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Top Cities in Calvert County

Boardwalk along the Chesapeake Bay.
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Chesapeake Beach

Chesapeake Beach

Cottages in Calvert County

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!

Saint Michaels
9.6 out of 10, Exceptional, (122)
"The house and location was perfect for a girls weekend with my mom and 2 daughters! The 1/2 bathrooms in each bedroom were nice to have upstairs!"
United States
Kimberly L.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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, (57)
"This is a wonderful special place Tall Timbers, this house was lovely and perfect for our visit. The Lindley’s were very helpful and quickly responded to any communications. Wonderful place, if you have the chance to get away to this is a great place to stay."
United States
Kelly A.
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
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, (43)
"A beautiful stay on the Chesapeake."
United States
Craig C.
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
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, (14)
"Beautiful location, great views, beautiful sun rises, view of working watermen Dogwood Harbour. Owner met us at the property with a bottle of wine — very friendly. Tilghman Island is a quaint and beautiful gem."
United States
Frank P.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Fridge, microwave, oven, stovetop
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, (32)
"Cute cottage, close to Solomons Island, North Beach as well as many restaurants. Very clean."
United States
Susan B.
Cozy Cottage with access to and partially obstructed views of the bay.
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, (153)
"The place was great, the host was great,"
United States
Travis
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Exterior
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand

Point Lookout
10.0 out of 10, Exceptional, (125)
"We had a fantastic stay at the Hideaway in Hays Beach. We were coming up to see our 93yr old Grandmother who lives about 45 minutes away. Our families rented two homes in the area and were able to enjoy our time with three generations that aren’t able to see each other often. The home was exactly as shown, perfectly decorated and incredibly well stocked! We’d absolutely come back!"
United States
Seth H.
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand
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, (222)
"Very nice place, we will be visiting again!"
United States
Karen B.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Terrace/patio
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, (6)
"Sophia the host is super attentive and responsive"
United States
Mayela
$271 nightly
The price is $299
Nov 13 - Nov 14
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman
9.8 out of 10, Exceptional, (236)
"Enjoyed our stay. Very close to city center for restaurants, shopping, etc. "
United States
Corcoran 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, (14)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
United States
Dara M.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
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

Saint Michaels
9.8 out of 10, Exceptional, (191)
"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "
United States
Jen R.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Exterior
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

St Michaels
9.6 out of 10, Exceptional, (125)
"Beautiful house Great location. We really enjoyed our first visit to St. Michaels!"
United States
JIM S.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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)
"Everything was as advertised. Clean and tidy. Easy to find. Had everything we needed while visiting some state parks. Kids loved the beach and already asked to go back"
United States
Erik S.
Private Beach Front Getaway at The Sunshine Beach Cottage.
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)
"Nice "
United States
Henry
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Exterior
The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

Hillsmere
10.0 out of 10, Exceptional, (170)
"A lovely property in the perfect location! We will definitely rent again!"
United States
Donna R.
The Yellow Cottage on Harness Creek
Terrace/patio
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
United States
Sharon M.
$792 nightly
The price is $874
Dec 1 - Dec 2
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Exterior
Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!

Prince Frederick
10.0 out of 10, Exceptional, (42)
"Nice and quiet beautiful cottage. A+ communication and a gem. 10/10 will stay again."
United States
chris W.
$300 nightly
The price is $317
Nov 13 - Nov 14
Total with taxes and fees
Cottage Located on the Patuxent River!
Property grounds
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Epping Forest
9.8 out of 10, Exceptional, (30)
"We loved staying at the cottage. The atmosphere was incredibly peaceful and relaxing and the setting beautiful. Isaac was very helpful and thoughtful in responding to our questions and requests. "
United States
Alizah D.
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Fridge, microwave, oven, stovetop
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, (53)
"Just what we needed for an extended weekend getaway with family. The view of the water was do nice. House was very clean on arrival "
United States
Kim P.
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Wonderful country inn!"
Jennifer 4-night trip
Posted 8 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

Find out more about Calvert County

Calvert County Cottages information

Number of reviews
1,673
Accommodation
153 Cottages
Lowest Price
$299
Highest Price
$874

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