Vacation rentals in Tilghman Island, MD

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Best Vacation rentals and Airbnb offers in Tilghman Island, MD

Tilghman Island Retreat By Knapps Narrows! - Tilghman Island, MD

Tilghman Island Retreat By Knapps Narrows!

Cottage, Tilghman Island

Tilghman Island Retreat By Knapps Narrows! is a cottage in Tilghman Island, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Tilghman Island Retreat By Knapps Narrows!

Tilghman Island Retreat By Knapps Narrows! is a cottage in Tilghman Island, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,188.

From$256/night
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Tilghman Island Retreat By Knapps Narrows! - Tilghman Island, MD

Tilghman Island Retreat By Knapps Narrows!

Holiday Home, Tilghman Island

Tilghman Island Retreat By Knapps Narrows! is a holiday home in Tilghman Island, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Tilghman Island Retreat By Knapps Narrows!

Tilghman Island Retreat By Knapps Narrows! is a holiday home in Tilghman Island, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,841.

From$263/night
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Perfect Waterview Cottage - St. Michaels Getaway - Tilghman Island, MD

Perfect Waterview Cottage - St. Michaels Getaway

Cottage, Tilghman Island

Perfect Waterview Cottage - St. Michaels Getaway is a cottage in Tilghman Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Perfect Waterview Cottage - St. Michaels Getaway

Perfect Waterview Cottage - St. Michaels Getaway is a cottage in Tilghman Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,876.

From$268/night
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Cottage #4 Chesapeake Blue down the drive way. - Tilghman Island, MD

Cottage #4 Chesapeake Blue down the drive way.

Cottage, Tilghman Island

Cottage #4 Chesapeake Blue down the drive way. is a cottage in Tilghman Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cottage #4 Chesapeake Blue down the drive way.

Cottage #4 Chesapeake Blue down the drive way. is a cottage in Tilghman Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,896.

From$271/night
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Browse Waterfront Vacation Rentals in Tilghman Island, MD

Discover vacation rentals close to the coast, water, and beach areas around Tilghman Island, MD.

Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Tilghman Island, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Tilghman Island

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Tilghman Island, with easy beach access, parking, and a quieter setting. This stay gives travelers a comfortable base…

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About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Tilghman Island, with easy beach access, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,720.

From$155/night
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Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Tilghman Island, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Tilghman Island

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Tilghman Island, with easy beach access, kitchen access, and a quieter setting. This stay gives travelers a…

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About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Tilghman Island, with easy beach access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,569.

From$224/night
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Walking distance to Herrington on the Bay! Home with views of the Chesapeake Bay - Tilghman Island, MD

Walking distance to Herrington on the Bay! Home with views of the Chesapeake Bay

Holiday Home, Tilghman Island

Walking distance to Herrington on the Bay! Home with views of the Chesapeake Bay is a holiday home in Tilghman Island, with pet-friendly space, easy beach access, and parking. This stay…

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About Walking distance to Herrington on the Bay! Home with views of the Chesapeake Bay

Walking distance to Herrington on the Bay! Home with views of the Chesapeake Bay is a holiday home in Tilghman Island, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,857.

From$408/night
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Wades Point Inn on the Bay - Tilghman Island, MD

Wades Point Inn on the Bay

B & B, Tilghman Island

Wades Point Inn on the Bay is a b & b in Tilghman Island, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Wades Point Inn on the Bay

Wades Point Inn on the Bay is a b & b in Tilghman Island, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free breakfast, free wifi, parking, paid parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,297.

From$298/night
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Browse Vacation Rentals with a Pool in Tilghman Island, MD

Add a pool to the search when you want an easy place to cool off between outings.

Grandview- Main House - Tilghman Island, MD

Grandview- Main House

Holiday Home, Tilghman Island

Grandview- Main House is a holiday home in Tilghman Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Grandview- Main House

Grandview- Main House is a holiday home in Tilghman Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,543.

From$649/night
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Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly - Tilghman Island, MD

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Holiday Home, Tilghman Island

Minutes from Downtown St. Michaels · Private Dock · Kayaks Bikes · Pet Friendly is a holiday home in Tilghman Island, with pet-friendly space and pool access. This stay gives travelers a…

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About Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Minutes from Downtown St. Michaels · Private Dock · Kayaks Bikes · Pet Friendly is a holiday home in Tilghman Island, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,050.

From$721/night
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Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock - Tilghman Island, MD

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

Cottage, Tilghman Island

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock is a cottage in Tilghman Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock is a cottage in Tilghman Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, ac, air conditioning, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,853.

From$836/night
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Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock - Tilghman Island, MD

Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

Holiday Home, Tilghman Island

Minutes from Downtown St. Michaels · Pool · Hot Tub · Private Dock is a holiday home in Tilghman Island, with pet-friendly space and pool access. This stay gives travelers a comfortable…

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About Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

Minutes from Downtown St. Michaels · Pool · Hot Tub · Private Dock is a holiday home in Tilghman Island, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,430.

From$919/night
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Best Tilghman Island, MD vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Guest Quarters at the Inn - 101 - Tilghman Island, MD

Guest Quarters at the Inn - 101

Apartment, Tilghman Island

Guest Quarters at the Inn - 101 is a apartment in Tilghman Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Guest Quarters at the Inn - 101

Guest Quarters at the Inn - 101 is a apartment in Tilghman Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,390.

From$199/night
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Guest Quarters at the Inn - 102 - Tilghman Island, MD

Guest Quarters at the Inn - 102

Apartment, Tilghman Island

Guest Quarters at the Inn - 102 is a apartment in Tilghman Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Guest Quarters at the Inn - 102

Guest Quarters at the Inn - 102 is a apartment in Tilghman Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,390.

From$199/night
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Guest Quarters at the Inn - 103 - Tilghman Island, MD

Guest Quarters at the Inn - 103

Apartment, Tilghman Island

Guest Quarters at the Inn - 103 is a apartment in Tilghman Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Guest Quarters at the Inn - 103

Guest Quarters at the Inn - 103 is a apartment in Tilghman Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,390.

From$199/night
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Guest quarters at the inn - 204 - Tilghman Island, MD

Guest quarters at the inn - 204

Apartment, Tilghman Island

Guest quarters at the inn - 204 is a apartment in Tilghman Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Guest quarters at the inn - 204

Guest quarters at the inn - 204 is a apartment in Tilghman Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,714.

From$245/night
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Best Pet-Friendly Vacation Rentals in Tilghman Island, MD

Bring your pet along with stays that welcome four-legged travelers.

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis - Tilghman Island, MD

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Apartment, Tilghman Island

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis is a apartment in Tilghman Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis is a apartment in Tilghman Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,328.

From$190/night
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Updated North Beach Cottage: Pet Friendly! - Tilghman Island, MD

Updated North Beach Cottage: Pet Friendly!

Cottage, Tilghman Island

Updated North Beach Cottage: Pet Friendly! is a cottage in Tilghman Island, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Updated North Beach Cottage: Pet Friendly!

Updated North Beach Cottage: Pet Friendly! is a cottage in Tilghman Island, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,660.

From$237/night
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Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly) - Tilghman Island, MD

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cottage, Tilghman Island

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly) is a cottage in Tilghman Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly) is a cottage in Tilghman Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,465.

From$352/night
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Minutes from Downtown St. Michaels | Character Filled - Tilghman Island, MD

Minutes from Downtown St. Michaels | Character Filled

Holiday Home, Tilghman Island

Minutes from Downtown St. Michaels · Character Filled is a holiday home in Tilghman Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Minutes from Downtown St. Michaels | Character Filled

Minutes from Downtown St. Michaels · Character Filled is a holiday home in Tilghman Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,614.

From$373/night
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Best Tilghman Island, MD vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula - Tilghman Island, MD

The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula

Cottage, Tilghman Island

The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula is a cottage in Tilghman Island, with easy beach access, parking, and kitchen access. This stay gives…

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About The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula

The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula is a cottage in Tilghman Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,136.

From$305/night
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Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6 - Tilghman Island, MD

Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6

Holiday Home, Tilghman Island

Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6 is a holiday home in Tilghman Island, with parking, kitchen access, and room for a group. This stay gives…

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About Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6

Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6 is a holiday home in Tilghman Island, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,486.

From$355/night
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Cottage #8 Herons Nest Lg 2 rooms Under Main House - Tilghman Island, MD

Cottage #8 Herons Nest Lg 2 rooms Under Main House

Cottage, Tilghman Island

Cottage #8 Herons Nest Lg 2 rooms Under Main House is a cottage in Tilghman Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cottage #8 Herons Nest Lg 2 rooms Under Main House

Cottage #8 Herons Nest Lg 2 rooms Under Main House is a cottage in Tilghman Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,509.

From$358/night
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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining - Tilghman Island, MD

Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining

Holiday Home, Tilghman Island

Minutes from Downtown St. Michaels and Tilghman · Private Dock · Outdoor Dining is a holiday home in Tilghman Island, with parking and kitchen access. This stay gives travelers a…

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About Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining

Minutes from Downtown St. Michaels and Tilghman · Private Dock · Outdoor Dining is a holiday home in Tilghman Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,746.

From$535/night
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