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Galena Holiday Homes

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    AU$190 Average
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    Don't let other travellers get your favourite Galena area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 15 Rentals in Galena
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    The following rentals are within 30 kilometres of Galena.
    Gorgeous Home on Chester River1 / 16
    (2)Very good
    Chestertown
    4 Bedrooms, 9 Bathrooms, Sleeps 8 Quick View
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    Charming Apartment in Historic Chestertown, MD1 / 10
    (7)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Retreat at a quiet, water front cottage1 / 14
    (3)Very good
    Chestertown
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Chester River House with Views1 / 11
    (3)Very good
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2017
    The house had amazing views right on the river. It was also very comfortable and in a great location close to the little historic square. Would definitely stay here again and...
    Reviewed 15 August 2015
    The sunsets are magnificent. The house is comfy, but showing some deferred maintenance like grass growing from the gutters, green stuff on the exterior, landscaping so very...
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    About this property
    A 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or just visiting a student at...
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    Chestertown, Maryland 21620
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Cozy & Spacious Chestertown Home1 / 25
    (3)Excellent
    Chestertown
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • Private Garden
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 December 2017
    The home was very clean and comfortable. It was very convenient and well set up for 3 generations to stay during our visit to Washington College. Chestertown and Rock Hall...
    Reviewed 21 November 2017
    This property is beautifully appointed. Every amenity possible to make you feel at home. Pool is clean and well maintained. A PLUS!!
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    About this property
    Lovely home in a quiet setting very comfortably furnished all you need for a relaxing getaway. Located 7 miles from the center of Chestertown & 5 miles from the center of Rock Hall. This spacious rancher offers four bedrooms two of the four are master suite's, 3 bathrooms, wood burning fireplace &...
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    Chestertown, Maryland 21620
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Charlestown
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • DVD Player
    • Washer
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Winter sunrises or summer water fun, Waldins is a beautiful retreat any time of year. With the million dollar view just out back there is no need to go anywhere else. State of the art entertainment system and modern kitchen provide all the accoutrements necessary for a comfortable stay. On the...
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    Charlestown, Maryland 21903
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Elkton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Washer
    • Housekeeping Included
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Children's Pool
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have a cozy cute 1 person bedroom and this cozy 2 person bedroom in beautiful wooded setting, close to Fair Hill nature preserve, in Elkton, MD 21921. with shared bathroom, shared kitchen, laundry corner, sun room, pesticide free gardens and eco conscious woods. Short term or long term. Everybody...
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    Elkton, Maryland 21921
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sunview Cottage on Chesapeake Bay1 / 22
    (1)Excellent
    Chestertown
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Parking
    • Outdoor Dining Area
    • Private Garden
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2015
    I took my mother here for a getaway birthday weekend. I wanted somewhere we could relax but also be inspired by our surroundings. This quaint cottage was perfect. Nestled close...
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    About this property
    Modern, Cozy 2-Bedroom Cottage with sleeping loft. Views of the Chesapeake Bay from house and wraparound deck. Perfect destination for a couples getaway, family trip or friends gathering to enjoy the Bay & Sunsets. Located in the scenic, serene environs of the Eastern Shore of Maryland in...
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    Chestertown, Maryland 21620
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Still Pond
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • Washer
    • Terrace
    • Patio
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious room w old pine floors, comes with semi-private bathroom, breakfast and some meals provided, in a charming Victorian in delightful town, half acre lot and shared use of rooms. Out and out close for 15 scenic launching areas for boating. Less than 5 mins to spectacular sunsets at Betterton....
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    Still Pond, Maryland 21667
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Charlestown
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront living at its best. About 40 minutes from downtown Baltimore and 1.5 hours from DC. This is a quiet family oriented area, not a bustling tourist town. Bring your boat and put it in at the nearby ramp. Lovely bamboo floors in the living room. Fantastic views of the Chesapeake Bay. Kayak...
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    Charlestown, Maryland 21903
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Chesapeake City
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This luxurious and recently built villa is ideally positioned, providing sumptuous, dazzling panoramic views over the Pinhal golf course, on the outskirts of Vilamoura. Boasting spacious living areas, the villa is equipped with a state of the art kitchen, as well as four elegant bedrooms all with...
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    Chesapeake City, Maryland 8125 422
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Cozy Apartment in Chestertown1 / 7
    (1)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    This first floor apartment is cozy, sweet, and convenient to everything downtown. A quick 2 block walk brings you to restaurants, shops, galleries, the Farmer's Market on...
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    About this property
    A delightful one-bedroom apartment located in historic Chestertown. Close to Washington College & Heron Point. Apartment accommodates 2 guests. It is the perfect place for enjoying this historic, artistic town on Maryland's Eastern Shore. The space includes kitchen/living room combo, bedroom with...
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    Location Information
    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Belle Rose Cottage at Victory Farm (Pet Friendly!)1 / 17
    (2)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2018
    This cottage is a little piece of heaven. Everything you need for a short- or long-term stay is right at your fingertips: a full-sized kitchen, living room, bedroom, and a...
    Reviewed 17 January 2018
    This cottage just begs you to slow down and relax. Gorgeous sunsets coupled with interesting sights of a real farm make this cottage picture perfect... we found neat shops and...
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    About this property
    Nestled behind the main house with a fenced garden, the cottage is a cozy respite after a busy day site seeing or visiting with local friends. Relax and discover the culture, history, nature, and cuisines of Maryland's Eastern Shore. Perfect for folks traveling with a dog or two. Short or long term...
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    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Still Pond
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Private Garden
    • Washer
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious room w old pine floors, comes with semi-private bathroom, breakfast and some meals provided, in a charming Victorian in delightful town, half acre lot and shared use of rooms. Out and out close for 15 scenic launching areas for boating. Less than 5 mins to spectacular sunsets at Betterton....
    View all property information
    Location Information
    Still Pond, Maryland 21667
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Elkton
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Amenities & Details
    • Secure Parking
    • Washer
    • Air Conditioning
    • Balcony
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have 2 double bed rooms and a 1 person bedroom with shared bathroom, kitchen, sun room, deck, woods with bonfire, cob oven, yurt, outdoor bathroom, free roaming chickens, sheep, goat, cats, dogs, people, plants, gardens, fish pond, playground, bikes available, close to Fair Hill nature preserve,...
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    Location Information
    Elkton, Maryland 21921
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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