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Holiday Rentals and Homes in Ridgely, MD

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    The following rentals are within 40 kilometers of Ridgely, Maryland.

    1 / 28
    5 of 5 bubbles (3) Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 21
    5 of 5 bubbles (1) Excellent
    Chestertown
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 12
    Grasonville
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    1 / 14
    4.5 of 5 bubbles (3) Very good
    Chestertown
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • Air Conditioning
    • Grill
    • DVD Player
    • Washer
    • Patio
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Chestertown, Maryland 21620
    3 of 5 bubbles 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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    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 21662
    1 / 26
    5 of 5 bubbles (1) Excellent
    Stevensville
    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 21666
    5 of 5 bubbles 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 / 55
    3 of 5 bubbles (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 21673
    4 of 5 bubbles 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 bubbles 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 / 11
    4 of 5 bubbles (2) Very good
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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 bubbles 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 bubbles 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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    1 / 11
    Stevensville
    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 21666
    1 / 10
    5 of 5 bubbles (6) Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Terrace
    • Balcony
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 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 bubbles 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 bubbles 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 / 12
    5 of 5 bubbles (1) Excellent
    Rock Hall
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • 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 21661
    5 of 5 bubbles Reviewed 2 January 2017
    Lovely, comfortable,clean, friendly with direct access to dock and bay. Lovely views from the many windows. Space is bright and modern while still sortingva large claw foot tube...
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    1 / 15
    4 of 5 bubbles (2) Very good
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
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    • 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 bubbles 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 bubbles 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 / 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 21601
    1 / 29
    5 of 5 bubbles (1) Excellent
    Trappe
    8 Bedrooms, 7 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
    • x
    • 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 21673
    5 of 5 bubbles 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 / 28
    Farmington, DE
    1 Bedroom, 1 Bathroom, Sleeps 8 | Quick View
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    • Patio
    • Washer
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Grill
    • Hot Tub
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Studio apartment getaway private entry w/ jacuzzi and private entrance in wooded rural central De on 80 acre organic farm. Visit beaches, restaurants and shopping during the day and enjoy Delaware's peaceful countryside in the evening. Kids & pet friendly:) This beautiful studio apartment has... View all property information
    Location Information
    Farmington, Delaware 19950
    1 / 17
    5 of 5 bubbles (3) Excellent
    Rock Hall
    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 21661
    1 / 10
    Rock Hall
    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 21661
    1 / 16
    Preston
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Secure Parking
    • Shared Indoor Pool
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    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 21655
    1 / 16
    5 of 5 bubbles (1) Excellent
    Chestertown
    4 Bedrooms, 9 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • 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 21620
    5 of 5 bubbles 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 / 34
    Centreville
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Internet Access
    • Porch
    • Satellite TV
    • Grill
    • Waterfront
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This house is on the 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 two-mile-wide Chester River and... View all property information
    Location Information
    Centreville, Maryland 21617
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    1 / 41
    Trappe
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Air Conditioning
    • Parking
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    • 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 21673
    1 / 12
    Stevensville
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
    • Private Garden
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Watch the beautiful sunrise and sunset from the privacy of the guest house. House has separate entrance for your privacy. 3 bedrooms and 2 full bath - with a spa bath in the master bath. Ample living room with ample dining and kitchen areas. Guests can enjoy their home cooking as kitchen is fully... View all property information
    Location Information
    Stevensville, Kent Island 21666
    1 / 20
    Preston
    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 21655
    1 / 24
    Greenwood, DE
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Awesome loft bedroom nestled in woods in rural De on 80 acre organic farm. Best of both worlds***Visit the beach,restaurants & shopping during the day. Enjoy peaceful country life in the evening. Kids & pet friendly. Outdoor jet tub and shower . Atlantic beaches 29miles Loft Space with Bright,... View all property information
    Location Information
    Greenwood, Delaware 19950
    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 21673
    1 / 34
    Trappe
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Private Garden
    • Parking
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    • 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 21673
    1 / 7
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Chestertown, Maryland 21620