Vacation rentals in Smith Island, MD

130 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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Charming studio apartment water front on Cranes Creek Just off Ingram Bay - Smith Island, MD

Charming studio apartment water front on Cranes Creek Just off Ingram Bay

Apartment, Smith Island

Charming studio apartment water front on Cranes Creek Just off Ingram Bay is a apartment in Smith Island, with easy beach access and kitchen access. This stay gives travelers a comfortable…

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About Charming studio apartment water front on Cranes Creek Just off Ingram Bay

Charming studio apartment water front on Cranes Creek Just off Ingram Bay is a apartment 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, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,110.

From$159/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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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 $1,023.

From$146/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 $1,531.

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 $1,796.

From$223/night
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The Whitehaven Hotel - Smith Island, MD

The Whitehaven Hotel

B & B, Smith Island

The Whitehaven Hotel is a b & b in Smith Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About The Whitehaven Hotel

The Whitehaven Hotel is a b & b in Smith Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,265.

From$161/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 $1,346.

From$192/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 $2,380.

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 $2,026.

From$289/night
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