A beach with seagulls, a rocky shoreline, and houses in the background.

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

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

Our top choices for Calvert County cottages

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
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, (10 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 CA $239
CA $406 total
includes taxes & fees
Jul 20 - Jul 21
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek
Hillsmere
10.0 out of 10, Exceptional, (178 reviews)
"We had a great time and really enjoyed the cottage."
United States
Craig M.
The Yellow Cottage on Harness Creek
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (55 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
The price is CA $212
CA $445 total
includes taxes & fees
Jul 22 - Jul 23
Soul Oasis - home on the Chesapeake Bay
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, (230 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
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, (83 reviews)
"Amazing getaway! Quiet, peaceful, beautiful views. "
United States
Sarah H.
Private Beach Front Getaway at The Sunshine Beach Cottage.
Exterior

Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier
Cambridge
10.0 out of 10, Exceptional, (271 reviews)
"The hosts were very welcoming, helpful, good communication throughout the reservation process and stay."
United States
Ann R.
Family and Pet-Friendly, Waterfront with Pier
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, (22 reviews)
"The views are an amazing. The cottage is well appointed. The hosts were responsive. It was an excellent trip"
United States
Paul H.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Terrace/patio

Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island
Fishing Creek
10.0 out of 10, Exceptional, (85 reviews)
"It is a beautiful place to visit!"
United States
Yoon G.
Waterfront Cottage in Beautiful Hoopers Island
Smart TV

Beautiful Waterfront 2-bedroom cottage in tranquil Piney Point with WiFi, AC

Beautiful Waterfront 2-bedroom cottage in tranquil Piney Point with WiFi, AC
Piney Point
10.0 out of 10, Exceptional, (7 reviews)
"We had a great time! The cottage was perfect for our needs and clean. We loved spending time in the water on the paddle boat. "
United States
Samantha D.
Beautiful Waterfront 2-bedroom cottage in tranquil Piney Point with WiFi, AC
Outdoor spa tub

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Deale
9.8 out of 10, Exceptional, (87 reviews)
"Love, love, love this home! I brought my pup and it was just a perfect mini vacation. Shawn is incredibly kind, communicative, and just a lovely woman all around. The kitchen was fully stocked with everything I needed to cook meals. Beds were super comfy! Cannot recommend this home enough. :)"
United States
Stephanie V.
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Smart TV, fireplace, books

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

Cozy Cottage with access to and partially obstructed views of the bay.
Port Republic
9.2 out of 10, Wonderful, (33 reviews)
"Lovely quiet area, very comfortable beds! Hosts very friendly and helpful. Would highly recommend!"
United States
Linda C.
Cozy Cottage with access to and partially obstructed views of the bay.
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!
Exterior

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
Annapolis
9.8 out of 10, Exceptional, (42 reviews)
"Excellent location for a relaxing weekend with our dogs and midshipman! "
United States
Celine D.
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
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.
Exterior

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, (129 reviews)
"We had a great time. The house was so charming and the location was perfect. Can't wait to go back!"
United States
Anonymous traveller
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (250 reviews)
"Very clean and enjoyable stay! We loved the quiet neighborhood, relaxing atmosphere, and convenience to a variety of things to do. "
United States
Aaron &amp; Kayla C.
Relaxing Waterfront Cottage Near St Michaels, Maryland
Outdoor dining

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

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cambridge
10.0 out of 10, Exceptional, (16 reviews)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Property grounds

Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.

Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.
Maddox
10.0 out of 10, Exceptional, (21 reviews)
"Absolutely beautiful cottage!!!! Thank you so much for having such a beautiful home for my family to enjoy for the weekend! We will definitely remember the breathtaking view and quietness of this cottage. "
United States
Lindsey M.
Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Beautiful hotel. Very clean and amazing staff."
Lena 1-night trip
Posted 2 hours ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Calvert County

Calvert County Cottages information

Number of reviews
1,331
Accommodation
159 Cottages
Lowest Price
CA $406
Highest Price
CA $445

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