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Search Cottages in Chesapeake Beach

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Compare 58 Cottages in Chesapeake Beach with updated reviews, rates, and availability.

Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (215)
"Manager alway accessible, helpful and friendly. Neighborhood very quiet. The view can’t be beat. Hope to be able to enjoy it for years to come. "
Relaxing Waterfront Cottage Near St Michaels, Maryland
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (111)
"Perfect stay in a historic home in the heart of town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (5)
"We thoroughly enjoyed our long weekend stay. We spent great time together in the cozy and spacious living room, as well as enjoying the nice waterfront outdoor areas. The house is unique, well equipped, very clean, and with great attention to details in every room. Host was very proactive and responsive in the communication. Canoes and bikes are available, what we enjoyed. Views from the house were wonderful, including a beautiful sunrise. It was a very relaxing family weekend and we can’t wait...
The price is SAR 1,686
SAR 3,560 total
includes taxes & fees
12 Nov 2024 - 13 Nov 2024
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (202)
"This was a lovely home. I especially appreciated how clean and well-stocked it was. Liz and Tom were very responsive and accommodating! This truly added to a wonderful reunion weekend with friends and family. Thank you!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (114)
"Waters edge is just a few steps away to sit and watch boats come in and out. So cute and the most amazing artifacts decorating the place made it even more captivating. Short walk to coffee, food and shopping local. The owner was responsive and kind as well as super easy to work with. Will definitely return."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (19)
"Wonderful property in a beautiful setting. We had a lovely weekend with family. Would highly recommend the property!"
Eastern Shore Waterside Cottage Near St. Michaels
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (132)
"Fine stay pretty quiet off season"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
9.8 out of 10, Exceptional, (33)
"A beautiful stay on the Chesapeake."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (7)
"“Point of View” waterfront cottage did not disappoint. In fact, it was beyond expectations. Maria’s (the host) personal touches made the cottage feel like home. We used “Point of View” as overflow for a family reunion we were having. It is perfectly situated for easy walking to anything you need or want to do on Tilghman Island. The views from the cottage are amazing. Being on the entrance to Dogwood Harbor provides you with a real time experience of what a waterman’s life is truly all...
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Waterfront property with private boat ramp and new dock!
9.6 out of 10, Exceptional, (8)
"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!
North Beach Cottage - Walk to Chesapeake Bay
10.0 out of 10, Exceptional, (27)
"This little farmhouse is great. Updated and very clean with an unbelievable location just a short walk to the beach. "
North Beach Cottage - Walk to Chesapeake Bay
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
Pet-friendly Annapolis Home: Walk to Beach!
3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (154)
"Great cottage along a quiet road in a private setting. This is just what my family was looking for to escape the busy weekend in Annapolis. Will not hesitate to schedule future stays at this home."
The Yellow Cottage on Harness Creek
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (168)
"We went to St. Michael’s for a wedding. The cottage was great. Very charming. The location was perfect. We could walk everywhere. We had great communication with the host. He was very accommodating. We will stay there again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
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
9.8 out of 10, Exceptional, (48)
"nice property. secluded. clean and comfortable. owners very very responsive. "
The Middle Point Cabin in Saint Michaels
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
10.0 out of 10, Exceptional, (39)
"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 SAR 526
SAR 1,095 total
includes taxes & fees
4 Nov 2024 - 5 Nov 2024
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Cozy Cottage with access to and partially obstructed views of the bay.
9.4 out of 10, Exceptional, (13)
"Away from the hustle and bustle of any city but close enough to get anything you need. Our stay was very relaxing and Hyrum and Lisa were the best hosts we have had so far... Will definitely look for them again if we are in the area again..."
Cozy Cottage with access to and partially obstructed views of the bay.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (2)
"This was an amazing property. Very clean and very cute and cozy. Beautiful property. The owners were fantastic. Very responsive and caring. Loved it! Would definitely return."
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
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
10.0 out of 10, Exceptional, (68)
"The ratings were Exceptional, so I was skeptical. However, it was beyond exceptional. The most well equipped rental we have seen. Great location. Well stocked. Excellent communication with the host. Couldn’t have asked for anything more. Definitely recommend, and will stay here again when in the area. We had a great time."
Mid-Century Modern and Marvelous on the Bay
Family Beach House: Spacious Deck, Grill & Views
9.6 out of 10, Exceptional, (4)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is SAR 638
SAR 1,824 total
includes taxes & fees
6 Nov 2024 - 7 Nov 2024
Family Beach House: Spacious Deck, Grill & Views
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW 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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