Vacation rentals in Saint Michaels, MD

58 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Saint Michaels, MD

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

Tilghman Island Retreat By Knapps Narrows!

Cottage, Saint Michaels

Tilghman Island Retreat By Knapps Narrows! is a cottage in Saint Michaels, 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 Saint Michaels, 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! - Saint Michaels, MD

Tilghman Island Retreat By Knapps Narrows!

Holiday Home, Saint Michaels

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

Perfect Waterview Cottage - St. Michaels Getaway

Cottage, Saint Michaels

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

Cottage #4 Chesapeake Blue down the drive way.

Cottage, Saint Michaels

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

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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 Saint Michaels, 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 Vacation Rentals with a Pool in Saint Michaels, MD

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

Grandview- Main House - Saint Michaels, MD

Grandview- Main House

Holiday Home, Saint Michaels

Grandview- Main House is a holiday home in Saint Michaels, 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 Saint Michaels, 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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Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock - Saint Michaels, MD

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

Cottage, Saint Michaels

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock is a cottage in Saint Michaels, 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 Saint Michaels, 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 - Saint Michaels, MD

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

Holiday Home, Saint Michaels

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

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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 Saint Michaels, 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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Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels - Saint Michaels, MD

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

Holiday Home, Saint Michaels

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

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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 Saint Michaels, 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 $8,166.

From$1,167/night
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Best Saint Michaels, MD vacation rentals with parking

Find vacation rentals that make arriving by car easier.

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

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

Holiday Home, Saint Michaels

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

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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 Saint Michaels, 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 $2,378.

From$340/night
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Eastons Urban Oasis- centrally located townhome in Talbot County - Saint Michaels, MD

Eastons Urban Oasis- centrally located townhome in Talbot County

Holiday Home, Saint Michaels

Eastons Urban Oasis- centrally located townhome in Talbot County is a holiday home in Saint Michaels, 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 Saint Michaels, 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 $2,441.

From$349/night
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Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! - Saint Michaels, MD

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Holiday Home, Saint Michaels

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! is a holiday home in Saint Michaels, 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 Saint Michaels, 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 $2,447.

From$350/night
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Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6 - Saint Michaels, MD

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

Holiday Home, Saint Michaels

Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6 is a holiday home in Saint Michaels, 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 Saint Michaels, 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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Best Pet-Friendly Vacation Rentals in Saint Michaels, 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. - Saint Michaels, MD

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

Holiday Home, Saint Michaels

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

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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 Saint Michaels, 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 $1,838.

From$263/night
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Pet-Friendly Summer Retreat on Tilghman - Saint Michaels, MD

Pet-Friendly Summer Retreat on Tilghman

Holiday Home, Saint Michaels

Pet-Friendly Summer Retreat on Tilghman is a holiday home in Saint Michaels, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Pet-Friendly Summer Retreat on Tilghman

Pet-Friendly Summer Retreat on Tilghman is a holiday home in Saint Michaels, with pet-friendly space, 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: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,914.

From$273/night
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The Farm House at Hunting Creek - Saint Michaels, MD

The Farm House at Hunting Creek

Holiday Home, Saint Michaels

The Farm House at Hunting Creek is a holiday home in Saint Michaels, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About The Farm House at Hunting Creek

The Farm House at Hunting Creek is a holiday home in Saint Michaels, with pet-friendly space. 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,244.

From$463/night
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Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly - Saint Michaels, MD

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

Holiday Home, Saint Michaels

Minutes from Downtown St. Michaels · Private Dock · Kayaks Bikes · Pet Friendly is a holiday home in Saint Michaels, 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 Saint Michaels, 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 $5,046.

From$721/night
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Best Saint Michaels, MD vacation rentals with a kitchen

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

Downtown Oxford | Character Filled - Saint Michaels, MD

Downtown Oxford | Character Filled

Holiday Home, Saint Michaels

Downtown Oxford · Character Filled is a holiday home in Saint Michaels, 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 Saint Michaels, 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 $2,534.

From$362/night
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Downtown Oxford | Outdoor Dining | Character Filled - Saint Michaels, MD

Downtown Oxford | Outdoor Dining | Character Filled

Holiday Home, Saint Michaels

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

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About Downtown Oxford | Outdoor Dining | Character Filled

Downtown Oxford · Outdoor Dining · Character Filled is a holiday home in Saint Michaels, 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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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining - Saint Michaels, MD

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

Holiday Home, Saint Michaels

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

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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 Saint Michaels, 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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Minutes from Downtown St. Michaels | Private Boat Ramp | Dock - Saint Michaels, MD

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

Holiday Home, Saint Michaels

Minutes from Downtown St. Michaels · Private Boat Ramp · Dock is a holiday home in Saint Michaels, 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 Saint Michaels, 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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Our Favorite Family-Friendly Vacation Rentals in Saint Michaels, MD

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

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! - Saint Michaels, MD

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Cottage, Saint Michaels

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

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About Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! is a cottage in Saint Michaels, 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 $2,738.

From$308/night
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Chic 3 BR / 2 BA Cottage Near Chesapeake Bay - Saint Michaels, MD

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay

Holiday Home, Saint Michaels

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

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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 Saint Michaels, 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 - Saint Michaels, MD

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

Holiday Home, Saint Michaels

Cozy 2-Bedroom Cottage on Tilghman Island – Near Restaurants & Water Activities is a holiday home in Saint Michaels, 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 Saint Michaels, 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 - Saint Michaels, MD

Eastern Shore Waterside Cottage Near St. Michaels

Cottage, Saint Michaels

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

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About Eastern Shore Waterside Cottage Near St. Michaels

Eastern Shore Waterside Cottage Near St. Michaels is a cottage in Saint Michaels, 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 $2,847.

From$407/night
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