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Galena Holiday Rentals

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22 rentals in Galena.
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Life is better at the RIVER!--Cozy waterfront cottage, holiday rental in Galena

Life is better at the RIVER!--Cozy waterfront cottage

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Piece of Heaven on the Chesapeake, holiday rental in Galena

Piece of Heaven on the Chesapeake

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Nancy’s Touch, A Waterfront Paradise, holiday rental in Galena

Nancy’s Touch, A Waterfront Paradise

3 bedrooms
2 bathrooms
Sleeps 6
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Chesapeake Bay House on Private Beach, holiday rental in Galena

Chesapeake Bay House on Private Beach

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Riverfront Home. With dock, kayaks, paddle board. Magnificent views., holiday rental in Galena

Beautiful Riverfront Home. With dock, kayaks, paddle board. Magnificent views.

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront house with amazing views Top of the Chesapeake, MD's best kept secret, holiday rental in Galena

Waterfront house with amazing views Top of the Chesapeake, MD's best kept secret

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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This house is a 6 bedroom(s), 6 bathrooms, located in Earleville, MD., holiday rental in Galena

This house is a 6 bedroom(s), 6 bathrooms, located in Earleville, MD.

8 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Waterfront with Chesapeake Sunsets, holiday rental in Galena

Waterfront with Chesapeake Sunsets

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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BEAUTIFUL BAY FRONT VIEW, holiday rental in Galena

BEAUTIFUL BAY FRONT VIEW

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegant waterfront estate on the Upper Chesapeake Bay., holiday rental in Galena

Elegant waterfront estate on the Upper Chesapeake Bay.

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront House, pier, close to Betterton Chestertown & Rockhall, holiday rental in Galena

Waterfront House, pier, close to Betterton Chestertown & Rockhall

4 bedrooms
2 bathrooms
Sleeps 12
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Eastern Shore Getaway: Sleeps 10, Large Yard, Close To Beach, holiday rental in Galena

Eastern Shore Getaway: Sleeps 10, Large Yard, Close To Beach

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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A European styled retreat on Marylands Eastern Shore with Private pool, holiday rental in Galena

A European styled retreat on Marylands Eastern Shore with Private pool

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chestertown's Pet-Friendly Little Red Cottage, holiday rental in Galena

Chestertown's Pet-Friendly Little Red Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Renovated Victorian just a block from the water in historic Havre de Grace, holiday rental in Galena

Renovated Victorian just a block from the water in historic Havre de Grace

3 bedrooms
2 bathrooms
Sleeps 8
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River Lodge, Casual Riverfront setting, holiday rental in Galena

River Lodge, Casual Riverfront setting

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Cozy home with fenced in yard. 2 block walk to historic downtown!, holiday rental in Galena

Cozy home with fenced in yard. 2 block walk to historic downtown!

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Cottage at Broken Spoke Winery, holiday rental in Galena

The Cottage at Broken Spoke Winery

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Clean Bright Trendy Three bed, Two bath Home, holiday rental in Galena

Clean Bright Trendy Three bed, Two bath Home

3 bedrooms
2 bathrooms
Sleeps 7
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Beautiful Waterfront Estate - Special Summer Rates, holiday rental in Galena

Beautiful Waterfront Estate - Special Summer Rates

11 bedrooms
9 bathrooms
Sleeps 27
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Waterfront Sailor's River Cottage, holiday rental in Galena

Waterfront Sailor's River Cottage

2 bedrooms
1 bathroom
Sleeps 6
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Waterfront Views and a Sandy Beach, holiday rental in Galena

Waterfront Views and a Sandy Beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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