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Vacation Rentals in Tilghman Island, Maryland

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Tilghman Island vacation rentals

Tilghman Island on Maryland's Eastern Shore is surrounded by the beautiful Chesapeake Bay.  The island is separated from the mainland by Knapps Narrows and is accessed by drawbridge. Tilghman Island is a waterman's village — home to the last commercial sailing fleet in the U.S, the Skipjacks, which can be viewed at Dogwood Harbor. Many recreational activities are available on and offshore the island, including duck hunting, fishing, lighthouse tours by boat, sailing, and walking tours. Phillips Wharf Environmental Center offers touch tanks where you can get close to sea creatures, and Tilghman Waterman’s Museum preserves artifacts related to the role of Tilghman's Island in the history of the Chesapeake Bay. Tilghman Island Vacation Rentals are plentiful and affordable and are one of the best methods of securing Tilghman Island Deals. You can increase your Tilghman Island Savings even further by searching for Tilghman Island Last Minute Deals.

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Charming Island Home on Chesapeake Bay with Great Water Views
Tilghman Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $185 - $350 /nt
    $1,225 - $1,295 /wk
 
 
 
 
 

2 reviews write a review

It's all about the view! Updated, decks, shaded back yard, hot tub
Tilghman Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $520 - $641 /nt
    $2,015 - $2,720 /wk
 
 
 
 
 

13 reviews write a review

Lovingly restored authentic 1920's waterman's cottage with wide bay views
Tilghman Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $333 - $440 /nt
    $1,515 - $2,095 /wk
 
 
 
 
 

70 reviews write a review

Pool, hot tub, big water views - what more could you ask for in a cottage!
Tilghman Island Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 7
  • baths 3
  • rates (USD) $443 - $685 /nt
    $1,905 - $3,515 /wk
    $14,108 /mth
 
 
 
 
 

45 reviews write a review

Duck Cove - A Crabbers Cottage Gone Upscale
Tilghman Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $328 - $415 /nt
    $1,355 - $1,874 /wk
 
 
 
 
 

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Friends & Family "Crash Pad" - Views, Pool, Kayaks, Bikes, Firepit & More
Tilghman Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $521 - $783 /nt
    $2,092 - $3,897 /wk
 
 
 
 
 

15 reviews write a review

Gracious waterfront home! Prime Summer Weeks Still Available!
Tilghman Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 9
  • baths 3
  • rates (USD) $517 - $998 /nt
    $3,087 - $5,771 /wk
 
 
 
 
 

2 reviews write a review

Premium Waterfront Estate Property - $7,500/Week -
Tilghman Island Estate Rental Picture
  • bedrooms 5
  • rental type Estate
  • owner badgeowner badge
  • sleeps 10
  • baths 7
  • rates (USD) $1,200 /nt
    $7,500 /wk
 
 
 
 
 

12 reviews write a review

Waterfront Tilghman Island Cottage
Tilghman Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $75 - $175 /nt
    $500 - $800 /wk
    $1,500 - $2,000 /mth
 
 
 
 
 

2 reviews write a review

Knapps Narrows Waterfront Getaway W/ Boatslip!
Tilghman Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD) $300 - $375 /nt
    $1,890 - $2,450 /wk
 
 
 
 
 

8 reviews write a review

Tilghman Island Cottage for 6 - Still Available July 19-26
Tilghman Island Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 6
  • baths 2
  • rates (USD) $136 - $175 /nt
    $750 - $950 /wk
    $1,100 - $3,500 /mth
 
 
 
 
 

6 reviews write a review

Tilghman Island Dreamin. A Beautiful Home Overlooking Dogwood Harbor
Tilghman Island Villa Rental Picture
  • bedrooms 4
  • rental type Villa
  • sleeps 10
  • baths
  • rates (USD) $200 - $250 /nt
 
 
 
 
 

2 reviews write a review

Large Waterfront House Near St. Michael's with Pool & Dock
Tilghman Island House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $400 - $600 /nt
    $4,200 /wk
 
 
 
 
 

1 reviews write a review