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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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Tilghman Island things to do


Sail Selina II

One of the main activities my friends and I wanted to partake in on our trip to St. Michael's was a sailing venture, which we ended up thoroughly more


Carpenter Street Saloon

Went in as a large group, and left reasonably happy with full stomachs. It is definitely a casual place, and it probably could use some sprucing up. more


St. Michaels Winery

I've been here twice. The more recent visit took place just two days ago. We had the dry red tasting, and unfortunately I did not find most of the wines more


Chesapeake Bay Maritime Museum

Awesome place to go for a weekend day trip that is for sure! I love this place - you can bring your own lunch or snacks in and eat along the more than more


Dockside Express

As the Maid of Honor it's my responsibility to ensure a good time is had by all! I was planning this bachelorette weekend from 640 miles away, having more


Tricycle and Run

I know enough about biking that I knew my girlfriend needed a seat upgrade after our 8 mile ride from Oxford to St. Michaels. She was not a happy camper more


Calico Gallery

Wow. This is like the BEST toy store I've ever seen. And it's not a chi-chi, "we're all wood and German-made and you're all Very Involved in more


Tilghman Island Marina

On a whim we rented a tandem kayak. The keener, Ron was very personable and eager to accommodate. He provided us with a map of trails. Equipment was in more


St. Michaels Concours d'Elegance

With the help of Cole Porter: It's delightful, it's delicious, it's d'Elegance You can tell at a glance what a swell event this is for romance You more


St. Michaels Marina

Funny time to write about a marina, but hey I forgot to do it in the summer. Although this place gets "props" for friendliness and proximity to town, more


Lady Patty Classic Yacht Charters

This was the best! The boat is from 1935, restored with love, but shows her age with great character. The price for a two-hour sail is reasonable, more


Country Comfort Farm

I want to start out by saying that I think this place is a perfectly respectable stables for boarding your horse, showing your horse, or retiring more


Feelin' Good Studio

I recently made the trip to St. Michael's for a workshop in Reflexology with Lara. The studio was lovely, clean and quiet. Lara was a great teacher and more

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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) $457 - $645 /nt
    $1,851 - $2,785 /wk

12 reviews write a review

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) $484 - $892 /nt
    $1,975 - $4,758 /wk

15 reviews write a review

Wide water views, bay breezes, a perfect bay-cation!
Tilghman Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 9
  • baths 3
  • rates (USD) $562 - $1,338 /nt
    $3,003 - $6,681 /wk

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Cozy winter hideaway with wide water views and new kitchen
Tilghman Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $425 - $581 /nt
    $1,670 - $2,537 /wk

67 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) $478 - $852 /nt
    $1,892 - $3,864 /wk

45 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)

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Knapps Narrows Waterfront Getaway W/ Boatslip!
Tilghman Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD) $275 - $375 /nt
    $1,645 - $2,450 /wk

6 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