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Compare 57 Cottages in Chesapeake Beach with updated reviews, rates, and availability.

Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (211)
"As always our stay was amazing from kayaking, bird watching, sunsets. The cove is a special place."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Outdoor pool
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
10.0 out of 10, Exceptional, (38)
"My sister and I came back for the 2nd year in a row. We love your property. It’s got everything we needed. A nice pool and gazebo with a stunning view. "
The price is ￥19,132
￥40,407 total
includes taxes & fees
Sep 24 - Sep 25
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
The Yellow Cottage on Harness Creek
Smart TV, DVD player, books
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (148)
"This was just a super place- right in the water and beautiful… and surprisingly spacious for a cottage. I loved the kitchen farm sink and the sun coming in the morning off the bay. Will definitely love to stay again. The owner was so nice and thought of all the little details!! Thank you!!"
The Yellow Cottage on Harness Creek
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (107)
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Eastern Shore Waterside Cottage Near St. Michaels
Terrace/patio
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (18)
"We had a great stay at this house. We enjoyed using the kayak and paddleboard. (Access to the water is across this street.) We also enjoyed the pool and relaxing on the porch. It was about a 15 minute drive into St Michael’s, where we had excellent meals, went sailing, and enjoyed the cute shops and pretty houses. It was a really nice, relaxing weekend! "
Eastern Shore Waterside Cottage Near St. Michaels
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Property grounds
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (5)
"Our stay was amazing! Words cannot say enough! The view is magical. We enjoyed coffee on the porch to watch the sunrise and the crab/oyster boats going in and out. Maria, is a wonderful and very thoughtful host. At her recommendation, we went to the free wine tasting at the General Store at the end of the street. We met several local residents who could not be more kind and fun to talk with. We can't wait to come back and stay again."
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
Property grounds
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
10.0 out of 10, Exceptional, (1)
"If you want to get away from it all, this is the place to be. My wife and I celebrated our 20th wedding Anniversary. Calm and peaceful, nestled right by the Choptank River. The cottage itself was very comfortable. The air conditioner worked great. It was a pleasure staying there and we will probably return next year."
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
Cozy retreat in peaceful wooded setting. Pet friendly!
Exterior
Cozy retreat in peaceful wooded setting. Pet friendly!
2.0 star property
10.0 out of 10, Exceptional, (1)
"Private country setting with a short drive to civilization. Small studio style home easy to get around with open setting. Owners are super friendly and easy to communicate with"
Cozy retreat in peaceful wooded setting. Pet friendly!
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (199)
"What a lovely hideaway!!! The owners are extremely hospitable and the area is beautiful quaint and close to everything. Thank you for having us!!!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Property grounds
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (165)
"Great little cottage and plenty of space for our family of 3 to have an end-of-Summer getaway to one of our favorite towns. Prompt and easy communication with the owner, Tom, both before and during our stay. We loved the back porch and were blessed with some cooler temps and were able to enjoy sitting out there. FYI - Den has a door (third bedroom with pull out sofa). We have rented on Carpenter Street before, and the location cannot be beat as far as walkability to everything in town and along...
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (130)
"Had a wonderful time. This home was just perfect for us. Great location and charming. Would definitely stay here again"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Waterfront property with private boat ramp and new dock!
Outdoor dining
Waterfront property with private boat ramp and new dock!
9.2 out of 10, Wonderful, (5)
"Perfect size for a small family. Nice kitchen and furnishings, very cute. Nice quiet neighborhood setting."
Waterfront property with private boat ramp and new dock!
Cottage Located on the Patuxent River!
Sun loungers
Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (38)
"The property and the cottage are just beautiful [very quiet] and incredibly well appointed. The bed is super cozy. There is no kitchen but the coffee station was great to have. Note that the cottage shares the property with the main house. My husband and I enjoyed sitting by the river multiple times during our stay and we really appreciated our hosts’ hospitality and communication. Thank you for the beautiful respite!"
The price is ￥48,190
￥58,096 total
includes taxes & fees
Sep 24 - Sep 25
Cottage Located on the Patuxent River!
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Beach nearby
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
10.0 out of 10, Exceptional, (12)
"What a wonderful bungalow! Convenient location for Calvert Cliffs hiking, Cove Point lighthouse, PAX Naval Air Museum and Calvert Marine Museum. We really enjoyed the screened porch for relaxing and our meals. Special treat with the coffee bar. Kitchen was stocked with everything we needed. "
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Eastport Cozy Charmer
Fridge, microwave, oven, stovetop
Eastport Cozy Charmer
9.4 out of 10, Exceptional, (3)
"We really enjoyed our stay. We felt very comfortable there, and it worked well for us. Especially liked that there was space to park the boat on the street next to the house."
Eastport Cozy Charmer
Pet-friendly Annapolis Home: Walk to Beach!
Interior
Pet-friendly Annapolis Home: Walk to Beach!
3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
Enchanting West River Retreat
Outdoor dining
Enchanting West River Retreat
10.0 out of 10, Exceptional, (5)
"The views are spectacular and the boat dock is lovely..the hospitality was amazing too can’t wait to come back and visit "
Enchanting West River Retreat
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (114)
"We love escaping to St Michaels for a change of scenery. These historic properties are great places to disconnect from our normal fast paced lifestyle. We always enjoy that our dogs are able to enjoy our stay. It’s a vacation for them as well. The town is very dog friendly in general. The properties are historic and have their quirks. For us, this adds to the experience and charm of St Michaels. The centralized location is key. "
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Updated North Beach Cottage: Pet Friendly!
Fridge, microwave, stovetop, dishwasher
Updated North Beach Cottage: Pet Friendly!
9.8 out of 10, Exceptional, (10)
"We had a great time. Nice place. Within walking distance to small deli/ market. Just wished we wouldn't have had to pay to go to the beach."
Updated North Beach Cottage: Pet Friendly!
The Middle Point Cabin in Saint Michaels
Fridge, microwave, oven, stovetop
The Middle Point Cabin in Saint Michaels
9.8 out of 10, Exceptional, (48)
"nice property. secluded. clean and comfortable. owners very very responsive. "
The Middle Point Cabin in Saint Michaels
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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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Other property types in Chesapeake Beach

Mid-Century Modern and Marvelous on the Bay
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (65)
"Everything I expected and more. Quite beautiful."
Mid-Century Modern and Marvelous on the Bay
Family Beach House: Spacious Deck, Grill & Views
Pool
Family Beach House: Spacious Deck, Grill & Views
9.4 out of 10, Exceptional, (3)
"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."
The price is ￥20,714
￥65,141 total
includes taxes & fees
Sep 24 - Sep 25
Family Beach House: Spacious Deck, Grill & Views
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (83)
"The house was clean and comfortable. Walking distance to a local restaurant. Screened porch was great for watching the sunrise in the morning and the boats coming in and out of harbor "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
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.

Frequently asked questions

Why book your cottage in Chesapeake Beach with Expedia?
Expedia has some wonderful cottages in Chesapeake Beach, so start planning for a memorable vacay close to nature. If you need to stick to a budget, select how much you want to spend and the star rating of your property. Or, make the most of our filters to search for cottages with a pool or a kitchen. We’ll help you find a suitable place whatever your trip looks like.
How can I find cheap cottages in Chesapeake Beach?
With Expedia’s helpful filter tool, getting your hands on cheap cottages in Chesapeake Beach is a snap. To discover stays that are friendly on the wallet, narrow your search results by amenities, budget and star rating.
What is there to do in Chesapeake Beach near my cottage?
The best travel accessory is a well-planned itinerary. Breezy Point Beach is an excellent place to start your adventures in Chesapeake Beach.