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Holiday Rentals and Homes in Wye Mills, MD

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

    Chestertown, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Neavitt
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | 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 / 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
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • ?
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    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 21612
    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 / 9
    5 of 5 stars (1) Excellent
    Bozman
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
    • Patio
    • Waterfront
    • Grill
    • Porch
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Elder access
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    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 21612
    1 / 10
    5 of 5 stars (6) Excellent
    Chestertown, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
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    • Balcony
    • Terrace
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    • Pet-friendly
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    • Child-friendly
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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... View all property information
    Location Information
    Chestertown, Maryland 21620
    5 of 5 stars 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...
    5 of 5 stars Reviewed 12 November 2014
    Would definitely stay again or recommend to friends. Off the beaten path but a stone's throw from everything. Clean, nicely furnished with an eye for the aesthetic. Simple and...
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    1 / 28
    5 of 5 stars (2) Excellent
    Chestertown, MD
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Porch
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Patio
    • Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
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    About this property
    This cozy one-bedroom house is a wonderful spot for a weekend getaway or as a base to discover the culture, history and cuisine of Maryland's Eastern Shore. Enjoy nature, birds - bald eagles, ospreys, blue herons - stunning sunsets and more by the bay. The one-bedroom house includes full kitchen,... View all property information
    Location Information
    Chestertown, Maryland 21620
    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...
    5 of 5 stars Reviewed 9 June 2014
    I stayed at Francesca's lovely Bayview cottage on the Chesapeake Bay in Tolchester, Maryland this weekend. The cottage is delightful, with porches on three sides, comfy beds, and...
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    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
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • 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
    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
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • 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 21673
    5 of 5 stars Reviewed 2 weeks ago
    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 / 11
    4 of 5 stars (2) Very good
    Chestertown, MD
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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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... View all property information
    Location Information
    Chestertown, Maryland 21620
    3 of 5 stars 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...
    5 of 5 stars Reviewed 29 August 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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    Stevensville, MD
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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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... View all property information
    Location Information
    Stevensville, Kent Island 21666
    Rock Hall, MD
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
    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
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    • x
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    • Elder access
    • 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 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 / 12
    4 of 5 stars (2) Very good
    Ridgely, MD
    5 Bedrooms, 5 Bathrooms, Sleeps 13 | Quick View
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    • Grill
    • Porch
    • Satellite TV
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    New bedding in each of the 2 Master Suites, a main level Bedroom, & 2 lower level bedrooms is sure to provide a quality night of rest. Each bedroom offers it's own Flat Screen TV and the Game room downstairs includes a pool & Ping-Pong table 2 separate living areas each offer a quality TV. The... View all property information
    Location Information
    Ridgely, Maryland 21550
    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
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    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 / 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
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • 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 / 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
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    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 21662
    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
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
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    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 21601
    1 / 21
    5 of 5 stars (3) Excellent
    Chester, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
    • Smoking allowed
    • Elder access
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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... View all property information
    Location Information
    Chester, Kent Island 21619
    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 / 40
    3 of 5 stars (5) Average
    Trappe
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Parking
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    • DVD Player
    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    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 21673
    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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    Stevensville, MD
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    About this property
    Large spacious catamaran located on protected cove. NO SAILING EXPERIENCE NECESSARY! Use our catamaran as a large 4 bedroom floating villa. Located on Price creek, this 42' Lagoon cat is the way to spend a vacation on the water. We can also position her in the Annapolis Harbor. Simply take the... View all property information
    Location Information
    Stevensville, Kent Island 21666
    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
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    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 21638
    5 of 5 stars Reviewed 12 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 / 37
    5 of 5 stars (1) Excellent
    Chester, MD
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    • Waterfront
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    • Pet-friendly
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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... View all property information
    Location Information
    Chester, Kent Island 21619
    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
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    • Pet-friendly
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    • x
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    • x
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    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 21663
    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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    1 / 26
    5 of 5 stars (1) Excellent
    Stevensville, MD
    3 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Satellite TV
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    • Waterfront
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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 21666
    5 of 5 stars Reviewed 2 weeks ago
    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 / 21
    5 of 5 stars (1) Excellent
    Chestertown, MD
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Outdoor Dining Area
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    • Wi-Fi
    • Private Garden
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
    • x
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    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 21620
    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 / 20
    5 of 5 stars (1) Excellent
    Easton
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    About this property
    Exclusive 2 bedroom upstairs waterfront apartment with private entrance located 20 minutes from historic Easton and St. Michaels and 30 minutes from Oxford. Enjoy the sunrise each morning on your own private deck overlooking one of the most peaceful and unique surroundings the Eastern Shore has to... View all property information
    Location Information
    Easton, Talbot County 21601
    5 of 5 stars Reviewed 25 July 2015
    This was beyond what I could of hoped for in every way. I actually think the photos on the listing do not do it justice. The property was so tranquil and beautiful. The owner is...
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    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
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    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 21666