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Holiday Homes in Tilghman

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Featured Holiday Homes in Tilghman

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

10.0 out of 10, Exceptional, (39)
"Loved the location and the pristine condition of the house. "
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (21)
"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."
Bay views with kayaks, bikes, fire pit, crabbing and more

Private Cottage on gated estate

10.0 out of 10, Exceptional, (28)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is AU$611
includes taxes & fees
22 Aug - 23 Aug
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (43)
"Our kids enjoyed the games in the crab house. It was great being able to use the kayaks and life vests."
The price is AU$735
includes taxes & fees
3 Sept - 4 Sept
Beautiful Waterfront Retreat in Cambridge!

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"I cannot say enough about this property. Home was so spacious, views were wonderful, kitchen was very well stocked and just minutes to town. Highly recommend renting this home."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (18)
"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "
River Front, Private Single Family Home

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

10.0 out of 10, Exceptional, (12)
"Very clean beautiful house! We stayed there for a wedding weekend and it was perfect. Great location. The hosts were wonderful and got back to us right away! Would love to go back one day."
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

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

9.8 out of 10, Exceptional, (46)
"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

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

9.4 out of 10, Exceptional, (6)
"Modern, Fresh, Clean! No complaints at all!"
The Cozy Crab- Your Charming Haven in Lovely North Beach!

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (26)
"Excellent property, great communication with the hosts. Quite and relaxing"
25-50% Off~Private Beach~Hot Tub~Fire Table~

Annapolis Home Near Beach & Quiet Waters Park!

Annapolis Home Near Beach & Quiet Waters Park!

Amazing views waterfront 3-bedroom home in Madison

9.6 out of 10, Exceptional, (5)
Amazing views waterfront 3-bedroom home in Madison

Searenity Stays, a Cozy Home

10.0 out of 10, Exceptional, (36)
"Our stay was very comfortable here. The kitchen was well stocked for cooking, the beds were comfortable, plenty of towels, and very clean. We would definitely stay here again."
Searenity Stays, a Cozy Home

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (55)
"Great and comfortable stay! Beautiful historic house and property Owners were so friendly and helpful"
Circa 1700 Chesapeake Colonial home on the National Register.

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (132)
"Great house, host and location. Stayed with a larger group and plenty of room!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (66)
"Came for a wedding at Herrington on the Bay which was only a 5 minute drive away. Short walk to the beach and many restaurants in North Beach. Great for 4 people."
The Blue Crab Beach House - Free beach passes

Walk to Everything House

10.0 out of 10, Exceptional, (81)
"Clean and nice place to stay"
Walk to Everything House

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

9.8 out of 10, Exceptional, (18)
"We wanted to celebrate Easter with our two daughters who go to Loyola in Baltimore so we decided to stay in Annapolis area. We absolutely loved the house. The location and view was amazing- right on the Chesapeake bay! The house was clean and welcoming. There were so many nice little touches that made us feel welcomed. We had a great weekend celebrating Easter with our two daughters and son. The house was the perfect size for the 5 of us. "
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (48)
"wonderful home and great views. Clean, quiet, plenty of amenities"
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
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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Top Tilghman Hotel Reviews