131)
"Great house, host and location. Stayed with a larger group and plenty of room!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

10.0 out of 10, Exceptional, (39)
"Loved the location and the pristine condition of the house. "
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (66)
"Came for a wedding at Herrington on the Bay which was only a 5 minute drive away. Short walk to the beach and many restaurants in North Beach. Great for 4 people."
The Blue Crab Beach House - Free beach passes

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

9.8 out of 10, Exceptional, (18)
"We wanted to celebrate Easter with our two daughters who go to Loyola in Baltimore so we decided to stay in Annapolis area. We absolutely loved the house. The location and view was amazing- right on the Chesapeake bay! The house was clean and welcoming. There were so many nice little touches that made us feel welcomed. We had a great weekend celebrating Easter with our two daughters and son. The house was the perfect size for the 5 of us. "
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (121)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (40)
"Good location, clean house, easy check in and check out process."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (43)
"Our kids enjoyed the games in the crab house. It was great being able to use the kayaks and life vests."
The price is €417
includes taxes & fees
16 Sept - 17 Sept
Beautiful Waterfront Retreat in Cambridge!

WATERFRONT!!! The River's Roost on The Patuxent River

10.0 out of 10, Exceptional, (28)
"We had an amazing stay in this beautiful house! Inside was massive perfectly set up for our needs. Outside had stunning views and there is nothing better than being on the waters edge. The owners were easy to communicate with and they had everything ready in a timely manner for our check in. We didn’t get a chance to catch any crabs but we will definitely stay here again to try our hand at that."
WATERFRONT!!! The River's Roost on The Patuxent River

Unique and central in Eastport

Unique and central in Eastport

Eastport Cottage .5 mi from Downtown Annapolis

10.0 out of 10, Exceptional, (53)
"Terrific house and good location"
Eastport Cottage .5 mi from Downtown Annapolis

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

10.0 out of 10, Exceptional, (33)
"We had a wonderful stay on Tilghman Island at this beautiful property. The waterfront view from the house is stunning (as are the sunrises). We had fun using the kayak and walking over to Gina’s at the Bridge for lunch. It was a very relaxing stay!"
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

10.0 out of 10, Exceptional, (94)
"Great property and great time in Oyster Harbour!"
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

Brand-New Pool! Waterfront Bozman Village Home

Brand-New Pool! Waterfront Bozman Village Home
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