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Rock Hall Vacation Rentals

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    Don't let other travelers get your favorite Rock Hall area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 25 Rentals in Rock Hall
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    Summer House1 / 10
    (1)Excellent
    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Sailors Crossing1 / 12
    (3)Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Rock Hall
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    The following rentals are within 15 miles of Rock Hall.
    Waterfront House, Eastern Shore Chesapeake Bay1 / 34
    (22)Excellent
    Centreville
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    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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    Cozy & Spacious Chestertown Home1 / 28
    (5)Excellent
    Chestertown
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Patio
    • Private Outdoor Pool (Unheated)
    • Private Yard
    • Wi-Fi
    • DVD Player
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    The pool was 100%. Chemicals were right, but filter was clogged with dead snake, dead frog, flowers an bugs. I arrived before my female companions so cleaned pool. A/c in...
    Reviewed July 4, 2018
    Perfect house for our group of friends. Tons of room and very comfortable. Great area to visit in general. We really enjoyed our visit
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    About this property
    Perfect getaway for friends or families,lovely home in a quiet setting large private salt pool, 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...
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    Chestertown, Maryland 21620
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cape Saint Claire
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Private Yard
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    • Secure Parking
    Suitability
    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, 2 Bathrooms, Sleeps 9
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    Centreville
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
    • Air Conditioning
    • Private Yard
    • Washer
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning upscale private apartment that sleeps 3. Located in a private setting at Wye Branch Manor. Less than 10 miles to golf, outlet shopping, hiking trails and the Wye River. 15 miles to historic Easton, 20 minutes to Saint Michael's and Oxford. The apartment is 1 mile from Wye Mills, there is a...
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    Centreville, Maryland 21671
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-121 / 30
    (1)Excellent
    Chester
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    We had an amazing time at Rosa's house. Her residence is just luxury with modern and lots of class all over. Many pieces from all over the country compliments her design...
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    About this property
    Located in Cox Creek Acres, this detached vacation home and is 30 miles from Baltimore. It provides free private parking. With a large swimming pool, pool towels, outdoor dining area for 8 and much more. There is a seating area, a dining area and a kitchen equipped with dishwasher. A flat-screen TV...
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    Chester, Kent Island 21619
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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
    • Cable/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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    Chester, Kent Island 21619
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Stevensville
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Patio
    • Ocean Views
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Picture yourself sipping morning coffee on the deck watching the charter boats get ready for the big stripers, as the dawn breaks over another perfect day. A modern day home with expansive Captains Quarters and Master Bath overlooking the Chesapeake Bay perfect for the fisherman yet classy enough...
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    Location Information
    Stevensville, Kent Island 21666
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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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
    • Cable/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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    Luxury vacation condominum with private beach1 / 35
    (15)Excellent
    Chester
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 5, 2018
    This condo is spectacular very clean great location on the water. Convenient to restaurants, bike walk trails and outlets! Best decision we ever made to rent this condo...
    Reviewed November 6, 2017
    A great family-friendly condo with a lovely porch view and access to the bay. Our stay was for a wedding at the Chesapeake Beach Bay Club and this location was great. Ying, the...
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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
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    Stevensville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Patio
    • Wi-Fi
    • Private Yard
    • Grill
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located across the bay from Annapolis (just 1.5 miles from the bridge), this is a convenient, quiet, and beautiful alternative to a hotel. Near to the Chesapeake Bay Beach Club, shopping, parks and Matapeake/Terrapin Beaches. Convenient to Annapolis, Baltimore, DC, Easton and St. Michaels....
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    Location Information
    Stevensville, Kent Island 21666
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Chester River House with Views1 / 11
    (4)Very good
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 30, 2018
    With the Chester River in view from the rear of the house, especially from the spacious family room, this is a great stay all around. The bedrooms are roomy, and the beds are...
    Reviewed September 13, 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...
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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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    Gorgeous Home on Chester River1 / 16
    (2)Very good
    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 February 13, 2018
    This is a lovely , comfortable home. We enjoyed our stay very much and would definitely rent the house again. There were a few glitches due to the house having been closed up...
    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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    Belle Rose Cottage at Victory Farm (Pet Friendly!)1 / 17
    (3)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
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    • Private Yard
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 13, 2018
    This is not my first stay at the cottage and I was stoked to be there. My wife and I had more than the space we needed as well as things we needed in the kitchen and laundry in...
    Reviewed January 16, 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...
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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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Stevensville
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Hot Tub
    • Washer
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Space Newly updated features make this property relaxing and highly desirable! Breathtaking views of the Chester River where it meets the mouth of the Chesapeake Bay on Maryland's Eastern Shore. Beautiful cathedral ceilings with a stone stacked fireplace. This is an entertainers delight or a...
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    Stevensville, Kent Island 21666
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Location Information
    Stevensville, Kent Island 21666
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    • Air Conditioning
    • Grill
    • Parking
    • Outdoor Dining Area
    • Private Yard
    • Wi-Fi
    • Washer
    • Cable/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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    Location Information
    Chestertown, Maryland 21620
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Cozy Apartment in Chestertown1 / 7
    (1)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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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    Location Information
    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
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    • Cable/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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    Location Information
    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Chester
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Grill
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy all that Kent island has to offer--golfing, fishing, crabbing and the laid back island life!! Beautifully remodeled 4 Bedroom house in a great community close to Rt 50 and mins from the Bay Bridge!! Whether you are on Maryland's picturesque Eastern shore for its beaches & water activities...
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    Location Information
    Chester, Kent Island 21619
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Stevensville
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Air Conditioning
    • 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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    Huge Stevensville House Overlooking Eastern Shore!1 / 26
    (1)Excellent
    Stevensville
    3 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    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 10
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    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Central Heating
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cottage On Kent is a guest cottage within walking distance to downtown, the Chester River and Washington College. It has one bedroom with a queen size bed, a full kitchen, a spacious bathroom, a cozy living room, off-street parking and access to an outside sitting area. The Cottage is...
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    Location Information
    Chestertown, Maryland 21620
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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