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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

This was by far the best part of our amazing trip to St. Michael's. We went on the champagne cruise. The boat is beautiful. The views were breathtaking. The...read more

 

Carpenter Street Saloon

Some of the other reviews sum the experience up pretty well. The atmosphere and service are definitely laid back and I certainly wouldn't recommend...read more

 

Lady Patty Classic Yacht Charters

Worth every minute, captain Jeff and first mate pj were very friendly and knowledgable . Great margaritas and the boat is beautiful. Can't wait to go again.read more

 

Chesapeake Bay Maritime Museum

YES! This is a fabulous museum for any age group, with plenty of hands-on activities to keep people interested and really enhance the learning. I hadn't...read 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 to...read 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 never...read more

 

Tricycle and Run

My wife and I were biking around St. Michael's on Memorial Day, and my wife's bike seat broke. I called Tricycle and Run to see if they were open and could...read more

 

Calico Toys and Games

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 Your...read 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 good...read 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 can...read more

 

Shore Pedal & Paddle

With a variety of options available, this shop has something for everyone. The equipment is well maintained. The staff well versed in all matters...read 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,...read more

 

Frivolous Fibers

A lovely shop for spinners, knitters and crochet enthusiasts. The shop is well stocked with a variety of fibers including a few locally grown specialities...read 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 your...read 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 made...read more

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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

Duck Cove - A Crabbers Cottage Gone Upscale nestled in Neavitt Village
Tilghman Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $361 - $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) $572 - $783 /nt
    $2,092 - $3,897 /wk
 
 
 
 
 

16 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) $602 - $984 /nt
    $3,087 - $5,771 /wk
 
 
 
 
 

2 reviews write a review

It's all about the view! Decks, shaded back yard, hot tub, Sunsets
Tilghman Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $568 - $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) $374 - $440 /nt
    $1,515 - $2,095 /wk
 
 
 
 
 

71 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) $490 - $685 /nt
    $1,905 - $3,515 /wk
 
 
 
 
 

45 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

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

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

Tilghman Island Cottage for 6 - Across from Marina and Knapps Narrows
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