Vacation rentals in Smith Island, MD

129 available vacation rental offers

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Best vacation rentals and Airbnb offers in Smith Island, MD

Near Chincoteague & Assateague Island Charming 2-bedroom cottage - Smith Island, MD

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Cottage, Smith Island

Near Chincoteague & Assateague Island Charming 2-bedroom cottage is a cottage in Smith Island, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Near Chincoteague & Assateague Island Charming 2-bedroom cottage is a cottage in Smith 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 $992.

From$142/night
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Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville - Smith Island, MD

Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

Holiday Home, Smith Island

Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville is a holiday home in Smith Island, with pet-friendly space, kitchen access, and room for a group. This stay gives…

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About Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville is a holiday home in Smith Island, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,114.

From$159/night
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Pet-friendly Smith Island Cottage w/ Golf Cart! - Smith Island, MD

Pet-friendly Smith Island Cottage w/ Golf Cart!

Cottage, Smith Island

Pet-friendly Smith Island Cottage w/ Golf Cart! is a cottage in Smith Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Pet-friendly Smith Island Cottage w/ Golf Cart!

Pet-friendly Smith Island Cottage w/ Golf Cart! is a cottage in Smith 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 $1,385.

From$161/night
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Pet-Friendly Smith Island Cottage w/ Golf Cart! - Smith Island, MD

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Cottage, Smith Island

Pet-Friendly Smith Island Cottage w/ Golf Cart! is a cottage in Smith Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart! is a cottage in Smith Island, 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 $1,147.

From$164/night
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Waterfront vacation rentals in Smith Island, MD

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

Heathsville Home w/ Sunroom < 10 Mi to Beach! - Smith Island, MD

Heathsville Home w/ Sunroom < 10 Mi to Beach!

Holiday Home, Smith Island

Heathsville Home w/ Sunroom < 10 Mi to Beach! is a holiday home in Smith Island, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Heathsville Home w/ Sunroom < 10 Mi to Beach!

Heathsville Home w/ Sunroom < 10 Mi to Beach! is a holiday home in Smith 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 cancellation, free wifi, beachfront, beach front, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,486.

From$152/night
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Heathsville Home w/ Sunroom < 10 Mi to Beach! - Smith Island, MD

Heathsville Home w/ Sunroom < 10 Mi to Beach!

Holiday Home, Smith Island

Heathsville Home w/ Sunroom < 10 Mi to Beach! is a holiday home in Smith Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Heathsville Home w/ Sunroom < 10 Mi to Beach!

Heathsville Home w/ Sunroom < 10 Mi to Beach! is a holiday home in Smith 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 cancellation, kitchen, with kitchen, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,306.

From$187/night
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Waterfront King Bed Dock SUP Kayak Firepit Porch - for up to 6 - Smith Island, MD

Waterfront King Bed Dock SUP Kayak Firepit Porch - for up to 6

Holiday Home, Smith Island

Waterfront King Bed Dock SUP Kayak Firepit Porch - for up to 6 is a holiday home in Smith Island, with easy beach access and kitchen access. This stay gives travelers a comfortable base for…

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About Waterfront King Bed Dock SUP Kayak Firepit Porch - for up to 6

Waterfront King Bed Dock SUP Kayak Firepit Porch - for up to 6 is a holiday home in Smith Island, with 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,879.

From$268/night
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Potomac River Cottage - Waterfront cottage with endless views! - Smith Island, MD

Potomac River Cottage - Waterfront cottage with endless views!

Cottage, Smith Island

Potomac River Cottage - Waterfront cottage with endless views! is a cottage in Smith Island, with easy beach access and parking. This stay gives travelers a comfortable base for exploring…

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About Potomac River Cottage - Waterfront cottage with endless views!

Potomac River Cottage - Waterfront cottage with endless views! is a cottage in Smith 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 cancellation, free wifi, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,950.

From$279/night
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Vacation rentals with a pool in Smith Island, MD

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

Pool Access! Cozy Couple's Getaway in Kilmarnock - Smith Island, MD

Pool Access! Cozy Couple's Getaway in Kilmarnock

Apartment, Smith Island

Pool Access! Cozy Couple's Getaway in Kilmarnock is a apartment in Smith Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Pool Access! Cozy Couple's Getaway in Kilmarnock

Pool Access! Cozy Couple's Getaway in Kilmarnock is a apartment in Smith Island, 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 $1,095.

From$156/night
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Pool Access! Cozy Couple's Getaway in Kilmarnock - Smith Island, MD

Pool Access! Cozy Couple's Getaway in Kilmarnock

Apartment, Smith Island

Pool Access! Cozy Couple's Getaway in Kilmarnock is a apartment in Smith Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Pool Access! Cozy Couple's Getaway in Kilmarnock

Pool Access! Cozy Couple's Getaway in Kilmarnock is a apartment in Smith 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 $1,322.

From$167/night
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Hosta Cottage | Creekfront Nature Escape w/ Kayaks, Fire Pit + Resort Access, Pet Friendly - Smith Island, MD

Hosta Cottage | Creekfront Nature Escape w/ Kayaks, Fire Pit + Resort Access, Pet Friendly

Cottage, Smith Island

Hosta Cottage · Creekfront Nature Escape w/ Kayaks, Fire Pit + Resort Access, Pet Friendly is a cottage in Smith Island, with pet-friendly space, pool access, and kitchen access. This stay…

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About Hosta Cottage | Creekfront Nature Escape w/ Kayaks, Fire Pit + Resort Access, Pet Friendly

Hosta Cottage · Creekfront Nature Escape w/ Kayaks, Fire Pit + Resort Access, Pet Friendly is a cottage in Smith Island, with pet-friendly space, 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: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,335.

From$191/night
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Year Round Playground - Rare Rustic-Modern Getaway - Smith Island, MD

Year Round Playground - Rare Rustic-Modern Getaway

Cottage, Smith Island

Year Round Playground - Rare Rustic-Modern Getaway is a cottage in Smith Island, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Year Round Playground - Rare Rustic-Modern Getaway

Year Round Playground - Rare Rustic-Modern Getaway is a cottage in Smith Island, with pool 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, pool, hot tub, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,665.

From$524/night
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Vacation rentals with parking in Smith Island, MD

Find vacation rentals that make arriving by car easier.

El Camino - Smith Island, MD

El Camino

Cabin, Smith Island

El Camino is a cabin in Smith Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About El Camino

El Camino is a cabin in Smith 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 $1,019.

From$146/night
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Artistic Environment - Smith Island, MD

Artistic Environment

Holiday Home, Smith Island

Artistic Environment is a holiday home in Smith Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Artistic Environment

Artistic Environment is a holiday home in Smith 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,352.

From$193/night
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Northern Neck Nature Retreat w/ Boat Ramp & Dock! - Smith Island, MD

Northern Neck Nature Retreat w/ Boat Ramp & Dock!

Holiday Home, Smith Island

Northern Neck Nature Retreat w/ Boat Ramp & Dock! is a holiday home in Smith Island, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Northern Neck Nature Retreat w/ Boat Ramp & Dock!

Northern Neck Nature Retreat w/ Boat Ramp & Dock! is a holiday home in Smith 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 $1,530.

From$219/night
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Northern Neck Nature Retreat w/ Boat Ramp & Dock! - Smith Island, MD

Northern Neck Nature Retreat w/ Boat Ramp & Dock!

Cottage, Smith Island

Northern Neck Nature Retreat w/ Boat Ramp & Dock! is a cottage in Smith Island, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Northern Neck Nature Retreat w/ Boat Ramp & Dock!

Northern Neck Nature Retreat w/ Boat Ramp & Dock! is a cottage in Smith 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 $1,795.

From$222/night
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Pet-friendly vacation rentals in Smith Island, MD

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

A Little Serenity - Smith Island, MD

A Little Serenity

Apartment, Smith Island

A Little Serenity is a apartment in Smith Island, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About A Little Serenity

A Little Serenity is a apartment in Smith Island, with pet-friendly space 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 $1,321.

From$151/night
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A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore - Smith Island, MD

A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

Apartment, Smith Island

A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore is a apartment in Smith Island, with pet-friendly space, parking, and kitchen access. This stay gives…

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About A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore is a apartment in Smith Island, 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 $1,215.

From$174/night
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Walk to Beach: Pet-Friendly Gem in Scotland! - Smith Island, MD

Walk to Beach: Pet-Friendly Gem in Scotland!

Cottage, Smith Island

Walk to Beach: Pet-Friendly Gem in Scotland! is a cottage in Smith Island, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Walk to Beach: Pet-Friendly Gem in Scotland!

Walk to Beach: Pet-Friendly Gem in Scotland! is a cottage in Smith 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 $1,431.

From$204/night
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Vacation rentals with a kitchen in Smith Island, MD

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

Awesome private off grid cabin with creek view. - Smith Island, MD

Awesome private off grid cabin with creek view.

Cabin, Smith Island

Awesome private off grid cabin with creek view. is a cabin in Smith Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Awesome private off grid cabin with creek view.

Awesome private off grid cabin with creek view. is a cabin in Smith 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 $1,301.

From$186/night
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ESVA Down by the Sea & Pet Friendly - Smith Island, MD

ESVA Down by the Sea & Pet Friendly

Cottage, Smith Island

ESVA Down by the Sea & Pet Friendly is a cottage in Smith Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About ESVA Down by the Sea & Pet Friendly

ESVA Down by the Sea & Pet Friendly is a cottage in Smith Island, 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 $1,356.

From$194/night
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Dock Access! Family Retreat on the Little Wicomico - Smith Island, MD

Dock Access! Family Retreat on the Little Wicomico

Cottage, Smith Island

Dock Access! Family Retreat on the Little Wicomico is a cottage in Smith Island, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Dock Access! Family Retreat on the Little Wicomico

Dock Access! Family Retreat on the Little Wicomico is a cottage in Smith Island, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,378.

From$273/night
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Dock Access! Family Retreat on the Little Wicomico - Smith Island, MD

Dock Access! Family Retreat on the Little Wicomico

Holiday Home, Smith Island

Dock Access! Family Retreat on the Little Wicomico is a holiday home in Smith Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Dock Access! Family Retreat on the Little Wicomico

Dock Access! Family Retreat on the Little Wicomico is a holiday home in Smith Island, 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 $2,025.

From$289/night
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