Updating...
Responds fast! avg. 3 hours 9 minutes
Price per night from
$86
Indoor pool and spa located in beautiful Southern Maryland woodlands
Chesapeake Beach house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
Price per night from
$1,105
Responds fast! avg. 2 hours 41 minutes
Price per night from
$67
Delightful Pet Friendly Family Home In Great Location
Huntingtown house
- 4 bedrooms
- 2 bathrooms
- sleeps 9
Responds fast! avg. 3 hours 35 minutes
Price per night from
$240
Price per night from
$149
Blue Pearl - Life on the River! Luxury estate with jacuzzi and private pier!
Broomes Island house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
Price per night from
$400
Quiet Cottage, Hot Tub, Bay View, Block to Beach, 1hr to DC
Saint Leonard house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Price per night from
$251
Great rentals within 20 miles that match your search
CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Sherwood house
- 8 bedrooms
- 10 bathrooms
- sleeps 12
Price per night from
$2,864
Private Waterview Gladstone Manor with 4 Master Suites
Shady Side house
- 6 bedrooms
- 7 bathrooms
- sleeps 14
Responds fast! avg. 2 hours 27 minutes
Price per night from
$429
“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
$1,890
Price per night from
$155
Price per night from
$682
Cozy cottage with expansive backyard and firepit!
Tracys Landing house
- 2 bedrooms
- 1 bathroom
- sleeps 4
Price per night from
$287
Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths
Cambridge house
- 6 bedrooms
- 5 bathrooms
- sleeps 18
“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
$1,030