Talbot County Holiday Rentals

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Featured Talbot County Holiday Rentals

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (119)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (40)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Waterfront Property, kayaks, private dock, near town

9.8 out of 10, Exceptional, (151)
"Very nice place! Everything was perfect! Lisa is a great host! Our plane was cancelled so she let us extend our stay free of charge! We will be back!! Thanks Lisa!"
Waterfront Property, kayaks, private dock, near town

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (73)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is HK$2,119
HK$3,884 total
includes taxes & fees
1 Jul - 2 Jul
Waterfront Oasis of Annapolis Star

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (165)
"The Waterfront Retreat on the Patuxent River is better than advertised. Our whole family stayed -- everyone loved it! It was clean, comfortable, with everything needed to stay comfortably, sleep, eat, relax and use as a home base for exploring. Solomons Island and the surrounding area was filled with lots of fun things to do (restaurant's, museums, history, boating, walking, etc.). "
Waterfront Wildlife Retreat on the Patuxent River

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (224)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (32)
"Great location, close to the beach and restaurant. Cozy and comfortable, with a beautiful view of sunset. "
Chesapeake Houseboat Getaway on Kent Island, Maryland

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

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

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (29)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Private Cottage on gated estate

10.0 out of 10, Exceptional, (24)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (248)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (37)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is HK$1,113
HK$2,727 total
includes taxes & fees
6 Jul - 7 Jul
Relax on Kent Island in 3 Bedroom Home w/Waterview

Waterfront Solomons Apartment

9.4 out of 10, Exceptional, (9)
"The location is great with amazing views of the docks and very walkable to the boardwalk, restaurants, and the Solomon museum. Apartment was cozy with great communication from the hosts. Would recommend to anyone! "
The price is HK$1,060
HK$2,130 total
includes taxes & fees
6 Jul - 7 Jul
Waterfront Solomons Apartment

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (62)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (41)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
8.0 out of 10, Very good, (4)
"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

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (36)
"Was a great vacation hope to come back next year!"
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

10.0 out of 10, Exceptional, (37)
"Loved the location and the pristine condition of the house. "
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is HK$1,554
HK$3,517 total
includes taxes & fees
9 Jul - 10 Jul
The Cottage

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (47)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
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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