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Compare 291 Vacation Homes in Tilghman with updated reviews, rates, and availability.

Caribbean Pool Home <1 mile from Matapeake Beach!
10.0 out of 10, Exceptional, 1 review
"The house was exactly as promised! We were very happy with the accommodations!"
The price is $446
$1,041 total
includes taxes & fees
Jun 9 - Jun 10
Caribbean Pool Home <1 mile from Matapeake Beach!
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, 27 reviews
"The house was perfect for our needs. It has a cute, fenced in yard so our 2 dogs could hang outside. It had everything we needed for a wonderful weekend birthday celebration!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, 102 reviews
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
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NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
10.0 out of 10, Exceptional, 9 reviews
"Our stay in Annapolis was a short and sweet 3-day visit for a wedding--my original focus was to have enough space for everyone to get ready without waiting in line. The property provided so much more than enough room. The entire house was very clean, well-appointed, and smartly laid out. The kitchen was stock with a wide range of food to get the weekend started off without the need to spend hours in the local grocery store. Throw in a great ping-pong table to make it even more fun. My only two...
NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, 4 reviews
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
9.6 out of 10, Exceptional, 12 reviews
"Our stay in Oyster Harbor was very nice. The weather didn't cooperate but the house itself was very nice and I would certainly stay there again. It's about a 10 minute drive to downtown Annapolis so that made it convenient as well!"
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
The Lazy Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, 25 reviews
"Everything was perfect and the host was very kind! Would definitely recommend, especially for anyone staying in the area for a wedding."
The Lazy Crab Beach House - Free beach passes
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
9.6 out of 10, Exceptional, 35 reviews
"Great place for a short moms getaway. Walking distances to many things. Heard live music from the porch. House is spacious and extremely clean"
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Blocks to the Boardwalk!
9.8 out of 10, Exceptional, 27 reviews
"The house was in the perfect locatfor us and our two dogs. Tammy was always available to answer our questions, very approachable and professional. We highly recommend this property to anyone."
Blocks to the Boardwalk!
Private Waterview Estate with 4 bedroom Suites & Hot Tub
9.8 out of 10, Exceptional, 18 reviews
"Great location and house! We all had a great time!"
Private Waterview Estate with 4 bedroom Suites & Hot Tub
Newly Remodeled Home, 10 Minute Walk to Downtown
10.0 out of 10, Exceptional, 5 reviews
"Very clean house with comfortable beds. Enjoyed our stay!"
Newly Remodeled Home, 10 Minute Walk to Downtown
Grace Cottage, Saint Michaels Walk to everything!
10.0 out of 10, Exceptional, 1 review
"Beautiful house. Great location. Host was very responsive to questions. Thanks for a great stay"
Grace Cottage, Saint Michaels Walk to everything!
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton
9.6 out of 10, Exceptional, 66 reviews
"we had a business trip up in MD - had 8 guys up there with the owner of the company and everyone was very comfortable. The rental property let us know that the pool was closed, but it all worked out great cause the weather was awful. The property/house was fantastic for the 8 of us. Space wise and sleeping it was perfect. Thank you."
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! No cleaning fee!
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! No cleaning fee!
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
The price is $499
$846 total
includes taxes & fees
Jun 6 - Jun 7
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Charmingly restored, dog-friendly retreat with great deck & walkable location
10.0 out of 10, Exceptional, 1 review
Charmingly restored, dog-friendly retreat with great deck & walkable location
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, 21 reviews
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, 25 reviews
"I chose to stay at this property for the duration of my wedding weekend. It was really great to be able to spend that extra time with family all together! Getting ready at the house, rather than a hotel was also really nice because we had much more room to space out. The make up artist and hair stylist also complimented the ample natural light and space to work. The pool and hot tub were beautiful! The only downside was a lack of curtains in the master bedroom. The sunrise is beautiful but...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, 74 reviews
"The cottage provides a wonderful way to experience Deale and the surrounding area. Well equipped and clean, I had everything I needed and didn't want to leave,"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
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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.

Other property types in Tilghman

Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
9.4 out of 10, Exceptional, 3 reviews
"We enjoyed a long weekend at this property. The location being right on the water made the views incredible. We unfortunately were there during a rainy weekend, but the indoor pool saved us for sure. The main living areas of this property are gorgeous (kitchen, multiple living rooms). The furniture in the living rooms though are low to the ground, which was a challenge for the age 65+ individuals in our group. The bedrooms were nice and beds were super comfortable. Three of the five showers were...
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, 21 reviews
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, 102 reviews
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
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.

Tilghman Vacation Homes information

Number of reviews
422
Accommodation
291 Vacation Homes
Lowest Price
$446
Highest Price
$499

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