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Tilghman Vacation Rentals

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Browse Select Tilghman Vacation Homes

Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (26)
"Great house and location. Very family friendly! "
The price is CA $373
CA $699 total
includes taxes & fees
Sep 25 - Sep 26
Beautiful Waterfront Retreat in Cambridge!
Walk to Everything House
Fridge, microwave, oven, stovetop
Walk to Everything House
10.0 out of 10, Exceptional, (67)
"We enjoyed this lovely historic home that is a short walk to attractions in St Michaels. It has a nice patio out back and is very close to a coffee shop."
Walk to Everything House
Blocks to the Boardwalk!
Beach nearby, sun loungers, beach towels
Blocks to the Boardwalk!
9.8 out of 10, Exceptional, (31)
"We had fun"
Blocks to the Boardwalk!
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
10.0 out of 10, Exceptional, (5)
"Our stay here with Brenda was amazing! She was very pleasant and professional! She even suggested a few things for us to do in the area. The home had everything we could have needed and wanted. The place looks even better in person than the pictures! We can’t wait to book again!"
The price is CA $237
CA $450 total
includes taxes & fees
Sep 24 - Sep 25
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
River Front, Private Single Family Home
Property grounds
River Front, Private Single Family Home
10.0 out of 10, Exceptional, (4)
" If I could give a 10 star rating I would! Host was very responsive to inquiries. Place was clean and peaceful. Tucked away in its little community, yet minutes to anything you could need or want. Pictures are accurate. The view is beautiful. Would definitely book again. "
River Front, Private Single Family Home
Waterfront Cottage on the Eastern Shore
Fridge, microwave, oven, stovetop
Waterfront Cottage on the Eastern Shore
9.6 out of 10, Exceptional, (7)
"We rented the house for the weekend and to host a surprise birthday party. We had the party right at the beach and the host/concierge were able to help us with everything we needed. They really went out of their way for us, and it made a huge difference in the party’s success! Plus, you can’t beat the view and the Chesapeake Bay sunsets !!"
The price is CA $474
CA $1,111 total
includes taxes & fees
Oct 1 - Oct 2
Waterfront Cottage on the Eastern Shore
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (29)
"Perfect for a 3 day visit! "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Dollhouse in Central Historic St Michaels
Exterior
Dollhouse in Central Historic St Michaels
9.6 out of 10, Exceptional, (44)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Property grounds
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
10.0 out of 10, Exceptional, (4)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is CA $237
CA $535 total
includes taxes & fees
Sep 24 - Sep 25
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Beach nearby
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
9.6 out of 10, Exceptional, (39)
"I was very impressed with this property. It's a cute little house that was comfortable for our group of 6. It was at a great location, too. The owner was quick to respond to my questions. If we visit North Beach again, I will definitely book here again."
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Beach nearby, sun loungers, beach towels
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
10.0 out of 10, Exceptional, (89)
"It was nice to get outside DTA and see another part of Annapolis. 15 minutes from DTA it was quiet and beautiful small cottage perfect for our family. The home was clean and designed well. We would stay again. Thank you!!!"
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Pet-Friendly Annapolis Home: Walk to Beach!
Beach nearby
Pet-Friendly Annapolis Home: Walk to Beach!
Pet-Friendly Annapolis Home: Walk to Beach!
Charming Annapolis WaterVIEW Home
Property grounds
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (47)
"Great house qoth ocean view"
Charming Annapolis WaterVIEW Home
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (14)
"Amazing time with friends and family at this property. I just need to remember to buy more bug spray haha. Regardless though- it was worth it"
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Lake
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (70)
"We enjoyed our stay a great deal. Jon is a great host, the house was comfortable and spacious, and the view of the night sky from the pier was spectacular."
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Circa 1700 Chesapeake Colonial home on the National Register.
Exterior
Circa 1700 Chesapeake Colonial home on the National Register.
9.8 out of 10, Exceptional, (49)
"We very much enjoyed our stay, relishing the peace and quiet of the property as an offset to our busy wedding week. The house was spacious and well outfitted, and we all enjoyed downtime in the pool. Glen was very helpful at answering all of our questions. We left the galley stairs to the young adults traveling with us. :)"
Circa 1700 Chesapeake Colonial home on the National Register.
Steps to the marinas with Private back deck, yard and Easy parking
Property grounds
Steps to the marinas with Private back deck, yard and Easy parking
10.0 out of 10, Exceptional, (31)
"Five star"
Steps to the marinas with Private back deck, yard and Easy parking
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (33)
"A perfect escape from city living! Clean property, easy to access kayaks and canoe for wonderful paddling right from the dock and a great fire pit in the yard. So peaceful. The bathrooms were clean and inviting after a day on the water. The kitchen had everything needed to help enjoy a cooked meal of fresh veggies from nearby Emily’s Produce (BIG recommendation!). Thank you"
The price is CA $312
CA $378 total
includes taxes & fees
Oct 15 - Oct 16
Waterfront Getaway with Dock
BeachWalk Cottage - Charm by the Chesapeake Bay
Beach
BeachWalk Cottage - Charm by the Chesapeake Bay
9.8 out of 10, Exceptional, (81)
"This beach cottage was just what our family, pup included, needed for a long weekend getaway! The furnishings were nice and comfortable. We discovered the beach toys on the second day and my son loved being able to build a sand castle. There were a few minor things that would have made the stay even better: the back sliding door was very difficult to open/close and there was no soap for the dishwasher."
BeachWalk Cottage - Charm by the Chesapeake Bay
New! Stylish downtown home w/awesome outdoor area!
Property grounds
New! Stylish downtown home w/awesome outdoor area!
10.0 out of 10, Exceptional, (17)
"The owners have the gift of hospitality. Easy check in/out, clean!!, handsome decor, lovely setting and room for everyone."
The price is CA $332
CA $728 total
includes taxes & fees
Sep 30 - Oct 1
New! Stylish downtown home w/awesome outdoor area!
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Other property types in Tilghman

Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
Fridge, microwave, oven, stovetop
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
9.4 out of 10, Exceptional, (6)
"The home was beautiful, the indoor pool was great Everything about the home was perfect for our family vacation (4generations). The only thing that was not enjoyable was the flooding caused by hurricane Debby but it did leave us with memories. . Eastern Shores is a great host and kept us informed "
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (83)
"The house was clean and comfortable. Walking distance to a local restaurant. Screened porch was great for watching the sunrise in the morning and the boats coming in and out of harbor "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Cass-Away Luxury Houseboat
Smart TV
Cass-Away Luxury Houseboat
10.0 out of 10, Exceptional, (87)
"All as advertised Wonderful option to a hotel"
The price is CA $190
CA $475 total
includes taxes & fees
Sep 26 - Sep 27
Cass-Away Luxury Houseboat
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.