Vacation rentals in Galena, MD

26 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Galena, MD

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD - Galena, MD

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Apartment, Galena

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD is a apartment in Galena, with easy beach access and kitchen access. This stay gives travelers a comfortable…

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About WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD is a apartment in Galena, 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, free wifi, kitchen, with kitchen, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,104.

From$120/night
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Eastern Shore Get Away - Galena, MD

Eastern Shore Get Away

Apartment, Galena

Eastern Shore Get Away is a apartment in Galena, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Eastern Shore Get Away

Eastern Shore Get Away is a apartment in Galena, 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 $1,200.

From$143/night
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Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6 - Galena, MD

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Holiday Home, Galena

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6 is a holiday home in Galena, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6 is a holiday home in Galena, 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 $1,253.

From$149/night
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Welcome to Crystal Beach @ the bay. - Galena, MD

Welcome to Crystal Beach @ the bay.

Cottage, Galena

Welcome to Crystal Beach @ the bay. is a cottage in Galena, 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 Welcome to Crystal Beach @ the bay.

Welcome to Crystal Beach @ the bay. is a cottage in Galena, 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 $1,301.

From$151/night
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Best Galena, MD vacation rentals with parking

Find vacation rentals that make arriving by car easier.

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

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

Apartment, Galena

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

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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 Galena, 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 $1,973.

From$232/night
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Newly restored apartment in the heart of Chestertown - Galena, MD

Newly restored apartment in the heart of Chestertown

Apartment, Galena

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

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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 Galena, 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 $2,236.

From$246/night
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Circa 1900 Home in the Heart of Historic Downtown Chestertown - Galena, MD

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Holiday Home, Galena

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

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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 Galena, 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 $2,346.

From$261/night
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Riverside at Pear Tree Point--Waterfront Escape - Galena, MD

Riverside at Pear Tree Point--Waterfront Escape

Holiday Home, Galena

Riverside at Pear Tree Point--Waterfront Escape is a holiday home in Galena, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Riverside at Pear Tree Point--Waterfront Escape

Riverside at Pear Tree Point--Waterfront Escape is a holiday home in Galena, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,963.

From$322/night
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Best Pet-Friendly Vacation Rentals in Galena, MD

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

Miller-Dunham House B&B - Galena, MD

Miller-Dunham House B&B

B & B, Galena

Miller-Dunham House B&B is a b & b in Galena, 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 Miller-Dunham House B&B

Miller-Dunham House B&B is a b & b in Galena, 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 breakfast, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,810.

From$239/night
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EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home - Galena, MD

EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home

Holiday Home, Galena

EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home is a holiday home in Galena, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home

EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home is a holiday home in Galena, 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 $2,773.

From$320/night
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Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town - Galena, MD

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Holiday Home, Galena

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town is a holiday home in Galena, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers…

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About Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town is a holiday home in Galena, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,087.

From$428/night
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Historic Manor House on Beautiful Eastern Shore Estate - Galena, MD

Historic Manor House on Beautiful Eastern Shore Estate

Holiday Home, Galena

Historic Manor House on Beautiful Eastern Shore Estate is a holiday home in Galena, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the…

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About Historic Manor House on Beautiful Eastern Shore Estate

Historic Manor House on Beautiful Eastern Shore Estate is a holiday home in Galena, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $10,180.

From$1,100/night
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Best Galena, MD vacation rentals with a kitchen

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

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown - Galena, MD

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

Holiday Home, Galena

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown is a holiday home in Galena, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown is a holiday home in Galena, 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 $3,269.

From$360/night
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Harbor View Haven | Waterfront w/ Hot Tub + Dock! - Galena, MD

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

Holiday Home, Galena

Harbor View Haven · Waterfront w/ Hot Tub + Dock! is a holiday home in Galena, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Harbor View Haven | Waterfront w/ Hot Tub + Dock!

Harbor View Haven · Waterfront w/ Hot Tub + Dock! is a holiday home in Galena, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,829.

From$396/night
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Victorian Hideaway: Beautiful Exterior, Modern interior - Galena, MD

Victorian Hideaway: Beautiful Exterior, Modern interior

Holiday Home, Galena

Victorian Hideaway: Beautiful Exterior, Modern interior is a holiday home in Galena, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Victorian Hideaway: Beautiful Exterior, Modern interior

Victorian Hideaway: Beautiful Exterior, Modern interior is a holiday home in Galena, 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 $5,641.

From$643/night
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