Vacation rentals in Sherwood, MD

83 available vacation rental offers

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Best vacation rentals and Airbnb offers in Sherwood, MD

Tilghman Island Retreat By Knapps Narrows! - Sherwood, MD

Tilghman Island Retreat By Knapps Narrows!

Cottage, Sherwood

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

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About Tilghman Island Retreat By Knapps Narrows!

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

Tilghman Island Retreat By Knapps Narrows!

Holiday Home, Sherwood

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

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About Tilghman Island Retreat By Knapps Narrows!

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

Perfect Waterview Cottage - St. Michaels Getaway

Cottage, Sherwood

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

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About Perfect Waterview Cottage - St. Michaels Getaway

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

Cottage #4 Chesapeake Blue down the drive way.

Cottage, Sherwood

Cottage #4 Chesapeake Blue down the drive way. is a cottage in Sherwood, 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 Sherwood, 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 Sherwood, MD

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

Grandview- Main House - Sherwood, MD

Grandview- Main House

Holiday Home, Sherwood

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

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About Grandview- Main House

Grandview- Main House is a holiday home in Sherwood, 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 - Sherwood, MD

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

Holiday Home, Sherwood

Minutes from Downtown St. Michaels · Private Dock · Kayaks Bikes · Pet Friendly is a holiday home in Sherwood, 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 Sherwood, 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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Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock - Sherwood, MD

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

Cottage, Sherwood

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

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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 Sherwood, 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 - Sherwood, MD

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

Holiday Home, Sherwood

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

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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 Sherwood, 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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Vacation rentals with parking in Sherwood, MD

Find vacation rentals that make arriving by car easier.

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

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Sherwood

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

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About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Sherwood, 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 $1,684.

From$150/night
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Relax on Kent Island in a 4 Bedroom Home w/Waterview! - Sherwood, MD

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

Holiday Home, Sherwood

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

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

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

Holiday Home, Sherwood

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

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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 Sherwood, 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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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining - Sherwood, MD

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

Holiday Home, Sherwood

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

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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 Sherwood, 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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Pet-friendly vacation rentals in Sherwood, MD

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

1 Mi to Boardwalk: Convenient North Beach Apt! - Sherwood, MD

1 Mi to Boardwalk: Convenient North Beach Apt!

Apartment, Sherwood

1 Mi to Boardwalk: Convenient North Beach Apt! is a apartment in Sherwood, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About 1 Mi to Boardwalk: Convenient North Beach Apt!

1 Mi to Boardwalk: Convenient North Beach Apt! is a apartment in Sherwood, 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 $1,240.

From$146/night
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Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis - Sherwood, MD

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

Apartment, Sherwood

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis is a apartment in Sherwood, 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 Sherwood, 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 $1,153.

From$165/night
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Minutes from Downtown St. Michaels | Character Filled - Sherwood, MD

Minutes from Downtown St. Michaels | Character Filled

Holiday Home, Sherwood

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

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About Minutes from Downtown St. Michaels | Character Filled

Minutes from Downtown St. Michaels · Character Filled is a holiday home in Sherwood, 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 $2,610.

From$373/night
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Pet-Friendly Tilghman Island Coastal Retreat - Sherwood, MD

Pet-Friendly Tilghman Island Coastal Retreat

Holiday Home, Sherwood

Pet-Friendly Tilghman Island Coastal Retreat is a holiday home in Sherwood, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Pet-Friendly Tilghman Island Coastal Retreat

Pet-Friendly Tilghman Island Coastal Retreat is a holiday home in Sherwood, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,695.

From$385/night
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Vacation rentals with a kitchen in Sherwood, MD

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

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

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Sherwood

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Sherwood, with easy beach access, kitchen access, 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 Sherwood, 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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Chic 3 BR / 2 BA Cottage Near Chesapeake Bay - Sherwood, MD

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay

Holiday Home, Sherwood

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

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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 Sherwood, 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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BOOK NOW FOR SPRING & SUMMER DATES. - Sherwood, MD

BOOK NOW FOR SPRING & SUMMER DATES.

Holiday Home, Sherwood

BOOK NOW FOR SPRING & SUMMER DATES. is a holiday home in Sherwood, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About BOOK NOW FOR SPRING & SUMMER DATES.

BOOK NOW FOR SPRING & SUMMER DATES. is a holiday home in Sherwood, 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: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,520.

From$503/night
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Minutes from Downtown St. Michaels | Private Boat Ramp | Dock - Sherwood, MD

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

Holiday Home, Sherwood

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

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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 Sherwood, 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 Sherwood, MD

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

'callaway Drive Retreat' 3BR Home Near Water - Sherwood, MD

'callaway Drive Retreat' 3BR Home Near Water

Cottage, Sherwood

'callaway Drive Retreat' 3BR Home Near Water is a cottage in Sherwood, with kitchen access, room for a group, and a quieter setting. This stay gives travelers a comfortable base for…

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About 'callaway Drive Retreat' 3BR Home Near Water

'callaway Drive Retreat' 3BR Home Near Water is a cottage in Sherwood, with kitchen access, room for a group, 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 tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,747.

From$184/night
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Updated North Beach Cottage: Pet Friendly! - Sherwood, MD

Updated North Beach Cottage: Pet Friendly!

Holiday Home, Sherwood

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

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About Updated North Beach Cottage: Pet Friendly!

Updated North Beach Cottage: Pet Friendly! is a holiday home in Sherwood, 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,209.

From$225/night
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Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE - Sherwood, MD

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

Cottage, Sherwood

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

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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 Sherwood, 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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Eastern Shore Waterside Cottage Near St. Michaels - Sherwood, MD

Eastern Shore Waterside Cottage Near St. Michaels

Cottage, Sherwood

Eastern Shore Waterside Cottage Near St. Michaels is a cottage in Sherwood, 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 Sherwood, 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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