Calvert County Rentals

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Price: high to low

Number of reviews

15 Houses

Chesapeake Beach Apt. Walk to Bay, Beach & Marina!

Chesapeake Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$81

Harbor Cottage at the Chesapeake Bay

Saint Leonard cottage

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$298

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$580

Renovated Luxury Waterview House

North Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$346

Business or Leisure?

Lusby guest house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 4 minutes

Price per night from

$75

St. Leonard Cottage w/Pool Overlooking Wells Cove!

Saint Leonard cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$103

Indoor pool and spa located in beautiful Southern Maryland woodlands

Chesapeake Beach house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$573

Modern Luxury Rental in North Beach!

North Beach house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$155

Quiet cottage on wooded property

Lusby bungalow

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 46 minutes

Price per night from

$67

Great rentals within 20 miles that match your search

Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths

Cambridge house

6 bedrooms / 5 bathrooms / sleeps 20

“Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was clean and well furnished. The dining room table and table on the porch provided plenty of seating for meals. There was plenty of hot water for showers and clean-up after meals. The pool was clean and the river was awesome, with a gradual slope that was perfect for kids and adults. We used the crab traps provided and caught 2 dozen crabs that made a great contribution to dinner on Friday. Crabbing was best by the dock. We caught all but 3 crabs there, rather than out closer to the middle of the river. The AC on the ground floor stopped working on Tuesday, but one call to the owner and the repair team was on-site in less than 2 hours. The issue was resolved before noon on Wednesday. We have been renting vacation properties for years and issues crop up from time to time. We appreciated the quick response and resolution. The one recommendation we will make is to bring bug spray (mosquitos and horse flies). We anticipated it being right on the river, but if you haven't had that experience, you need to be prepared.

Price per night from

$748

Private 2 Bedroom Apartment

Waldorf apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$115

Deerpond Carriage House

Woolford guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$207

A Special Occasion Property

Croom house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 41 minutes

Price per night from

$287

Year Round Estate on Bay / Fam. Reunions / Slps 28

Cambridge house

7 bedrooms / 7 bathrooms / sleeps 28

“Unbelievable Home in an Unbelievable Setting!!!” Our family cant thank you enough for the memories made at captains quarters this summer. This was the first time getting away with the entire family (kids grandkids, grand parents, etc) and it was propabaly the most memorable week our family has ever spent together. The house was absolutely perfect! Clean, beautifully furnished, amenities for all ages and the most spectacular grounds and views for the entire family to enjoy. We are already planning our stay for next summer and hope to come back this winter as well for a long weekend. Thank you thank you thank you!

Price per night from

$1,375

⟰Beautiful home, Quiet neighborhood, Home away from home⟰

Croom townhouse

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$126

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