Calvert County Holiday Rentals

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Top Holiday Rentals Destinations in Calvert County

Relax on the deck with ocean views, featuring a table and chairs.

"The views are fantastic. Very quiet neighborhood. "

"The place was inviting and beautiful. Will definitely stay there again."

Enjoy a marina view from the bay window, featuring a glass-top table and chair.

"The location is great with amazing views of the docks and very walkable to the boardwalk, restaurants, and the Solomon museum. Apartment was cozy with great communication from the hosts. Would recommend to anyone! "

includes taxes & fees

11 Aug - 12 Aug

Enjoy meals al fresco on this deck surrounded by lush greenery.

"Had a great time fishing from the dock while we got out of the city for a weekend."

Enjoy cooking in this well-equipped kitchen with a large island, ample counter space, and plenty of storage.

"Nice, comfy, thoughtful and well done handbook, great location, super clean and even ice cubes were made and ready’"

Relax on the lakeside deck with two comfortable lounge chairs and a shaded area.

"We stayed here for the weekend while attending a car show at the raceway close by. Very private and welcoming. Great place to relax and unwind after a long day. "

Guests can access the marina from this dock, where several boats are moored.

"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "

Enjoy meals in this kitchen with a dining table, sink island, and window view.

"Absolutely perfect location to get away for the weekend. It was so peaceful and we saw osprey and deer in the back yard. You have access to a dock which is fantastic at night to see the stars. The house has everything you could need. They have 2 kayaks we intended to use but ran out of time. The best part was sitting outside at night with a fire. Would absolutely stay again! "

Relax in a serene outdoor space with a comfortable seating area and picturesque views of the surrounding forest.

"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"

Enjoy serene waterfront views and easy access to moorings and facilities.

"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"

Enjoy cooking in this well-equipped kitchen with a double oven, large refrigerator, and shelf.

"It was a great stay!"

Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a skylight above.

"Very clean beautiful house! We stayed there for a wedding weekend and it was perfect. Great location. The hosts were wonderful and got back to us right away! Would love to go back one day."

Guests gather at the ceremony site, surrounded by lush greenery and a serene water view.

"Overall this was the most amazing experience from the location and the house itself to the property manager. The property manager was so amazing and made sure that if you needed anything in your stay they would make it happen. They were also very good about communication and responding quickly. On top of all of this the house itself is amazing and in the perfect location. Whether you want to have a chill getaway or explore Annapolis and the other amazing locations around it is the perfect house."

"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. "

includes taxes & fees

30 July - 31 July

Overlooking the marina, the city skyline shines brightly.

"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."

includes taxes & fees

27 July - 28 July

Boats docked at the marina, surrounded by calm waters and a picturesque view.

"Such a cute and unique place to stay. Very peaceful. "

Enjoy a serene view of the water from this deck, surrounded by lush greenery and a comfortable seating area.

"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"

"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."

includes taxes & fees

25 Aug - 26 Aug

Guests can enjoy serene waterfront views from the end of the pier, where two Adirondack chairs await.

"We had a wonderful long weekend here. Perfect weather let us swim and kayak and fish all weekend. House was spacious enough for two families of five plus our dog. The views were perfect!"

Relax in a serene park setting surrounded by lush greenery and a central gazebo.

"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"

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Top Calvert County Hotel Reviews

Days Inn by Wyndham Lanham Washington DC

10/10 Excellent

"Will strongly recommend this property. "

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Great location and close to great restaurants. While pet friendly it was difficult to find a doggy potty area. The bathroom had had a leak that was barely patched and the bath had no fan. The parking was valet and we thought our car was parked in an enclosed area but we later saw it in a school parking lot."

Historic Inns of Annapolis

10/10 Excellent

"This property is perfectly located within short walking distance of the USNA, downtown shopping/dining and the State House. It could not be in a better location. The property is historic, beautiful and well maintained. The room was spacious, clean and did not feel tired or in need of a refresh. We were absolutely thrilled with the property and will stay here every time we are back in town."

Find out more about Calvert County

Everything you need to know about Calvert County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Calvert County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Calvert County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Calvert County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Calvert County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Calvert County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Calvert County holiday rentals we have chosen for you start as low as AU$407 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Calvert County rentals

At Expedia, we put the best Calvert County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Calvert County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Calvert County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Calvert County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Calvert County Holiday Rentals

Change your mind

Treat yourself

Be picky

Top Holiday Rentals Destinations in Calvert County

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

The Cozy Crab- Your Charming Haven in Lovely North Beach!

Waterfront Solomons Apartment

Maryland Vacation Rental w/ Private Pool & Dock

Sweet Bamboo Beach Cottage

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

Floating 2 bed 2 bath condo stunning views of the bay

Waterfront Cottage in Beautiful Hoopers Island

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

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

Quiet Relaxing Waterfront Suisse Chalet

Waterfront Getaway, Dock Your Boat & Play!

Relax on Kent Island in 3 Bedroom Home w/Waterview

Chesapeake Houseboat Getaway on Kent Island, Maryland

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

Edgewater/Mayo Gateaway w/ Hot Tub

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

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

Top Calvert County Hotel Reviews

Days Inn by Wyndham Lanham Washington DC

Harborside Hotel

Annapolis Waterfront Hotel, Autograph Collection

Historic Inns of Annapolis

The Westin Washington National Harbor

Holiday Inn Express Washington DC East - Andrews AFB by IHG

Country Inn & Suites by Radisson, Annapolis, MD

Rod 'N' Reel Resort

DoubleTree by Hilton Hotel Annapolis

Find out more about Calvert County