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Rock Hall Vacation Rentals

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    Waterfront Cottage at Spring Cove1 / 15
    (2)Very good
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Captain's Quarters, a waterfront  couples retreat1 / 12
    (1)Excellent
    Rock Hall
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    * 3 Bedroom Rental House in Historic Rock Hall MD1 / 17
    (3)Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Rock Hall, Maryland 21661
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Rock Hall
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
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    Rock Hall, Maryland 21661
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Rock Hall
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Rock Hall, Maryland 21661
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Rock Hall, Maryland 21661
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Rock Hall
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Rock Hall, Maryland 21661
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Rock Hall, Maryland 21661
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Rock Hall, Maryland 21661
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Rock Hall
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    Pet friendly
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    Rock Hall, Maryland 21661
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Rock Hall
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Rock Hall, Maryland 21661
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Rock Hall
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Grill
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    Pet friendly
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    Smoking allowed
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    Rock Hall, Maryland 21661
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Rock Hall
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
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    Rock Hall, Maryland 21661
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Rock Hall
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Satellite TV
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    • Grill
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Rock Hall, Maryland 21661
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Rock Hall
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Rock Hall, Maryland 21661
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Rock Hall
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
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    Rock Hall, Maryland 21661
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Rock Hall
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Rock Hall, Maryland 21661
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Rock Hall
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Rock Hall, Maryland 21661
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The following rentals are within 15 miles of Rock Hall.
    Chester River House with Views1 / 11
    (2)Very good
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Pet friendly
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    Reviewed August 15, 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...
    Reviewed August 29, 2014
    what a beautiful area of md. to stay at for an relaxing get away.the beautiful sun sets and sunrise.
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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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Bayview by Chesapeake Bay1 / 28
    (3)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Porch
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Private Yard
    • Patio
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 8, 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...
    Reviewed June 10, 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...
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    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...
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    Chestertown, Maryland 21620
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    • Waterfront
    • Air Conditioning
    • Grill
    • DVD Player
    • Washer
    • Patio
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 17, 2014
    If the unit is under construction, do not rent it. We should have been notified of the construction and given the opportunity to cancel.
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    About this property
    Located close to both Chestertown (15 minutes) and Rock Hall (30 minutes), MD this quiet, simple but energetic space is an ideal gathering place for families and friends. Stay here and relax the entire visit or explore the many activities, restaurants and cultural venues available in the Kent...
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    Chestertown, Maryland 21620
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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 Yard
    • Wi-Fi
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 24, 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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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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    • Terrace
    • Balcony
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 6, 2017
    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...
    Reviewed August 27, 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...
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    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...
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    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Stevensville
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave...
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    Stevensville, Kent Island 21666
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Stevensville
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Ocean Views
    • Patio
    • Balcony
    • Washer
    • Central Heating
    • Terrace
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave...
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    Stevensville, Kent Island 21666
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Impressive 3BR Stevensville House Overlooking Eastern Shore w/Wifi, Private Swimming Pool & Game Room - Minutes From the Beach, Golfing & More!1 / 26
    (1)Excellent
    Stevensville
    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 10, 2016
    From the moment you ride up the driveway you already know you are in for a wonderful experience. From the cathedral ceilings to the beautiful decor this home welcomes you. The...
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    About this property
    Have the ultimate Maryland getaway by staying at this remarkable Stevensville vacation rental home, surrounded by approximately 20 breathtaking acres of open space with picturesque Eastern Shore views. Whether you're in the mood for a relaxing escape in the great outdoors or a vacation filled with...
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    Location Information
    Stevensville, Kent Island 21666
    Rental Home - 3 Bedrooms, 5 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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    • Parking
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    Pet friendly
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    Smoking allowed
    Reviewed May 6, 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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    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cape Saint Claire
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Satellite TV
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    located in a safe residential neighborhood with free parking. We are close to shopping, restaurants and the Chesapeake Bay; just minutes drive to the naval academy and downtown Annapolis. Our space is super clean, super spacious, and super comfortable! We are committed to providing you a great...
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    Cape Saint Claire, Maryland 21409
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Stevensville
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Patio
    • Waterfront
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re searching for the perfect place for a family retreat in Stevensville, look no further than this 5-bedroom, 2-bathroom vacation rental house which sleeps 12 in scenic Kent Island. Situated on the shores of Chesapeake Bay, this spacious home boasts 2,600 square feet, plenty of outdoor space...
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    Location Information
    Stevensville, Kent Island 21666
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Stevensville
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Waterfront
    • Balcony
    • Housekeeping Included
    • Ocean Views
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to our private luxury waterfront property that sits on 17 acres located on the Chester River where it meets the mouth of the Chesapeake Bay on Maryland's Eastern Shore. Get away from the city and enjoy the scenic view while having fun on the water. Love Point Bay Luxury Waterfront is at the...
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    Location Information
    Stevensville, Kent Island 21666
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Gorgeous Home on Chester River1 / 16
    (1)Excellent
    Chestertown
    4 Bedrooms, 9 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 7, 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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    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...
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    Chestertown, Maryland 21620
    Rental Home - 4 Bedrooms, 9 Bathrooms, Sleeps 8
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    Blue Goose Cottage1 / 11
    (11)Very good
    Edgemere
    Studio, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 10, 2014
    We got to the cabin on a sat. And it was ready. We were really excited to get away from everything amd when you go there its peace and quite. The kids loved being able to play...
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    About this property
    The most central location for activities in the Deep Creek and Laurel Highlands area. Less than 20 minutes to Casino fun at Nemacolin, PA. Over 60 private acres to explore and enjoy. SNOW MOBILES and FOUR-WHEELERS welcome The best area fishing is within 10 minutes: Bear Creek, Yough river, and the...
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    Location Information
    Edgemere, Maryland 21531
    Rental Home - 1 Bathroom, Sleeps 5
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    Animal Crossing1 / 14
    (16)Average
    Edgemere
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Grill
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lake Access with beautiful BEACH. DOCK SLIP available for a nominal fee less than a five minute drive away (make your rez for slip in advance of your arrival!). Sportsman's Feel with several furs decorating the house and abundant wildlife in yard. Main level offers large screen TV in living room -...
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    Edgemere, Maryland 21561
    Rental Home - 3 Bathrooms, Sleeps 8
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    Waterfront House, Eastern Shore Chesapeake Bay1 / 34
    (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 Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We welcome your inquiries and would be glad to answer any questions you have before booking. In response to inquiries and booking requests, we will send you our standard rental agreement for your information and approval. This house is on the estate of John Raskob, builder of the Empire State...
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    Centreville, Maryland 21617
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)1 / 21
    (3)Excellent
    Chester
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Patio
    • Satellite TV
    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 6, 2016
    We have stayed in this home several times and will return in July. It is a wonderful house with a private master suite at one end, two bedrooms with a 2nd bath at the other.The...
    Reviewed July 29, 2013
    First I would like to say thanks, to Harry, and Scott. They were the best host, I've encountered. They have a property, they can be proud of. The house was just excellent...
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    About this property
    Waterfront Rancher on 3 acres, centrally located between Washington DC, St. Michaels, Annapolis, and Baltimore. 4 Bed/2 Bath home with central air sleeps 8. This home has been in our family for over 50 years and is a special place. Over the years there have been many updates to the home. The...
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    Location Information
    Chester, Kent Island 21619
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxury vacation condominum with private beach1 / 35
    (13)Excellent
    Chester
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Waterfront
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Secure Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 11, 2016
    My family used this home for 10 days over Christmas and New Year. It was just perfect. Plenty of room for our Christmas tree, decorations and packages. Spotlessly clean bedrooms...
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    About this property
    Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 ½ bathrooms, one large family room with open kitchen, one large sunny living room and dinning area. There are 2 king size bed, 2 queen...
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    Location Information
    Chester, Kent Island 21619
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Inquiry
    Rock Hall Flight and Weather Info
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