Updating...
Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview
Wittman log cabin
- 5 bedrooms
- 5 bathrooms
- sleeps 10
Price per night from
$1,121
Location Location! St Michaels-- In Town Cottage!
St. Michaels house
- 2 bedrooms
- 2 bathrooms
- sleeps 5
Price per night from
$353
Waterfront Property, Kayaks, Private Dock, Near Town
St. Michaels house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
Price per night from
$863
Price per night from
$383
Price per night from
$6,898
St. Michael's Premier in Town Summer Cottage now with private pool!
St. Michaels house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Price per night from
$719
Responds fast! avg. 38 minutes
Price per night from
$2,300
CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Sherwood house
- 8 bedrooms
- 10 bathrooms
- sleeps 12
Responds fast! avg. 38 minutes
Price per night from
$2,875
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
St. Michaels house
- 6 bedrooms
- 6 bathrooms
- sleeps 12
Responds fast! avg. 38 minutes
Price per night from
$2,300
Price per night from
$1,897
Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities
Royal Oak manor house
- 25 bedrooms
- 25 bathrooms
- sleeps 50
Price per night from
$7,473
Great rentals within 20 miles that match your search
“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.
Price per night from
$460
Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)
Chester house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.
Price per night from
$455
Vintage Bungalow-cozy, walk to shops, water, free pkg.
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$478
Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can
Stevensville house
- 4 bedrooms
- 2 bathrooms
- sleeps 12
Price per night from
$805
KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12
Kent Island house
- 4 bedrooms
- 2 bathrooms
- sleeps 12
Price per night from
$1,955
DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12
Chester house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
Price per night from
$1,955
Price per night from
$1,150
Price per night from
$276
Price per night from
$402
Price per night from
$403
Price per night from
$443
Price per night from
$229
Price per night from
$344
Price per night from
$574
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis apartment
- 2 bedrooms
- 1 bathroom
- sleeps 6
Price per night from
$225
Price per night from
$684
Price per night from
$673
Price per night from
$249
Price per night from
$345
Price per night from
$190
Price per night from
$229
Price per night from
$804
Bay Ridge house by Quiet Waters Park, Thomas Point Park
Annapolis apartment
- 2 bedrooms
- 1 bathroom
- sleeps 5
Price per night from
$225
Price per night from
$432
Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
Chester house
- 4 bedrooms
- 3 bathrooms
- sleeps 12
Price per night from
$460
Viewing 38 of 77
rentals in Talbot County
Top Destination reviews
Also consider
- St. Michaels 7 properties
- Ocean City 148 properties
- Baltimore 70 properties
- Annapolis 66 properties
- Montgomery County 47 properties
- North East 46 properties
- National Harbor 13 properties
- Kent Island 11 properties
- Ocean Pines 10 properties
- Calvert County 10 properties
- Glen Burnie 9 properties
- Edgewater 9 properties
- Oxon Hill 8 properties
- Mount Rainier 7 properties
- Rosedale 7 properties
- Severna Park 7 properties
- Fort Washington 5 properties
- Marion Station 5 properties
- Suitland 5 properties
- Hampden 5 properties
- Parkville 5 properties
- Chillum 5 properties
- Garrett County 5 properties
- Arizona 1,727 properties
- Missouri 1,493 properties
- Alabama 1,139 properties
- Ohio 536 properties
- Indiana 261 properties
- Kentucky 256 properties
- Minnesota 208 properties
- Iowa 84 properties
- Nebraska 35 properties