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Calvert County Vacation Rentals

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Top cities in Calvert County

A coastal town with a marina, residential buildings, and a clear sky.
Vacation Rentals

Chesapeake Beach

Chesapeake Beach

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Calvert County vacation rentals

Living area

1. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $124
CA $420 total
includes taxes & fees
Nov 12 - Nov 13
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

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

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is CA $203
CA $438 total
includes taxes & fees
Nov 9 - Nov 10
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Downstairs living Space

3. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Very clean and nice property"
United States
Ben W.
The price is CA $201
CA $567 total
includes taxes & fees
Dec 2 - Dec 3
Family Beach House: Spacious Deck, Grill & Views
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

4. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is CA $212
CA $397 total
includes taxes & fees
Nov 16 - Nov 17
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

5. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
The price is CA $273
CA $557 total
includes taxes & fees
Nov 20 - Nov 21
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
A cozy outdoor seating area with a fire pit, a wooden table, and chairs.

6. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (40 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is CA $223
CA $639 total
includes taxes & fees
Dec 2 - Dec 3
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

7. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (68 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is CA $213
CA $423 total
includes taxes & fees
Nov 16 - Nov 17
Soul Oasis - home on the Chesapeake Bay
Fire pit (2)

8. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $399
CA $640 total
includes taxes & fees
Nov 8 - Nov 9
Plum Point Cottage #17
Fire pit (2)

9. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (10 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is CA $479
CA $757 total
includes taxes & fees
Nov 13 - Nov 14
Plum Point Cottage #14
Fire pit (2)

10. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is CA $478
CA $797 total
includes taxes & fees
Nov 8 - Nov 9
Plum Point Cottage #15
A pathway lined with trees and lights leading to a wooden building with a visible window.

11. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (15 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is CA $648
CA $1,149 total
includes taxes & fees
Nov 9 - Nov 10
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A spacious living room with a large sofa, a television, and a view of the ocean.

12. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is CA $421
CA $994 total
includes taxes & fees
Nov 9 - Nov 10
4-BR Waterfront Turret Home
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

13. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (4 reviews)
"Dude. This is what I always hope a rental property will be. Comfy beds, best stocked kitchen, working hot tub, beautiful waterfront area with kayaks and a dock. And our mini golden doodle could come too?! It was absolute perfection."
United States
Dani B.
The price is CA $493
CA $1,266 total
includes taxes & fees
Nov 10 - Nov 11
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

14. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is CA $607
CA $1,519 total
includes taxes & fees
Nov 9 - Nov 10
Lakefront Cabin Near Solomons Island w/ Hot Tub
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

15. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is CA $716
CA $1,604 total
includes taxes & fees
Nov 8 - Nov 9
Lakefront Cabin Near Solomons Island w/ Hot Tub
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

16. 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, (16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is CA $238
CA $388 total
includes taxes & fees
Nov 10 - Nov 11
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A lakeside view with chairs and a table, a rainbow, and trees.

17. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is CA $322
CA $513 total
includes taxes & fees
Nov 10 - Nov 11
Bright and airy waterfront getaway
A single-story house with a front porch, a small deck, and a number '4' on the side.

18. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
10.0 out of 10, Exceptional, (1 review)
"If you want a quiet slice of VA/Potomac waterfront, this is the place."
United States
John
The price is CA $215
CA $363 total
includes taxes & fees
Nov 9 - Nov 10
Coles Point Marina
A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

19. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is CA $135
CA $409 total
includes taxes & fees
Nov 10 - Nov 11
Charming Coastal/Country Home w/3 Acres & Sauna!
A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

20. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is CA $195
CA $481 total
includes taxes & fees
Nov 23 - Nov 24
Relax on Kent Island in 4 Bedroom Home w/Waterview
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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Apartments

Top Calvert County Hotel Reviews

A two-story house with a porch, a front door, and a small garden area.
The Wildset

The Wildset

The Wildset
Downtown St. Michaels

10/10 Excellent

Our stay at the Wildset was amazing! The room was beautiful and clean. The staff were available at all hours and did the most to ensure our stay was special. The hotel has lots of small touches that truly make the experience like bikes, a cafe with coffee and drinks, and smore's kits in the evenings.
Canada
Mairi
Reviewed August 11, 2026
The Wildset

Find out more about Calvert County

Everything you need to know about Calvert County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Calvert County vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Calvert County vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Calvert County vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Calvert County vacation rentals we have selected for you start as low as CA $214 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 vacation 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 vacation.

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.