Cottages in Calvert County

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Top Cities in Calvert County

A harbor with boats docked, a pier, and a row of houses along the water.
CottagesCottages

Chesapeake Beach

Chesapeake Beach
House on the boardwalk and the shore of the Chesapeake Bay, in North Beach, Maryland
CottagesCottages

North Beach

North Beach

Our top choices for Calvert County cottages

Property grounds

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.2 out of 10, Wonderful, (9 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is AED 624
AED 1,055 total
includes taxes & fees
8 Jul - 9 Jul
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (51 reviews)
"Everything was great! Just read the book about the property and amenities…some crucial details about heat and hiking around the neighborhood. Definitely would stay again!"
United States
Chris G.
The price is AED 569
AED 1,176 total
includes taxes & fees
7 Jul - 8 Jul
Soul Oasis - home on the Chesapeake Bay
Exterior

The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek
Hillsmere
10.0 out of 10, Exceptional, (174 reviews)
"We had a great time and really enjoyed the cottage."
United States
Craig M.
The Yellow Cottage on Harness Creek
Terrace/patio

Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger

Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Point Lookout
10.0 out of 10, Exceptional, (20 reviews)
"We loved our stay and are looking forward to going back! I have already recommended it to friends that are looking for a quiet retreat in a great location."
United States
Melissa K.
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Exterior

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Tilghman Island
10.0 out of 10, Exceptional, (15 reviews)
"Everything about the place was perfect for a getaway loved the place everything was handy and setup perfectly to relax and enjoy the scenery "
United States
David M.
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Exterior

Updated North Beach Cottage: Pet Friendly!

Updated North Beach Cottage: Pet Friendly!
North Beach
9.6 out of 10, Exceptional, (27 reviews)
"Cozy cottage, beds were comfy and it was great to bring our dog. "
United States
Chloe W.
Updated North Beach Cottage: Pet Friendly!
Terrace/patio

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

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Newburg
9.8 out of 10, Exceptional, (161 reviews)
"Lovely place and location!"
United States
Christa W.
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Exterior

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, (203 reviews)
"We had a wonderful time and really enjoyed the back screened in porch which is where we spent a lot of time with our two little dogs."
United States
LeaAnne T.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Property grounds

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
Point Lookout
10.0 out of 10, Exceptional, (132 reviews)
"Wonderful three nights! This is our second time staying at this little slice of heaven! Ten steps to the bays edge. We found lots of sea glass and enjoyed the quiet. "
United States
Sandy R.
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
Outdoor dining

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Saint Leonard
10.0 out of 10, Exceptional, (20 reviews)
"The house was very nice and had great amenities supplied by the owners. "
United States
Kenly
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Exterior

Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Navy Sports visitors and the Annapolis Blues games!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Navy Sports visitors and the Annapolis Blues games!
West Annapolis
10.0 out of 10, Exceptional, (92 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Navy Sports visitors and the Annapolis Blues games!
Exterior

Beachfront Home Minutes to Downtown Annapolis Dogs OK

Beachfront Home Minutes to Downtown Annapolis Dogs OK
Annapolis
9.8 out of 10, Exceptional, (41 reviews)
"Excellent location for a relaxing weekend with our dogs and midshipman! "
United States
Celine D.
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Outdoor dining

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
Bozman
Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
Exterior

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, (69 reviews)
"Our stay was wonderful. The house is very comfortable and immaculate. Everything worked beautifully. The three season screened-in porch and backyard were inspiring with ideas for our own houses. Mark and Karen could easily have a design and landscaping design business; they are also phenomenal hosts! The house is an absolute pleasure! We hope to stay many more times. I highly recommend.. "
United States
Marguerite W.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Terrace/patio

Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island
Fishing Creek
10.0 out of 10, Exceptional, (84 reviews)
"Host was great communicating, place was perfect for a quiet New Year's getaway. Would love to come back in the summer. Thanks for the hospitality."
United States
Curtis C.
Waterfront Cottage in Beautiful Hoopers Island
Exterior

Private Beach Front Getaway at The Sunshine Beach Cottage.

Private Beach Front Getaway at The Sunshine Beach Cottage.
Point Lookout
9.8 out of 10, Exceptional, (82 reviews)
"Amazing getaway! Quiet, peaceful, beautiful views. "
United States
Sarah H.
Private Beach Front Getaway at The Sunshine Beach Cottage.
Exterior

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, (62 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
Property grounds

Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (47 reviews)
"Wonderful views, clean home and quaint ! We highly recommend!"
United States
Tim R.
Cozy Virginia Potomac Riverfront Cottage
Property grounds

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Owings
10.0 out of 10, Exceptional, (52 reviews)
"We love this place!"
United States
Joan K.
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Exterior

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.6 out of 10, Exceptional, (16 reviews)
"Hosts were very helpful. The cottage is adorable and well maintained. "
United States
William L.
The price is AED 780
AED 1,559 total
includes taxes & fees
15 Jul - 16 Jul
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great location. Walking distance to restaurants and museums."
Lolly 3-night trip
Posted 2 hours ago
Graduate by Hilton Annapolis