Holiday Rentals in Calvert County

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Top Cities in Calvert County

Holiday RentalsHoliday Rentals

Chesapeake Beach

Chesapeake Beach

Featured Holiday Rentals in Calvert County

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Dining

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (179)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds

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

9.6 out of 10, Exceptional, (120)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Fridge, microwave, oven, stovetop

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

10.0 out of 10, Exceptional, (13)
"The host was amazing. The property was as described and was perfect for our group. "
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Floating 2 bed 2 bath condo stunning views of the bay
Marina

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
6.8 out of 10, (5)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
Floating 2 bed 2 bath condo stunning views of the bay
Waterfront Getaway, Dock Your Boat & Play!
Outdoor dining

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is €283
includes taxes & fees
21 Oct - 22 Oct
Waterfront Getaway, Dock Your Boat & Play!
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Terrace/patio

Tiny, Funky, and Full of Love - Welcome to the Love Shack

9.8 out of 10, Exceptional, (9)
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (47)
"Our large family of adults and two one-year-olds and a dog had a perfect week. The hosts were kind and responsive, and the home was spacious with lots of room for privacy and being all together. Looking forward to going again!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Charming townhome with AC and WiFi in delightful Annapolis
Interior

Charming townhome with AC and WiFi in delightful Annapolis

4.0 out of 10, (1)
"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "
The price is €91
includes taxes & fees
4 Nov - 5 Nov
Charming townhome with AC and WiFi in delightful Annapolis
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Fridge, microwave, oven, stovetop

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.4 out of 10, Exceptional, (16)
"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"
The price is €1,083
includes taxes & fees
3 Nov - 4 Nov
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds

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

9.8 out of 10, Exceptional, (151)
"The place was great, the host was great,"
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (259)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier
Quaint 3/2.5 home in Fort Dupont
Private kitchen

Quaint 3/2.5 home in Fort Dupont

7.4 out of 10, Good, (25)
"The house was clean and close to where I needed to go. We will be back. "
The price is €237
includes taxes & fees
6 Oct - 7 Oct
Quaint 3/2.5 home in Fort Dupont
Message me for additional Discount |FREE Parking
Cookware/dishes/utensils, paper towels, dining tables

Message me for additional Discount |FREE Parking

10.0 out of 10, Exceptional, (2)
"Awesome property and host."
The price is €439
includes taxes & fees
30 Oct - 31 Oct
Message me for additional Discount |FREE Parking
Riverfront Retreat 7mil from MD Renaissance Fest!
Exterior

Riverfront Retreat 7mil from MD Renaissance Fest!

9.2 out of 10, Wonderful, (17)
"Wonderful spot for large group. House was massive. Comfortably slept 17 of us. The views of the canals were great and close to Annapolis. Would definitely come back. "
Riverfront Retreat 7mil from MD Renaissance Fest!
Hidden Gem@Capitol Hill, 4BDR,2.5BA , 2 Blocks to Metro - DowntownDC, DCA, IAD
Fridge, microwave, oven, stovetop

Hidden Gem@Capitol Hill, 4BDR,2.5BA , 2 Blocks to Metro - DowntownDC, DCA, IAD

9.8 out of 10, Exceptional, (35)
"Accommodations as depicted, close to the Metro, nice neighborhood "
The price is €558
includes taxes & fees
14 Oct - 15 Oct
Hidden Gem@Capitol Hill, 4BDR,2.5BA , 2 Blocks to Metro - DowntownDC, DCA, IAD
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

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

9.8 out of 10, Exceptional, (187)
"Excellent accommodations. Comfortable, good location.One way you could improve is to furnish wash cloths and hand towels. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Beautiful Three Bedroom in SE DC
Fridge, microwave, oven, stovetop

Beautiful Three Bedroom in SE DC

9.6 out of 10, Exceptional, (7)
"The property was very cleab. Everything that you wiuld need was already there. Very comfortable. Would highly recommend. "
Beautiful Three Bedroom in SE DC
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Outdoor pool, a heated pool

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Top Location | Free Breakfast + Fitness Center
Exterior

Top Location | Free Breakfast + Fitness Center

2.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice!"
Top Location | Free Breakfast + Fitness Center
Presidential Style Retreat up to 22 guests!! Pet Friendly and Free Parking!!
Fridge, microwave, oven, stovetop

Presidential Style Retreat up to 22 guests!! Pet Friendly and Free Parking!!

2.0 star property
10.0 out of 10, Exceptional, (2)
"The check process was super easy. The house was very very spacious for 9 people. I will recommend thos property lookong to stay in DC with a large party."
Presidential Style Retreat up to 22 guests!! Pet Friendly and Free Parking!!
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

Harborside Hotel

Harborside Hotel

10/10 Excellent
"Great location. Room was very clean! Free shuttle to MGM and the outlets. Staff very friendly."
Nicole 1-night trip
Posted 4 hours ago
Harborside Hotel

Find out more about Calvert County

Find out more about Calvert County

Holiday Homes in Calvert County

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