Vacation rentals in St. Michaels Winery, MD

54 available vacation rental offers

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Best vacation rentals and Airbnb offers in St. Michaels Winery, MD

Tilghman Island Retreat By Knapps Narrows! - St. Michaels Winery, MD

Tilghman Island Retreat By Knapps Narrows!

Cottage, St. Michaels Winery

Tilghman Island Retreat By Knapps Narrows! is a cottage in St. Michaels Winery, 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 cottage in St. Michaels Winery, 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! - St. Michaels Winery, MD

Tilghman Island Retreat By Knapps Narrows!

Holiday Home, St. Michaels Winery

Tilghman Island Retreat By Knapps Narrows! is a holiday home in St. Michaels Winery, 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 St. Michaels Winery, 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 - St. Michaels Winery, MD

Perfect Waterview Cottage - St. Michaels Getaway

Cottage, St. Michaels Winery

Perfect Waterview Cottage - St. Michaels Getaway is a cottage in St. Michaels Winery, 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 St. Michaels Winery, 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. - St. Michaels Winery, MD

Cottage #4 Chesapeake Blue down the drive way.

Cottage, St. Michaels Winery

Cottage #4 Chesapeake Blue down the drive way. is a cottage in St. Michaels Winery, 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 St. Michaels Winery, 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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Vacation rentals with a pool in St. Michaels Winery, MD

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

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! - St. Michaels Winery, MD

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Holiday Home, St. Michaels Winery

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! is a holiday home in St. Michaels Winery, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! is a holiday home in St. Michaels Winery, with pool 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 cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,445.

From$349/night
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Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock - St. Michaels Winery, MD

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

Holiday Home, St. Michaels Winery

Minutes from Downtown St. Michaels · Pool · Hot Tub · Private Dock is a holiday home in St. Michaels Winery, 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 St. Michaels Winery, 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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Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F - St. Michaels Winery, MD

Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F

Holiday Home, St. Michaels Winery

Minutes from Downtown Easton and St. Michaels · Pool · 1st Floor Bedroom · Pet F is a holiday home in St. Michaels Winery, with pet-friendly space, pool access, and room for a group. This…

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About Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F

Minutes from Downtown Easton and St. Michaels · Pool · 1st Floor Bedroom · Pet F is a holiday home in St. Michaels Winery, with pet-friendly space, pool 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: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,111.

From$1,016/night
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Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels - St. Michaels Winery, MD

Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels

Holiday Home, St. Michaels Winery

Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels is a holiday home in St. Michaels Winery, with pool access and easy beach access. This stay gives travelers a comfortable…

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About Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels

Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels is a holiday home in St. Michaels Winery, with pool access and easy beach 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, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,789.

From$1,113/night
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Vacation rentals with parking in St. Michaels Winery, MD

Find vacation rentals that make arriving by car easier.

Relax on Kent Island in a 4 Bedroom Home w/Waterview! - St. Michaels Winery, MD

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Holiday Home, St. Michaels Winery

Relax on Kent Island in a 4 Bedroom Home w/Waterview! is a holiday home in St. Michaels Winery, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview! is a holiday home in St. Michaels Winery, 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 $2,330.

From$333/night
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Downtown Oxford | Outdoor Dining | Character Filled - St. Michaels Winery, MD

Downtown Oxford | Outdoor Dining | Character Filled

Holiday Home, St. Michaels Winery

Downtown Oxford · Outdoor Dining · Character Filled is a holiday home in St. Michaels Winery, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable…

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About Downtown Oxford | Outdoor Dining | Character Filled

Downtown Oxford · Outdoor Dining · Character Filled is a holiday home in St. Michaels Winery, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,643.

From$378/night
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Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6 - St. Michaels Winery, MD

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

Holiday Home, St. Michaels Winery

Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6 is a holiday home in St. Michaels Winery, 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 St. Michaels Winery, 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 $2,676.

From$382/night
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Downtown Oxford | Outdoor Dining | Character Filled - St. Michaels Winery, MD

Downtown Oxford | Outdoor Dining | Character Filled

Holiday Home, St. Michaels Winery

Downtown Oxford · Outdoor Dining · Character Filled is a holiday home in St. Michaels Winery, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Downtown Oxford | Outdoor Dining | Character Filled

Downtown Oxford · Outdoor Dining · Character Filled is a holiday home in St. Michaels Winery, 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 $3,350.

From$479/night
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Pet-friendly vacation rentals in St. Michaels Winery, MD

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

“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches. - St. Michaels Winery, MD

“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.

Holiday Home, St. Michaels Winery

“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches. is a holiday home in St. Michaels Winery, with easy beach access, parking, and kitchen access. This stay…

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About “It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.

“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches. is a holiday home in St. Michaels Winery, 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,852.

From$265/night
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Downtown Oxford | Character Filled - St. Michaels Winery, MD

Downtown Oxford | Character Filled

Holiday Home, St. Michaels Winery

Downtown Oxford · Character Filled is a holiday home in St. Michaels Winery, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Downtown Oxford | Character Filled

Downtown Oxford · Character Filled is a holiday home in St. Michaels Winery, 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 $2,536.

From$362/night
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Eastons Urban Oasis- centrally located townhome in Talbot County - St. Michaels Winery, MD

Eastons Urban Oasis- centrally located townhome in Talbot County

Holiday Home, St. Michaels Winery

Eastons Urban Oasis- centrally located townhome in Talbot County is a holiday home in St. Michaels Winery, with parking. This stay gives travelers a comfortable base for exploring the area,…

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About Eastons Urban Oasis- centrally located townhome in Talbot County

Eastons Urban Oasis- centrally located townhome in Talbot County is a holiday home in St. Michaels Winery, 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, parking, free parking, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,596.

From$371/night
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Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly - St. Michaels Winery, MD

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

Holiday Home, St. Michaels Winery

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

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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 St. Michaels Winery, 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 $5,068.

From$724/night
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Vacation rentals with a kitchen in St. Michaels Winery, MD

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

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE - St. Michaels Winery, MD

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Cottage, St. Michaels Winery

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE is a cottage in St. Michaels Winery, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE is a cottage in St. Michaels Winery, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,711.

From$387/night
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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining - St. Michaels Winery, MD

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

Holiday Home, St. Michaels Winery

Minutes from Downtown St. Michaels and Tilghman · Private Dock · Outdoor Dining is a holiday home in St. Michaels Winery, 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 St. Michaels Winery, 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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Cottage at Goose Neck Point - St. Michaels Winery, MD

Cottage at Goose Neck Point

Cottage, St. Michaels Winery

Cottage at Goose Neck Point is a cottage in St. Michaels Winery, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cottage at Goose Neck Point

Cottage at Goose Neck Point is a cottage in St. Michaels Winery, 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 $4,032.

From$576/night
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Minutes from Downtown St. Michaels | Private Boat Ramp | Dock - St. Michaels Winery, MD

Minutes from Downtown St. Michaels | Private Boat Ramp | Dock

Holiday Home, St. Michaels Winery

Minutes from Downtown St. Michaels · Private Boat Ramp · Dock is a holiday home in St. Michaels Winery, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Minutes from Downtown St. Michaels | Private Boat Ramp | Dock

Minutes from Downtown St. Michaels · Private Boat Ramp · Dock is a holiday home in St. Michaels Winery, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,245.

From$606/night
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Family-friendly vacation rentals in St. Michaels Winery, MD

Plan a trip with stays that give families more room to spread out.

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! - St. Michaels Winery, MD

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Cottage, St. Michaels Winery

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! is a cottage in St. Michaels Winery, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! is a cottage in St. Michaels Winery, 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 $2,749.

From$309/night
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Chic 3 BR / 2 BA Cottage Near Chesapeake Bay - St. Michaels Winery, MD

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay

Holiday Home, St. Michaels Winery

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay is a holiday home in St. Michaels Winery, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Chic 3 BR / 2 BA Cottage Near Chesapeake Bay

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay is a holiday home in St. Michaels Winery, with easy beach access, 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,420.

From$346/night
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Cozy 2-Bedroom Cottage on Tilghman Island – Near Restaurants & Water Activities - St. Michaels Winery, MD

Cozy 2-Bedroom Cottage on Tilghman Island – Near Restaurants & Water Activities

Holiday Home, St. Michaels Winery

Cozy 2-Bedroom Cottage on Tilghman Island – Near Restaurants & Water Activities is a holiday home in St. Michaels Winery, with parking, kitchen access, and room for a group. This stay gives…

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About Cozy 2-Bedroom Cottage on Tilghman Island – Near Restaurants & Water Activities

Cozy 2-Bedroom Cottage on Tilghman Island – Near Restaurants & Water Activities is a holiday home in St. Michaels Winery, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,480.

From$354/night
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Eastern Shore Waterside Cottage Near St. Michaels - St. Michaels Winery, MD

Eastern Shore Waterside Cottage Near St. Michaels

Cottage, St. Michaels Winery

Eastern Shore Waterside Cottage Near St. Michaels is a cottage in St. Michaels Winery, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Eastern Shore Waterside Cottage Near St. Michaels

Eastern Shore Waterside Cottage Near St. Michaels is a cottage in St. Michaels Winery, 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 $2,985.

From$426/night
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