Vacation rentals in Pooles Island, MD

50 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Pooles Island, MD

Studio apartment in water view Historic home with WiFi, separate AC/heat - Pooles Island, MD

Studio apartment in water view Historic home with WiFi, separate AC/heat

Apartment, Pooles Island

Studio apartment in water view Historic home with WiFi, separate AC/heat is a apartment in Pooles Island, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Studio apartment in water view Historic home with WiFi, separate AC/heat

Studio apartment in water view Historic home with WiFi, separate AC/heat is a apartment in Pooles 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $834.

From$119/night
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The Tolhouse Short or Long-Term - Pooles Island, MD

The Tolhouse Short or Long-Term

Apartment, Pooles Island

The Tolhouse Short or Long-Term is a apartment in Pooles Island. 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 Tolhouse Short or Long-Term

The Tolhouse Short or Long-Term is a apartment in Pooles Island. 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $859.

From$123/night
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3 Mi to Washington College! Updated Home w/ Patio - Pooles Island, MD

3 Mi to Washington College! Updated Home w/ Patio

Cottage, Pooles Island

3 Mi to Washington College! Updated Home w/ Patio is a cottage in Pooles Island, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About 3 Mi to Washington College! Updated Home w/ Patio

3 Mi to Washington College! Updated Home w/ Patio is a cottage in Pooles Island, with outdoor 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,423.

From$135/night
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3 Mi to Washington College! Updated Home w/ Patio - Pooles Island, MD

3 Mi to Washington College! Updated Home w/ Patio

Holiday Home, Pooles Island

3 Mi to Washington College! Updated Home w/ Patio is a holiday home in Pooles Island, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 3 Mi to Washington College! Updated Home w/ Patio

3 Mi to Washington College! Updated Home w/ Patio is a holiday home in Pooles Island, with outdoor 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,214.

From$173/night
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Browse Waterfront Vacation Rentals in Pooles Island, MD

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

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River - Pooles Island, MD

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River

Apartment, Pooles Island

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River is a apartment in Pooles Island, with parking, kitchen access, and room for a group. This stay gives…

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About Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River is a apartment in Pooles 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,861.

From$266/night
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200 steps to the beach! - Pooles Island, MD

200 steps to the beach!

Holiday Home, Pooles Island

200 steps to the beach! is a holiday home in Pooles Island, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area,…

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About 200 steps to the beach!

200 steps to the beach! is a holiday home in Pooles 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 $2,236.

From$319/night
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Bayside Cottage steps from Rock Hall Harbor - Pooles Island, MD

Bayside Cottage steps from Rock Hall Harbor

Holiday Home, Pooles Island

Bayside Cottage steps from Rock Hall Harbor is a holiday home in Pooles Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor is a holiday home in Pooles Island, 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 $2,323.

From$332/night
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Beautiful, spacious, quiet waterfront house! - Pooles Island, MD

Beautiful, spacious, quiet waterfront house!

Holiday Home, Pooles Island

Beautiful, spacious, quiet waterfront house! is a holiday home in Pooles Island, with easy beach access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

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About Beautiful, spacious, quiet waterfront house!

Beautiful, spacious, quiet waterfront house! is a holiday home in Pooles Island, 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: hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,727.

From$390/night
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Browse Vacation Rentals with a Pool in Pooles Island, MD

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

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. - Pooles Island, MD

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.

Holiday Home, Pooles Island

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. is a holiday home in Pooles Island, with pool access, easy beach access, and kitchen access. This stay gives…

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About A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. is a holiday home in Pooles Island, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,223.

From$1,175/night
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Inn at Haven Harbour - Pooles Island, MD

Inn at Haven Harbour

B & B, Pooles Island

Inn at Haven Harbour is a b & b in Pooles Island, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Inn at Haven Harbour

Inn at Haven Harbour is a b & b in Pooles Island, 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: free breakfast, pool, free wifi, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,197.

From$263/night
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Inn at Huntingfield Creek - Pooles Island, MD

Inn at Huntingfield Creek

B & B, Pooles Island

Inn at Huntingfield Creek is a b & b in Pooles Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Inn at Huntingfield Creek

Inn at Huntingfield Creek is a b & b in Pooles 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 breakfast, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,490.

From$320/night
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Best Pooles Island, MD vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Newly restored apartment in the heart of Chestertown - Pooles Island, MD

Newly restored apartment in the heart of Chestertown

Apartment, Pooles Island

Newly restored apartment in the heart of Chestertown is a apartment in Pooles Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown is a apartment in Pooles 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,026.

From$289/night
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Circa 1900 Home in the Heart of Historic Downtown Chestertown - Pooles Island, MD

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Holiday Home, Pooles Island

Circa 1900 Home in the Heart of Historic Downtown Chestertown is a holiday home in Pooles Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Circa 1900 Home in the Heart of Historic Downtown Chestertown

Circa 1900 Home in the Heart of Historic Downtown Chestertown is a holiday home in Pooles 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,213.

From$316/night
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Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall - Pooles Island, MD

Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall

Holiday Home, Pooles Island

Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall is a holiday home in Pooles Island, with parking and room for a group. This stay gives travelers a comfortable base…

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About Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall

Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall is a holiday home in Pooles Island, with parking 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, parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,244.

From$321/night
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Serenity on the Cove - Pooles Island, MD

Serenity on the Cove

Holiday Home, Pooles Island

Serenity on the Cove is a holiday home in Pooles 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 Serenity on the Cove

Serenity on the Cove is a holiday home in Pooles 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 $2,322.

From$332/night
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Best Pet-Friendly Vacation Rentals in Pooles Island, MD

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

Beautiful Retreat Located in Rock Hall - walk to everything! - Pooles Island, MD

Beautiful Retreat Located in Rock Hall - walk to everything!

Holiday Home, Pooles Island

Beautiful Retreat Located in Rock Hall - walk to everything! is a holiday home in Pooles Island, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

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About Beautiful Retreat Located in Rock Hall - walk to everything!

Beautiful Retreat Located in Rock Hall - walk to everything! is a holiday home in Pooles 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 $2,069.

From$296/night
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Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay - Pooles Island, MD

Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay

Holiday Home, Pooles Island

Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay is a holiday home in Pooles Island, with pet-friendly space, easy beach access, and kitchen access. This…

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About Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay

Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay is a holiday home in Pooles Island, 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 $2,088.

From$298/night
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Quiet Bird River Bungalow and Nature Retreat Pet Friendly - Pooles Island, MD

Quiet Bird River Bungalow and Nature Retreat Pet Friendly

Holiday Home, Pooles Island

Quiet Bird River Bungalow and Nature Retreat Pet Friendly is a holiday home in Pooles Island, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a…

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About Quiet Bird River Bungalow and Nature Retreat Pet Friendly

Quiet Bird River Bungalow and Nature Retreat Pet Friendly is a holiday home in Pooles Island, 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: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,138.

From$305/night
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Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD - Pooles Island, MD

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Holiday Home, Pooles Island

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD is a holiday home in Pooles Island, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a…

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About Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD is a holiday home in Pooles Island, with pet-friendly space, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,184.

From$312/night
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Best Pooles Island, MD vacation rentals with a kitchen

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

Serene Waterfront Cottage with dock and gorgeous views. - Pooles Island, MD

Serene Waterfront Cottage with dock and gorgeous views.

Holiday Home, Pooles Island

Serene Waterfront Cottage with dock and gorgeous views. is a holiday home in Pooles Island, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable…

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About Serene Waterfront Cottage with dock and gorgeous views.

Serene Waterfront Cottage with dock and gorgeous views. is a holiday home in Pooles 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 $2,390.

From$341/night
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Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio - Pooles Island, MD

Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio

Holiday Home, Pooles Island

Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio is a holiday home in Pooles Island, with easy beach access, outdoor space, and parking. This stay gives travelers a…

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About Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio

Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio is a holiday home in Pooles Island, with easy beach access, outdoor 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,473.

From$353/night
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Newly renovated single family home with attached guest suite - Pooles Island, MD

Newly renovated single family home with attached guest suite

Holiday Home, Pooles Island

Newly renovated single family home with attached guest suite is a holiday home in Pooles Island, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite is a holiday home in Pooles Island, with 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 $2,675.

From$382/night
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Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore! - Pooles Island, MD

Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore!

Holiday Home, Pooles Island

Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore! is a holiday home in Pooles Island, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore!

Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore! is a holiday home in Pooles 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,998.

From$428/night
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