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Vacation Rentals in Ridgely, MD and nearby

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    26 Vacation Rentals in Ridgely
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    The following rentals are within 40 kilometres of Ridgely, Maryland.

    From
    $110
    / Night
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    Overview Reviews (2)
    From
    $305
    / Night
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    1 / 15
    4 of 5 stars (2) Very good
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (2)
    From
    $305
    / Night
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    Overview Reviews (3)
    From
    $177
    / Night
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    1 / 11
    5 of 5 stars (1) Excellent
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
    Overview Reviews (1)
    From
    $549
    / Night
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    Overview Reviews (5)
    From
    $360
    / Night
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    Overview Reviews (3)
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Fireplace
    • Waterfront
    • Dryer
    • Deck
    • Refrigerator
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    3 of 5 stars Reviewed 18 October 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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    From
    $121
    / Night
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    Overview Reviews (5)
    Amenities & Details
    • TV
    • Internet Access
    • Waterfront
    • Linens Provided
    • Balcony
    • Cooker
    • There Are Tennis...
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An air mattress can be set up in the living room for 2 additional guests. An outdoor deck with cafe... View all property information
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    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...
    5 of 5 stars Reviewed 25 July 2014
    We enjoyed our stay in this very pleasant and bright apartment, walking distance to the visitor's center, the downtown with many shops and restaurants, and the Chester River. The...
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    From
    $146
    / Night
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    1 / 28
    5 of 5 stars (2) Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Overview Reviews (2)
    Amenities & Details
    • Porch
    • Air Conditioning
    • Watersports Nearby
    • Refrigerator
    • Linens Provided
    • Internet Access
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
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    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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    From
    $457
    / Night
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    Overview Reviews (1)
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Internet Access
    • Watersports Nearby
    • Boat Available
    • Shared Outdoor Pool...
    • Water Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sandy Pines, with its own waterfront, dock, and swimming pool, offers a peaceful retreat within the quiet natural beauty of the Chesapeake Bay region. The very private home, sited on broad Harris Creek, enjoys stunning sunset views across the Chesapeake tributary, and is fully-equipped and... View all property information
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    From
    $255
    / Night
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    1 / 11
    Stevensville
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    From
    $134
    / Night
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    Overview
    Amenities & Details
    • Private Fishing...
    • Air Conditioning
    • Stereo System
    • TV
    • DVD Player
    • Wi-Fi
    • There Are Tennis...
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    HOME ON THE RIVER: A view of Choptank River (read James Michener's 'Chesapeake') from all rooms in cozy 2 bedroom apartment with full kitchen & bath. Separate entrance, patio, dock with canoe and kayaks. Peaceful setting within 2 miles of town and relatively close to Washington D.C., Baltimore.&... View all property information
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    From
    $287
    / Night
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    1 / 6
    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
    Overview
    Amenities & Details
    • Grill
    • Patio
    • Parking
    • Linens Provided
    • DVD Player
    • Refrigerator
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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
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    From
    $220
    / Night
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    1 / 12
    Rock Hall
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • 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
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    From
    $305
    / Night
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    Overview
    Amenities & Details
    • Washer
    • Water Views
    • Dryer
    • Waterfront
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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
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    From
    $926
    / Night
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    Overview
    Amenities & Details
    • Private Outdoor...
    • Boat Available
    • Water Views
    • Washer
    • Fireplace
    • Waterfront
    • Satellite TV
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Walk to the attractions of St. Michaels, MD, yet private and quiet on a point of land with 500' shoreline, Bay Cottage is your home on the Chesapeake Bay with a relaxing waterside pol, private harbor and pier, organic culinary gardens, fruit farm, wellness studio, and warm hospitalities. There are... View all property information
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    From
    $549
    / Night
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    Overview
    Amenities & Details
    • Watersports Nearby
    • Air Conditioning
    • Deck
    • Satellite TV
    • Private Fishing...
    • There Are Tennis...
    • Stereo System
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Cranford on the Miles is a waterfront home located on 3+ acres, in St. Michaels. Fully renovated, with Wi-Fi, there is a Master Bedroom with king bed, sitting room, and private balcony; Second Bedroom with a double bed; Third Bedroom with both a double and twin bed; and a Den with a trundle bed... View all property information
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    From
    $1,829
    / Night
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    Overview
    Amenities & Details
    • Private Outdoor...
    • Private Fishing...
    • Water Views
    • Playground
    • Private Tennis Court
    • Internet Access
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Secluded, tranquil home located on the water, between Easton and Oxford, Maryland. Includes five bedrooms, four bathrooms, fully equipped kitchen, sun porch, swimming pool and tennis courts. Grounds include private driveway, miles of walking paths, and dock with two kayaks. View all property information
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    From
    $232
    / Night
    View Details
    Overview Reviews (1)
    Amenities & Details
    • Satellite TV
    • Refrigerator
    • Water Views
    • Grill
    • Washer
    • Air Conditioning
    • Internet Access
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The historic and recently restored Thomas Blades House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, parks, restaurants, town pool, library, churches and shops in St. Michaels. The house was built around 1850 by Thomas Blades, a young sailor.... View all property information
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    5 of 5 stars Reviewed 18 August 2014
    Location location location! Walk to perhaps the cutest town ever! Friendly people ,dog loving community, sail boats, restaurants and such a lovely little town.. Perfection found!
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    From
    $366
    / Night
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    Overview Reviews (3)
    Amenities & Details
    • Private Outdoor...
    • Stereo System
    • Dryer
    • Satellite TV
    • Washer
    • Waterfront
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This house is on the former estate of John Raskob, builder of the Empire State Building. The four-bedroom, two-bath house is one of seven that Raskob built for his farm employees. Now it has its own dock and swimming pool fronting on Grove Creek, with access to the Chester River and Chesapeake... View all property information
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    From
    $427
    / Night
    View Details
    Overview Reviews (2)
    Amenities & Details
    • Dryer
    • Internet Access
    • Air Conditioning
    • Washer
    • Stereo System
    • Waterfront
    • Water Views
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The historic Thomas Harrison House is located on the harbor in the center of the town of St. Michaels. This Eastern Shore/Chesapeake Bay vacation rental has magnificent water VIEWS and can accomodate up to 12 people. The house is a short walk from all the museums, parks, restaurants, churches, and... View all property information
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    5 of 5 stars Reviewed 27 September 2014
    Friends and family stayed at the home to watch my nephew get married on 9/20/14. I must say, the house was as much of the event as the wedding celebration. We went from 6 of us...
    5 of 5 stars Reviewed 23 July 2014
    Our daughter was married at the Tidewater Inn in Easton. We rented this lovely, large home the week before the wedding to have a place for the bride to relax while we spent time...
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    From
    $220
    / Night
    View Details
    Overview Reviews (12)
    Amenities & Details
    • Refrigerator
    • Patio
    • Fireplace
    • Water Views
    • Internet Access
    • Waterfront
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The recently restored historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, town pool, parks, restaurants, library, churches and shops in St. Michaels. The house was built around 1840 by Washington Melson, a sailor,... View all property information
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    5 of 5 stars Reviewed 22 August 2014
    The pictures of this house do not lie. It is that nice. We parked our car and didn't need again until we left. Close to everything. Walk to the water , sit on the bench and...
    5 of 5 stars Reviewed 20 July 2014
    We fully enjoyed our relaxing stay in the sleepy little town of St. Michaels, and would definitely return when given the chance. The location is perfect - within a one block walk...
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    From
    $610
    / Night
    View Details
    Overview
    Amenities & Details
    • Stereo System
    • Boat Available
    • Elevator/Lift access
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    • Private Fishing...
    • Water Views
    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
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    From
    $701
    / Night
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    Overview
    Amenities & Details
    • Satellite TV
    • Dryer
    • Waterfront
    • Deck
    • Stereo System
    • Washer
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    From
    $305
    / Night
    View Details
    Overview
    Amenities & Details
    • Washer
    • DVD Player
    • Air Conditioning
    • Grill
    • Water Views
    • Wi-Fi
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy a week at this OCEAN BLOCK 6 bedroom home sleeping 17 people. Just steps to the board walk and downtown, this home will serve as your base in S. Rehoboth where you can enjoy the public, guarded beach and all that downtown Rehoboth has to offer including a fantastic range of restaurants and... View all property information
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    From
    $549
    / Night
    View Details
    Overview
    Amenities & Details
    • Fireplace
    • Hot Tub
    • Boat Available
    • DVD Player
    • Deck
    • Washer
    • Stereo System
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    From
    $341
    / Night
    View Details
    Overview
    Amenities & Details
    • Dryer
    • Fireplace
    • Internet Access
    • Deck
    • Washer
    • Balcony
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
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