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Galena Holiday Homes

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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.

    The following rentals are within 40 kilometres of Galena, Maryland.

    1 / 11
    4 of 5 bubbles (2) Very good
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    1 / 14
    4.5 of 5 bubbles (3) Very good
    Chestertown
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 22
    5 of 5 bubbles (1) Excellent
    Chestertown
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 28
    5 of 5 bubbles (3) Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Porch
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Patio
    • Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Quaint, modest one-bedroom cottage near the Chesapeake Bay. Relax and discover the culture, history, nature & cuisine of Maryland's Eastern Shore. Perfect for families, couples and friends. Guests can enjoy great views of the bay and sunsets from the owner's property, which is adjacent to... View all property information
    Location Information
    Chestertown, Maryland 21620
    5 of 5 bubbles Reviewed 9 September 2016
    We have been at this rental for 5 nights now, so thought we would review before we leave the day after tomorrow. The accommodation is set amongst trees near the owners home, with...
    5 of 5 bubbles Reviewed 10 June 2014
    My husband and I were lucky enough to stay in a charming little guest house on the Bay (Tolchester area of Chestertown, MD). House is almost right on the water, very clean, very...
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    1 / 15
    4 of 5 bubbles (2) Very good
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The Cottage takes advantage of its unique environment with a large deck overlooking the extensive lawn and the tranquil waters of Spring Cove. The deck includes a dining set and barbeque grill.The first level includes a screened porch accessed through a first floor bedroom The Cottage is oriented... View all property information
    Location Information
    Rock Hall, Maryland 21661
    4 of 5 bubbles Reviewed 17 September 2014
    My sisters and mother stayed three nights in this quaint house with great views of one of the marina's and cove area. The downstairs was perfect my mother, with a screened in...
    4 of 5 bubbles Reviewed 19 August 2014
    My family was looking for a relaxing getaway that would be an alternative to another week at the beach. We found the perfect spot at this cottage near Rock Hall. We rented with no...
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    1 / 12
    5 of 5 bubbles (1) Excellent
    Rock Hall
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you can enjoy breakfast and... View all property information
    Location Information
    Rock Hall, Maryland 21661
    5 of 5 bubbles Reviewed 2 January 2017
    Lovely, comfortable,clean, friendly with direct access to dock and bay. Lovely views from the many windows. Space is bright and modern while still sortingva large claw foot tube...
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    1 / 34
    5 of 5 bubbles (21) Excellent
    Centreville
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Internet Access
    • Porch
    • Satellite TV
    • Grill
    • Waterfront
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This house is on the estate of John Raskob, builder of the Empire State Building. The four-bedroom, two-bath house is one of seven that Raskob built for his farm employees. Now it has its own dock and swimming pool fronting on Grove Creek, with access to the two-mile-wide Chester River and... View all property information
    Location Information
    Centreville, Maryland 21617
    1 / 7
    5 of 5 bubbles (1) Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Chestertown, Maryland 21620
    5 of 5 bubbles Reviewed 2 weeks ago
    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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    1 / 16
    5 of 5 bubbles (1) Excellent
    Chestertown
    4 Bedrooms, 9 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This gorgeous home is located directly on the Chester River in Chestertown, Md, on the Eastern shore. There are 5 bedrooms, one down and four on the second floor. On the main floor there is a great room that is part kitchen, part TV area and part dining room. Off of this room is a lovely living... View all property information
    Location Information
    Chestertown, Maryland 21620
    5 of 5 bubbles Reviewed 7 June 2016
    Our group - kids and adults - thoroughly enjoyed our stay here. We loved being right on the water and enjoyed the beautiful view. The house was very clean and spacious. It was...
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    1 / 10
    5 of 5 bubbles (7) Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Amenities & Details
    • Terrace
    • Balcony
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An outdoor deck with cafe table and chairs is a nice place to sit on a sunny day. It is perfect for a... View all property information
    Location Information
    Chestertown, Maryland 21620
    5 of 5 bubbles Reviewed 2 weeks ago
    This is a lovely upstairs apartment with a super comfy bed, great shower, and everything you would want or need for an easy stay. The cupboards are stocked, you can cook if you...
    5 of 5 bubbles Reviewed 27 August 2015
    Absolutely the best deal for me in Chestertown. Came back to visit family and friends, and luckily this place was available. Home away from home, roomy, and I was able to work and...
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    1 / 17
    5 of 5 bubbles (3) Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool...
    • Washer
    • Satellite TV
    • Patio
    • DVD Player
    • Porch
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This Spacious Home provides 3 Bedrooms and 2 bathrooms. Each room sleeps 2 people comfortably, and an old fashion cot is provided to sleep one more. This home is completely equipped with all the comforts of home. The Central location is in the heart of the Marina district, steps from Waterman’s... View all property information
    Location Information
    Rock Hall, Maryland 21661
    1 / 6
    4.5 of 5 bubbles (7) Very good
    Delaware City, DE
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Parking
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    LIFE ON THE CANAL IS GOOD! The Delaware City Guest House is a daily / extended stay rental. It is a fully furnished water front rental centrally located between Baltimore and Philadelphia and is close to the Univ. of Delaware, Delaware Park Casino and Dover Downs Casino. Your front deck will be a... View all property information
    Location Information
    Delaware City, Delaware 19706
    5 of 5 bubbles Reviewed 1 October 2015
    I truly hope I get another job in Delaware so I can again stay in this wonderful and charming home. The location was perfect .. with your choice of great restaurants all within...
    5 of 5 bubbles Reviewed 28 August 2015
    The location was the most outstanding feature!! good fishing area and very friendly people (all over). The house was above expectation very clean cozy and featured with all you...
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    1 / 10
    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Grill
    • Parking
    • Porch
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Charming 3 bed / 1 bath single family home with screened in front porch. Relax on the rocking chairs as you take in the charm of this lovely town on one of the prettiest streets in Rock Hall. Ample parking, large back yard with BBQ, tables and chairs to relax with family and friends after spending... View all property information
    Location Information
    Rock Hall, Maryland 21661
    1 / 6
    Elkton
    Private Room, 1 Bathroom, Sleeps 1 | Quick View
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    Amenities & Details
    • Parking
    • Washer
    • Air Conditioning
    • Balcony
    • Grill
    • Waterfront
    • Children's Pool
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    I have a double bed room and a 1 person bedroom with shared bathroom, kitchen, sun room, deck, woods with bonfire, cob oven, yurt, outdoor bathroom, free roaming chickens, cats, dogs, people, plants, gardens, fish pond, playground, bikes available, close to Fair Hill nature preserve, between... View all property information
    Location Information
    Elkton, Maryland 21921
    1 / 6
    Elkton
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
    • Washer
    • Housekeeping...
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Children's Pool
    • Grill
    Suitability
    • Pet-friendly
    • Child-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... View all property information
    Location Information
    Elkton, Maryland 21921