Galena Vacation Rentals
Galena Vacation Rentals
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50 rentals in Galena.
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Life is better at the RIVER!--Cozy waterfront cottage
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
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Be persuaded to experience this vintage cottage by the Sassa
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Riverfront Country House on The Sassafras River
Rental Home
10 bedrooms
6 bathrooms
Sleeps 13
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River Retreat | Private Dock, Deck, Grill, Games & Nature
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Worlds End Chesapeake Cottage
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Eastern Shore Get Away
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
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Beautiful Riverfront Home. With dock, kayaks, paddle board. Magnificent views.
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
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Circa 1900 Home in the Heart of Historic Downtown Chestertown
Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
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BEAUTIFUL BAY FRONT VIEW
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Charming Chestertown Waterfront Cottage
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Lake Home private dock Boating.Eastern shoreChestertown
Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
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350 Acre Waterfront Farm; High Speed Internet, Pool, Sport Court & Private Dock
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
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A European styled retreat on Marylands Eastern Shore with Private pool
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Bonfire by the Creek!!!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
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EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home
Rental Home
6 bedrooms
2 bathrooms
Sleeps 11
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Comfy, Cozy & Perfect!!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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New! Chesapeake Bay house with amazing views
Rental Home
4 bedrooms
3 bathrooms
Sleeps 13
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Bella Vista Holiday Family Gatherings in Coastal Maryland!
Rental Home
5 bedrooms
5 bathrooms
Sleeps 8
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Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Rental Home
6 bedrooms
7 bathrooms
Sleeps 16
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Quiet & Private with Fire Pit Out Back!
Rental Home
3 bedrooms
1 bathroom
Sleeps 7
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5 bedroom Historic Victorian by Chester River
Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
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Enjoy Birdwatching from the Deck!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
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Manor House on Beautiful Eastern Shore Estate
Rental Home
6 bedrooms
5 bathrooms
Sleeps 13
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Private pier and pool at this waterfront Chestertown home
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
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Rambling Victorian Beach House on Maryland's Eastern Shore
Rental Home
8 bedrooms
4 bathrooms
Sleeps 16
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BEACH WITHOUT THE BUSTLE
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Cottage by the Bay
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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NEW! Family-Friendly Cottage, Walk to the Beach!
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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Unobstructed view of the Chesapeake Bay, w/ a beach!
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Uniquely Historic & Quaint Room in the center of downtown Middletown,DE
Condo/Apartment
8 bedrooms
2 bathrooms
Sleeps 8
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Pine Forest Farm
Rental Home
6 bedrooms
3 bathrooms
Sleeps 12
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Come enjoy our luxurious 10,000 sq
Rental Home
7 bedrooms
6 bathrooms
Sleeps 16
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Historic & Quaint Room downtown Middletown, DE awaits you!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Waterfront with Chesapeake Sunsets
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Wren Retweet-Country Estate in the Center of Chestertown
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Carriage House Hideaway in Middle of Chestertown
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Waterfront Views and a Sandy Beach
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Private pier and pool at this waterfront Chestertown home
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
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Private Beach Access, Onsite Kayaks and Shared Boat Ramp
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Amazing 432-Acre Waterfront Estate ~ Dock ~ Kayaks ~ Beaches ~ Fire Pit
Rental Home
11 bedrooms
10 bathrooms
Sleeps 24
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Private Waterfront Estate with Pool, Private Beach and Dock
Rental Home
7 bedrooms
5 bathrooms
Sleeps 18
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The Lazy River House
Rental Home
3 bedrooms
4 bathrooms
Sleeps 12
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Luxury condo with elevator access & free parking
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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WATERFRONT Home * 8000 sq ft * Hot-tub & Pool
Rental Home
4 bedrooms
6 bathrooms
Sleeps 14
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Pine Forest Farm - A Farm Fit for a Princess!
Rental Home
7 bedrooms
3 bathrooms
Sleeps 12
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Overlooking the waters of the Chesapeake Bay
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Showing results 1-50 of 50
Frequently Asked Questions about Galena
- Yes, here are some popular vacation rentals in Galena that have a pool:
- Life is better at the RIVER!--Cozy waterfront cottage
- Be persuaded to experience this vintage cottage by the Sassa
- Riverfront Country House on The Sassafras River
- Yes, here are some popular vacation rentals in Galena that have internet access:
- Life is better at the RIVER!--Cozy waterfront cottage
- Be persuaded to experience this vintage cottage by the Sassa
- Riverfront Country House on The Sassafras River
- Some of the most popular kid friendly rentals in Galena are:
- Life is better at the RIVER!--Cozy waterfront cottage
- Be persuaded to experience this vintage cottage by the Sassa
- Riverfront Country House on The Sassafras River