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Search Vacation Homes in Tilghman

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Oct 3 - Oct 5

Vacation Homes in Tilghman

Heated pool, sandy beach, pier, and playground set punch point apart!
Relax in Adirondack chairs along the serene lakeside, with a boat available for recreation.

Heated pool, sandy beach, pier, and playground set punch point apart!

10.0 out of 10, Exceptional, (9)
"Beautifully decorated, peaceful, well appointed home for our girls bday celebration. Highly recommend."
Heated pool, sandy beach, pier, and playground set punch point apart!
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Guests can enjoy a serene waterfront view from this tranquil pier.

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
Rising Sun Bay View Cottage
Relax in a serene outdoor space with a bench, table, and rocking chair, surrounded by a playground and lush views.

Rising Sun Bay View Cottage

10.0 out of 10, Exceptional, (1)
"What a great location for an awesome vacation rental. The three floors of the house is amazing and the views of the bay a huge added bonus. The house is well equipped, and you can tell that the owners stay there part time.The layout allows for socializing and fun on the middle level with a sitting areas and screened in porch while others can find some peace and quiet if needed on the upper or lower floorsThe private beach access is awesome and a true benefit. Will look to find this place again...
Rising Sun Bay View Cottage
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Enjoy a serene view of the water from this deck, surrounded by lush greenery and a comfortable seating area.

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

9.8 out of 10, Exceptional, (44)
"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
Relax on Kent Island in 3 Bedroom Home w/Waterview
Overlooking the marina, the city skyline shines brightly.

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
$313 nightly
The price is $332
Aug 27 - Aug 28
Total includes taxes and fees
Relax on Kent Island in 3 Bedroom Home w/Waterview
Bay views with kayaks, bikes, fire pit, crabbing and more
Enjoy cooking and dining in this well-equipped kitchen with appliances and a central island.

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
Edgewater/Mayo Gateaway w/ Hot Tub
Fridge, microwave, oven, stovetop

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (20)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
$529 nightly
The price is $566
Aug 18 - Aug 19
Total includes taxes and fees
Edgewater/Mayo Gateaway w/ Hot Tub
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Guests can enjoy serene waterfront views from the end of the pier, where two Adirondack chairs await.

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

9.8 out of 10, Exceptional, (129)
"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
St. Michaels Waterfront Home
Relax by the serene lake with a dock and a small boat, surrounded by lush greenery and comfortable Adirondack chairs.

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (31)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Kitchen features a stove, oven, microwave, and large island with seating.

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
The Blue Crab Beach House - Free beach passes
Relax on the beach with a serene view of the ocean from the pier's benches and gazebo.

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
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Enjoy a room with a sliding glass door leading to a balcony offering a water view.

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

9.8 out of 10, Exceptional, (17)
"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
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Stroll along the pier, taking in the serene coastal views and tranquil atmosphere.

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (120)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Boats docked at the marina, offering scenic views of the calm water.

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. "
$472 nightly
The price is $500
Sep 8 - Sep 9
Total includes taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and microwave, and dine at the wooden table.

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

9.8 out of 10, Exceptional, (40)
"Property was perfect for our family stay. House was clean and well stocked."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Beautiful Waterfront Retreat in Cambridge!
Relax in this cozy room with a bar area featuring a large window offering a view of the outdoors.

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (42)
"Our kids enjoyed the games in the crab house. It was great being able to use the kayaks and life vests."
$465 nightly
The price is $492
Aug 13 - Aug 14
Total includes taxes and fees
Beautiful Waterfront Retreat in Cambridge!
Waterfront Sunset Bayview: sleeps 6
Guests can enjoy serene waterfront views from the end of the pier, where two Adirondack chairs await.

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (19)
"Loved the location, the property, and amenities. Would definitely stay again!"
Waterfront Sunset Bayview: sleeps 6
Waterfront 3-Bedroom Cottage and Pet Friendly
Enjoy a meal or drink with a view of the sea from this dining area.

Waterfront 3-Bedroom Cottage and Pet Friendly

10.0 out of 10, Exceptional, (32)
"This beautiful home was wonderful for our long overdue vacation - We loved our stay here very much - The town is amazing "
Waterfront 3-Bedroom Cottage and Pet Friendly
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Enjoy a tranquil beachside setting with picnic tables, a playground and a pier extending into the water.

Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

10.0 out of 10, Exceptional, (93)
"Great property and great time in Oyster Harbour!"
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Waterfront Home w/ Hot Tub in Bozman Village!
Fridge, microwave, stovetop, dishwasher

Waterfront Home w/ Hot Tub in Bozman Village!

Waterfront Home w/ Hot Tub in Bozman Village!
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

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"I like the location and how easy it is to get to our room."
Rhonda 1-night trip
Posted 19 hours ago
Best Western Kent Narrows Inn