Cottages in Calvert County

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Top Cities in Calvert County

Our top choices for Calvert County cottages

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

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Downtown St. Michaels
9.8 out of 10, Exceptional, (198 reviews)
"Great property! The house has everything you'd need and the location couldnt be better. "
United States
Joe C.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

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

"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Tilghman Island
10.0 out of 10, Exceptional, (15 reviews)
"Amazing property well presented with fantastic views in all directions"
United Kingdom
David G.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Point Lookout
10.0 out of 10, Exceptional, (126 reviews)
"My family loved the fishing and crabbing. There were so many tools and toys available. Would love to make this a birthday and family tradition! "
United States
Hannah A.
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier
Cambridge
10.0 out of 10, Exceptional, (265 reviews)
Family and Pet-Friendly, Waterfront with Pier

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Stevensville
10.0 out of 10, Exceptional, (62 reviews)
"great stay ! all needs where met . "
United States
randall j.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Downtown St. Michaels
9.6 out of 10, Exceptional, (126 reviews)
"Ideal location to shops and attractions. Host very easy to reach. "
United States
Don N.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

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

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Lusby
10.0 out of 10, Exceptional, (55 reviews)
"Incredible property and stay."
United States
Hunter B.
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

2 Bedroom Cozy Beach Cottage with Water Access

2 Bedroom Cozy Beach Cottage with Water Access
Piney Point
9.6 out of 10, Exceptional, (22 reviews)
"Great place to stay"
United States
Sean H.
2 Bedroom Cozy Beach Cottage with Water Access

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (240 reviews)
"A cozy cottage, definitely met our needs. Beautiful view!"
United States
Cynthia Louise C.
Relaxing Waterfront Cottage Near St Michaels, Maryland

Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (46 reviews)
"Wonderful views, clean home and quaint ! We highly recommend!"
United States
Tim R.
Cozy Virginia Potomac Riverfront Cottage

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

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Edgewater
10.0 out of 10, Exceptional, (225 reviews)
"Awesome location and very nice, we had a great stay! "
United States
Megan B.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (42 reviews)
"House was very nice and tidy and exactly as described. The host had a small binder full of helpful info including local restaurants and attractions. There was so much to do and everything was close bye. "
United States
Mindy V.
The price is AED 459
AED 1,028 total
includes taxes & fees
8 Apr - 9 Apr
Soul Oasis - home on the Chesapeake Bay

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.4 out of 10, Exceptional, (12 reviews)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
The price is AED 731
AED 1,488 total
includes taxes & fees
26 Mar - 27 Mar
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cottage downtown on a quiet street

Cottage downtown on a quiet street
Downtown St. Michaels
9.8 out of 10, Exceptional, (59 reviews)
"It's a very nice place and the location is great. Its not a professionally managed house which is fine, but we didn't know that going in. Everything is clean, but not professionally clean i.e. the sheets are clean but the mattress pad was not. I would stay there again."
United States
Casey G.
Cottage downtown on a quiet street

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (17 reviews)
"This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!"
United States
Linda Q.
The price is AED 1,127
AED 2,068 total
includes taxes & fees
26 Mar - 27 Mar
Secluded Cozy Cottage in Historic Downtown

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

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Downtown St. Michaels
9.4 out of 10, Exceptional, (130 reviews)
"Beautiful little cottage! Location is perfect."
United States
John B.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC

Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC
Royal Oak
Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC

Lovely 2-bedroom waterfront cottage in charming Wittman

Lovely 2-bedroom waterfront cottage in charming Wittman
Wittman
10.0 out of 10, Exceptional, (1 review)
"I recently stayed at this lovely VRBO, and it exceeded my expectations in every way. From the moment I walked in, the home felt incredibly cozy and welcoming. Everything was spotless—truly one of the cleanest vacation rentals I’ve stayed in—which immediately set the tone for a relaxing visit.The space itself is bright and airy, with plenty of natural light that makes the home feel open and refreshing throughout the day. It’s thoughtfully furnished and had everything I needed for a comfortable...
United States
Mario V.
Lovely 2-bedroom waterfront cottage in charming Wittman

Your Annapolis Waterfront retreat - ready for a winter getaway!

Your Annapolis Waterfront retreat - ready for a winter getaway!
West Annapolis
10.0 out of 10, Exceptional, (89 reviews)
"Great location and a beautiful place, thanks Jim. "
United States
Michael M.
Your Annapolis Waterfront retreat - ready for a winter getaway!

Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset

Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
Tall Timbers
9.8 out of 10, Exceptional, (60 reviews)
"Lovely house with great hosts. Would stay there again. "
United States
Chad C.
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
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