Cottages in Calvert County

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Top Cities in Calvert County

Aerial view of Chesapeake Beach marina with luxury sail boats, beach house apartments, fishing boats near the water park popular vacation spot for Washington residents in Calvery county Maryland
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

Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (46 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
The price is AED 529
AED 1,117 total
includes taxes & fees
26 May - 27 May
Soul Oasis - home on the Chesapeake Bay
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (243 reviews)
"A cozy cottage, definitely met our needs. Beautiful view!"
United States
Cynthia Louise C.
Relaxing Waterfront Cottage Near St Michaels, Maryland
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, (126 reviews)
"Perfect place for a quiet getaway at the beach!"
United States
Cheryl S.
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
Exterior

"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, (17 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
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
9.0 out of 10, Wonderful, (8 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 562
AED 977 total
includes taxes & fees
11 May - 12 May
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Property grounds

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, (80 reviews)
"Amazing getaway! Quiet, peaceful, beautiful views. "
United States
Sarah H.
Private Beach Front Getaway at The Sunshine Beach Cottage.
Exterior

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)
"Our dog was so comfortable and welcome at this rental!"
United States
Kathie F.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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, (155 reviews)
"Good place for a couple for a relaxing weekend on the waterfront"
United States
Elizabeth B.
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, (202 reviews)
"Perfect house close to St Michael’s attractions"
United States
Carolyn E.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Property grounds

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, (127 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!
Exterior

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
West River
9.8 out of 10, Exceptional, (45 reviews)
"This was such a beautiful property right on the water! It was everything I wanted for a quiet weekend away. The host was quick to respond and full of great recommendations. I am definitely planning on staying here again and will recommend it to anyone else 10/10"
United States
Meghan G.
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
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, (50 reviews)
"We love this place!"
United States
Joan K.
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
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, (13 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
TV, books

Chesapeake Bay Vacation Rental w/ Boat Dock!

Chesapeake Bay Vacation Rental w/ Boat Dock!
Newburg
8.0 out of 10, Very Good, (15 reviews)
"Outdoor space is amazing. Sitting out by the fire was great"
United States
Ryan E.
Chesapeake Bay Vacation Rental w/ Boat Dock!
Exterior

Beachfront Home Minutes to Downtown Annapolis Dogs OK

Beachfront Home Minutes to Downtown Annapolis Dogs OK
Annapolis
9.8 out of 10, Exceptional, (40 reviews)
"Excellent location for a relaxing weekend with our dogs and midshipman! "
United States
Celine D.
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Exterior detail

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
North Beach
9.6 out of 10, Exceptional, (4 reviews)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Exterior

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Fishing Creek
10.0 out of 10, Exceptional, (51 reviews)
"Nice "
United States
Henry
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Outdoor dining

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
Outdoor dining

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Deale
9.8 out of 10, Exceptional, (84 reviews)
"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."
United States
Paul M.
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
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

Days Inn by Wyndham Lanham Washington DC

Days Inn by Wyndham Lanham Washington DC

10/10 Excellent
"Great stay"
Michael 1-night trip
Posted 4 hours ago
Days Inn by Wyndham Lanham Washington DC