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Boardwalk along the Chesapeake Bay.
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Chesapeake Beach

Cottages in Calvert County

Relaxing Waterfront Cottage Near St Michaels, Maryland
Situated on a serene grassy area, this charming home features a two-story design with a prominent chimney and a cozy porch with white railings.

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (224)
"We had a lovely stay here.Place was VERY clean.Visited St. Michael’s and relaxed on the porch & pier.It met our expectations."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Traditional home with a gabled roof and central chimney, set amidst a peaceful grassy lawn and trees.

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (121)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Terrace/patio

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (140)
"We stayed here for the weekend while attending a car show at the raceway close by. Very private and welcoming. Great place to relax and unwind after a long day. "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
The Yellow Cottage on Harness Creek
Traditional house with a front porch surrounded by lush gardens and flowering plants.

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (162)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
Waterfront property with private boat ramp and new dock!
Sit and enjoy the view from this shaded patio with a round table and two chairs.

Waterfront property with private boat ramp and new dock!

9.4 out of 10, Exceptional, (13)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Overlooking the water, this property offers a balcony with a view of the surrounding trees and a distant bridge.

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (11)
"The home was so well appointed and walking distance to stores, restaurants, quaint museums and beautiful nature. The host was so friendly and helpful with quick responses. We had high winds and lots of rain, but stayed cozy and warm. What a friendly Island of people!!"
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Private Beach Front Getaway at The Sunshine Beach Cottage.
Situated on a property, this charming single-story building features a covered porch with a table and chairs for outdoor dining or relaxation.

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (71)
"If you want to relax by the water and getaway from the hustle and bustle, this is the place. The cottage is updated and cozy with amazing views. Just step off the patio onto the sand. Cottage was stocked with essentials and extra goodies to make it feel like home."
Private Beach Front Getaway at The Sunshine Beach Cottage.
Waterfront Cottage in Beautiful Hoopers Island
Relax in Adirondack chairs on the deck overlooking a serene landscape with a tranquil body of water.

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (75)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Enjoy a peaceful outdoor space with a table, chairs, and umbrella, surrounded by a tree and scenic views.

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (7)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Enjoy a patio surrounded by lush trees and a well-manicured lawn.

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (184)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Cozy Cottage with access to and partially obstructed views of the bay.
Relax in Adirondack chairs on the beach, overlooking the calm sea.

Cozy Cottage with access to and partially obstructed views of the bay.

9.0 out of 10, Wonderful, (26)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.
Quick walk to the beach! Fire pit, Corn hole, Games & More!
Relax on the spacious outdoor deck with a comfortable sofa and bench, surrounded by lush greenery and a wooden railing.

Quick walk to the beach! Fire pit, Corn hole, Games & More!

10.0 out of 10, Exceptional, (1)
"We loved EVERYTHING about this place. Right next to the beach, great restaurants and shops. Could not have been better service. "
Quick walk to the beach! Fire pit, Corn hole, Games & More!
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Enjoy cooking in this well-equipped kitchen with a stainless steel stove, oven, and microwave, along with a large sink and gold faucet.

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

10.0 out of 10, Exceptional, (49)
"It’s a wonderful house with everything you need. The views are amazing - perfection! "
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Guests can enjoy a tranquil atmosphere and scenic views from the covered porch.

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (117)
"It was a great stay!"
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Relax on the front porch with a bench and two chairs, surrounded by a serene garden and a wooded area.

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (50)
"Beautiful home with LOTS of attention to detail. The backyard was a beautiful oasis and we LOVED the “swing bed” on the screened-in porch. Mark and Karen add lots of fine touches to make your stay special. Plenty of room for two, cozy for four, and comfortable for four legged friends with the fenced in back yard. Quiet and private with a short 10 minute drive to town. Can’t wait to return!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Family and Pet-Friendly, Waterfront with Pier
Escape to a serene forest retreat with a cozy cabin-style lodge featuring a sheltered front porch and breathtaking natural views.

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (253)
"What a wonderful area on the water. The proprietors were such friendly and accommodating people. The apartment was clean and well stocked. They had a wide range of activities on the property. It was wonderful being able to sit near the water and enjoy my friend’s company. I highly recommend this welcoming place. "
Family and Pet-Friendly, Waterfront with Pier
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Enjoy al fresco dining and social gatherings on this shaded deck with a grill and comfortable seating.

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (213)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Soul Oasis - home on the Chesapeake Bay
Cozy cabin nestled in a forest setting, featuring a front entrance with a door and stairs.

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (31)
"The A-frame cottage was clean and comfortable. I was accompanied by my son and two grandchildren (ages 12 and 14), and we really loved it. We went fishing in bay at the beach area below the cottage, and also did a lot of fossil hunting along the cliffs, which are breathtaking. Our host Teresa was extremely helpful and welcoming. We will definitely be going back!"
$296 nightly
The price is $314
Aug 18 - Aug 19
Total includes taxes and fees
Soul Oasis - home on the Chesapeake Bay
Secluded Cozy Cottage in Historic Downtown
Stroll along the pathway to an entrance surrounded by lush greenery and a curved brick wall.

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (13)
"We had a very lovely stay . This is an excellent location . "
$669 nightly
The price is $763
Aug 13 - Aug 14
Total includes taxes and fees
Secluded Cozy Cottage in Historic Downtown
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Situated in a residential area, this house features a charming front porch and a covered entryway, surrounded by a well-manicured lawn and beautiful gardens.

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

10.0 out of 10, Exceptional, (48)
"The house was exactly how the pictures showed !Cute and cozy ,and clean ! Im a country girl and felt at home sitting on the porch,enjoying the breeze. The sound of the ocean was a bonus!! Quiet and peaceful. I enjoyed the beautiful sunrises and morning walk on the dock. Overall i enjoyed my stay appreciate the hospitality of the host and would booked again !! "
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, 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 Calvert County Hotel Reviews

Hyatt Place National Harbor

Hyatt Place National Harbor

10/10 Excellent
"Great staff and location and they always make my stays great "
Scott 1-night trip
Posted 1 day ago
Hyatt Place National Harbor