Calvert County Holiday Rentals

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Top Holiday Rentals Destinations 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
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Outdoor dining

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

9.6 out of 10, Exceptional, (9)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
The Cozy Crab- Your Charming Haven in Lovely North Beach!
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)
"We once again enjoyed our stay here. Perfect location to every where you’d want to go in St. Michael’s! Loved sitting out front looking at the water and park and enjoying music from our front yard. Highly recommend this cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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 AU$492
includes taxes & fees
28 Sept - 29 Sept
Waterfront Getaway, Dock Your Boat & Play!
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
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, (14)
"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"
The price is AU$1,918
includes taxes & fees
13 Oct - 14 Oct
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
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.
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
Riverfront Retreat 7mil from MD Renaissance Fest!
Exterior

Riverfront Retreat 7mil from MD Renaissance Fest!

9.2 out of 10, Wonderful, (17)
"It was a beautiful and private setting for a family reunion."
Riverfront Retreat 7mil from MD Renaissance Fest!
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (122)
"We are not strangers to the area, my wife having grown up in the area, but each time we stay on the Chesapeake we feel at home. The Hideaway is so nice that you don't want to go back your actual home! It is furnished as if it is a year-round residence, no cheap or mismatched furniture and appliances. We enjoy cooking and the kitchen is has everything you need and it works. The yard and amenities are top notch. If you enjoy bird watching, sit in the back yard and take in the bird activity...
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
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, (147)
"We enjoyed our stay at the waterfront cottage with yoga on the dock in the morning, afternoon kayaking and dinner at Captain Billy’s Seafood restaurant. Down time spent reading and nature watching made the for the perfect weekend."
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior detail

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

10.0 out of 10, Exceptional, (11)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Quaint 3/2.5 home in Fort Dupont
Private kitchen

Quaint 3/2.5 home in Fort Dupont

7.4 out of 10, Good, (24)
"The house was clean and close to where I needed to go. We will be back. "
The price is AU$408
includes taxes & fees
29 Sept - 30 Sept
Quaint 3/2.5 home in Fort Dupont
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (257)
"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
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 AU$179
includes taxes & fees
2 Oct - 3 Oct
Charming townhome with AC and WiFi in delightful Annapolis
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, (8)
Tiny, Funky, and Full of Love - Welcome to the Love Shack
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, (33)
"Accommodations as depicted, close to the Metro, nice neighborhood "
The price is AU$1,073
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
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Interior

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

10.0 out of 10, Exceptional, (53)
"My wife and I have stayed at many different places over the years but this may be one of the most well maintained properties I've ever seen. It was a great place for us to unwind with our dog and we would certainly recommend this location for anyone looking to stay in the area"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
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 Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent
"Nice"
Hun Chuan 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Largo/Washington DC

Find out more about Calvert County

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$179 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.