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Vacation Rentals in Wye Mills, MD and nearby

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    The following rentals are within 30 kilometres of Wye Mills, Talbot County, Maryland.

    1 / 10
    5 of 5 stars (6) Excellent
    Chestertown, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 11
    4 of 5 stars (2) Very good
    Chestertown, MD
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    1 / 22
    4.5 of 5 stars (3) Very good
    Chestertown, MD
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 28
    5 of 5 stars (3) Excellent
    Chestertown, MD
    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
    5 of 5 stars Reviewed 3 weeks ago
    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 stars 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
    Chestertown, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • Housekeeping...
    • Satellite TV
    • Balcony
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our Victorian cottage, built in the 1880s and upgraded to more modern standards, offers the best of both worlds: A bit of a rural feel, with a fenced-in side yard and back yard, a lovely porch swing, and ... easy strolling distance to the downtown historic Chestertown. Did you know that the... View all property information
    Location Information
    Chestertown, Maryland
    1 / 21
    5 of 5 stars (1) Excellent
    Chestertown, MD
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Air Conditioning
    • Grill
    • Parking
    • Outdoor Dining Area
    • Private Garden
    • Wi-Fi
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Modern, Cozy 2-Bedroom Cottage with sleeping loft. Views of the Chesapeake Bay from wraparound deck. Perfect destination for families & friends for Bay & Sunsets. Located in the scenic, serene environs of the Eastern Shore of Maryland in Tolchester. The two-bedroom house with sleeping loft... View all property information
    Location Information
    Chestertown, Maryland
    5 of 5 stars Reviewed 24 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 to...
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    1 / 55
    3 of 5 stars (5) Average
    Trappe
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Outdoor Dining Area
    • Air Conditioning
    • Patio
    • Parking
    • Washer
    • Grill
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Beautiful, serene waterfront home on the Chesapeake Bay. One hour from the Atlantic Ocean (Ocean City, Assateague Island) and Annapolis, One and a half hours from Washington DC and Baltimore. Many nearby places worth visiting, including picturesque St. Michaels and the Blackwater Wildlife Refuge... View all property information
    Location Information
    Trappe, Talbot County
    4 of 5 stars Reviewed 23 July 2015
    We had a blast. The property, although the actual house could use a bit of updating, is GORGEOUS. We did notice that the home definitely housed a pet or two but did not smell...
    5 of 5 stars Reviewed 26 August 2014
    Beautiful home and view of the bay. Private beach was amazing. Perfect for a group of friends or a couple looking to get away. I will definitely be staying here again!
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    1 / 16
    5 of 5 stars (1) Excellent
    Chestertown, MD
    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
    • 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
    5 of 5 stars 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 / 12
    Rock Hall, MD
    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
    1 / 15
    4 of 5 stars (2) Very good
    Rock Hall, MD
    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
    4 of 5 stars Reviewed 16 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 stars 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 / 11
    Stevensville, MD
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Stevensville, Kent Island
    1 / 9
    5 of 5 stars (1) Excellent
    Bozman
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Amenities & Details
    • Internet Access
    • Patio
    • Waterfront
    • Grill
    • Porch
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas... View all property information
    Location Information
    Bozman, Talbot County
    1 / 11
    Neavitt
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Patio
    • Wi-Fi
    • Waterfront
    • Washer
    • Grill
    • Parking
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Newly renovated cottage in the village of Neavitt. Neavitt is a great village only 10 minutes away from St. Michaels. The house has waterviews and access to it's own personal dock which is great for fishing, kayaking or paddle boarding. Spend the day out on local waterways and then relax the night... View all property information
    Location Information
    Neavitt, Talbot County
    1 / 29
    5 of 5 stars (1) Excellent
    Trappe
    8 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    • Private Outdoor...
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • Patio
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Martins Point is a late 18th Century house and cottages on Maryland's historic Eastern Shore where the Underground Railroad once passed through the property. It is located on a secluded finger of land, surrounded by water on three sides, a place to unwind, immerse yourself in the natural beauty of... View all property information
    Location Information
    Trappe, Talbot County
    5 of 5 stars Reviewed 13 May 2016
    A group of 11 older adults with Eastern Shore roots was looking for a place to hold a reunion, and luckily we found Martins Point. The property is beautifully kept, with the main...
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    1 / 21
    5 of 5 stars (3) Excellent
    Chester, MD
    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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Chester, Kent Island
    5 of 5 stars Reviewed 6 January 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...
    5 of 5 stars Reviewed 29 July 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. The...
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    1 / 7
    5 of 5 stars (9) Excellent
    Bozman
    4 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    • Satellite TV
    • Grill
    • Internet Access
    • Patio
    • Air Conditioning
    • Porch
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch (2 queens, 1 double, daybed w/trundle, 5 twins) 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large... View all property information
    Location Information
    Bozman, Talbot County
    5 of 5 stars Reviewed 9 June 2015
    Perfectly situated on the water. The views are amazing, as is the pool. There is a huge lawn which is perfect for children of all ages. A short drive to St. Michael's, which is a...
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    1 / 17
    5 of 5 stars (3) Excellent
    Rock Hall, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • 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
    1 / 41
    Trappe
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom... View all property information
    Location Information
    Trappe, Talbot County
    1 / 15
    Easton
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • Satellite TV
    • Wi-Fi
    • Waterfront
    • Ocean Views
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    4+ acres on Shipshead Creek off of St. Michaels road. Fully furnished (2 king and 4 twin beds), heated pool, deep water dock, tennis court,and pet friendly. Boat, Jet Ski, Paddle Board, Kayak, Canoe, and Bike rentals can be arranged-Inquire if interested The Space Pet Friendly waterfront... View all property information
    Location Information
    Easton, Talbot County
    1 / 26
    5 of 5 stars (1) Excellent
    Stevensville, MD
    3 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Private Outdoor...
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Stevensville, Kent Island
    5 of 5 stars Reviewed 10 May 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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    1 / 9
    Rock Hall, MD
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • 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
    1 / 20
    Preston, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Secure Parking
    • DVD Player
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Beautiful 18 acres large deck over looks historical woods. Nature at its best... Hawks, rabbits, deer, all kinds of birds.... Our hummin birds are fabulous... WE have a complimentary canoe, bikes, we can set up a water slide for a fee also manicures and pedicures plus ear candling done on site for... View all property information
    Location Information
    Preston, Maryland
    1 / 16
    Preston, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Secure Parking
    • Shared Indoor Pool
    • Private Garden
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our home has a beautiful fire fly show in our historical wooded back yard. Always enjoy our wildlife our humming birds are the best. Go four leaf clover hunting. The deck is comfortable with lounge chairs for basting in the summer sun. We have goats that get loose... The horse that lives in our... View all property information
    Location Information
    Preston, Maryland
    1 / 34
    Trappe
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom... View all property information
    Location Information
    Trappe, Talbot County
    1 / 18
    Neavitt
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Balcony
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Full renovations just completed on this newly-listed historic waterfront home. Sleeps five (1 King, 1 Queen, 1 Twin). Kick back, relax and enjoy the beautiful waterviews. Have crabs on the deck or cocktails on the dock. Features a new dock with 14 ft. and 16 ft. wide, deepwater boat slips. Bring... View all property information
    Location Information
    Neavitt, Talbot County
    1 / 40
    Trappe
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom... View all property information
    Location Information
    Trappe, Talbot County
    1 / 14
    McDaniel
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Central Heating
    • Patio
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Halo's Haven is a true piece of Heaven!! Bring your boat and your bathing suit. Twenty picturesque acres on a beautiful point of land off of the Chesapeake Bay near historic St. Michael's, Maryland. This property is beautifully landscaped, has a waterfront pool, pool house with bathroom, boat dock... View all property information
    Location Information
    McDaniel, St. Michaels
    1 / 12
    5 of 5 stars (1) Excellent
    Grasonville, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
    • Hot Tub
    • Satellite TV
    • Waterfront
    • Patio
    • Air Conditioning
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to Baydreams vacation home, a unique waterfront vacation home situated near the Kent Narrows in Queen Anne's County, on the Eastern Shore of Maryland. Book the comfort and convenience of a 4 bedroom 3 bath home offering a unique lodging to the discriminating traveler that other... View all property information
    Location Information
    Grasonville, Maryland
    5 of 5 stars Reviewed 11 August 2015
    Baydreams backs onto a Chesapeake Bay inlet. The view from the back windows is beautiful and tranquil. We were particularly impressed with a close view of ospreys nesting behind a...
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    1 / 9
    Royal Oak
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Washer
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Balcony
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    You can tell right away, from the warm sage green exterior and the peaceful creekside setting, that this charming vacation cottage promises a fun, relaxing getaway. With a 180 degree expanse of spectacular Oak Creek waterfront, the River House at Royal Oak is the pefect choice for year 'round... View all property information
    Location Information
    Royal Oak, Talbot County
    1 / 23
    2 of 5 stars (1) Poor
    Stevensville, MD
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Grill
    • Washer
    • Patio
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Beautiful 4 Bedroom, 4 Bath Quiet Waterfront Property, 3 queen bedrooms, 1 twin beds, 4 baths, two stories, fantastic master bedroom with mater bath complete with Roman soaking tub. Deck off of the master bedroom. Formal living room, Family room, Glass Sunroom, eat in kitchen, this spacious comes... View all property information
    Location Information
    Stevensville, Kent Island
    1 / 35
    5 of 5 stars (1) Excellent
    Chester, MD
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • Hot Tub
    • Parking
    • Washer
    • Internet Access
    • Waterfront
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Chester, Kent Island
    5 of 5 stars Reviewed 11 January 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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    1 / 11
    4.5 of 5 stars (2) Very good
    Claiborne
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • Private Outdoor...
    • Internet Access
    • Washer
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes to many quaint watermen villages. Shared waterside pool, beach, kayaks, small boat, childrens playset. The property was designed to take advantage of the incredible views of the Chesapeake... View all property information
    Location Information
    Claiborne, Talbot County
    4 of 5 stars Reviewed 27 June 2015
    We were a group of two couples each with a young child. There was more than enough room for the 6 of us. The home is well located in Claiborne, about 5 min from downtown...
    5 of 5 stars Reviewed 10 October 2014
    Very new, very clean, very spacious, very comfortable. The family thoroughly enjoyed our stay here with plenty of room to spread out, a huge kitchen, meals on the deck and...
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