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Holiday Rentals in Ridgely

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    All 27 Rentals in Ridgely
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    The following rentals are within 40 kilometers of Ridgely.
    Waterfront Cottage at Spring Cove1 / 15
    (2)Very good
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    RESTORED WATERFRONT COTTAGE1 / 24
    (10)Excellent
    Royal Oak
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Sailors Crossing1 / 12
    (3)Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Retreat at a quiet, water front cottage1 / 14
    (3)Very good
    Chestertown
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Air Conditioning
    • Grill
    • DVD Player
    • Washer
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    About this property
    Located close to both Chestertown (15 minutes) and Rock Hall (30 minutes), MD this quiet, simple but energetic space is an ideal gathering place for families and friends. Stay here and relax the entire visit or explore the many activities, restaurants and cultural venues available in the Kent...
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    Chestertown, Maryland 21620
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Captain's Quarters, a waterfront  couples retreat1 / 12
    (1)Excellent
    Rock Hall
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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...
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    Rock Hall, Maryland 21661
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    * 3 Bedroom Rental House in Historic Rock Hall MD1 / 17
    (3)Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Chester River House with Views1 / 11
    (3)Very good
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2017
    The house had amazing views right on the river. It was also very comfortable and in a great location close to the little historic square. Would definitely stay here again and...
    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...
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    About this property
    A 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or just visiting a student at...
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    Chestertown, Maryland 21620
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    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
    Kid 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...
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    Preston, Maryland 21655
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Gorgeous Home on Chester River1 / 16
    (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
    Kid friendly
    Smoking allowed
    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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    About this property
    This gorgeous home is located directly on the Chester River in Chestertown, Md, on the Eastern shore. There are 5 bedrooms, one down and four on the second floor. On the main floor there is a great room that is part kitchen, part TV area and part dining room. Off of this room is a lovely living...
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    Chestertown, Maryland 21620
    Holiday Rental House - 4 Bedrooms, 9 Bathrooms, Sleeps 8
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    Easton
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Waterfront
    • Ocean Views
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Easton, Talbot County 21601
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Bayview by Chesapeake Bay1 / 28
    (3)Excellent
    Chestertown
    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
    Kid friendly
    Smoking allowed
    Reviewed 8 September 2016
    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...
    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...
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    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...
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    Chestertown, Maryland 21620
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Parking
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Waterfront House, Eastern Shore Chesapeake Bay1 / 34
    (21)Excellent
    Centreville
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We welcome your inquiries and would be glad to answer any questions you have before booking. In response to inquiries and booking requests, we will send you our standard rental agreement for your information and approval. This house is on the estate of John Raskob, builder of the Empire State...
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    Location Information
    Centreville, Maryland 21617
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Waterfront Vacation Home with Private Beach1 / 55
    (5)Average
    Trappe
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Parking
    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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...
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    Trappe, Talbot County 21673
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Grill
    • Parking
    • Porch
    • Patio
    Suitability
    Pet friendly
    Kid 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...
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    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Sunview Cottage on Chesapeake Bay1 / 22
    (1)Excellent
    Chestertown
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
    • Grill
    • Parking
    • Outdoor Dining Area
    • Private Garden
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    About this property
    Modern, Cozy 2-Bedroom Cottage with sleeping loft. Views of the Chesapeake Bay from house and wraparound deck. Perfect destination for a couples getaway, family trip or friends gathering to enjoy the Bay & Sunsets. Located in the scenic, serene environs of the Eastern Shore of Maryland in...
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    Chestertown, Maryland 21620
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Charming Apartment in Historic Chestertown, MD1 / 10
    (7)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Balcony
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    This is a lovely upstairs apartment with a super comfy bed, great shower, and everything you would want or need for an easy stay. The cupboards are stocked, you can cook if you...
    Reviewed 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...
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    About this property
    This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An outdoor deck with cafe table and chairs is a nice place to sit on a sunny day. It is perfect for a...
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    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    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
    Kid 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...
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    Preston, Maryland 21655
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    288 SF TREETOP NATURE RETREAT- PRIVATE- 17 MILES TO BEACH1 / 135
    (1)Excellent
    Greenwood, DE
    1 Bedroom, 2 Bathrooms, Sleeps 16 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Ocean Views
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    My family and pet stayed here for three nights. The views were just stunning from the loft. We had a barbecue on the balcony and spent a lot of quality family time. The hostess...
    Reviewed 5 weeks ago
    I recommend this place for nature lovers & dog lovers. Connie provided us champagne, snacks etc. Connie's pet(dog) was great, he would play with us all the time & we all...
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    About this property
    You'll love our renovated horse barn loft. It's the perfect place for family, and friends to getaway and have fun, clear your mind, play and create to your hearts content:)..You will enjoy complete privacy as your parking, walkway and entrance are secluded in natural park like surroundings. Your...
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    Location Information
    Greenwood, Delaware 19950
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 16
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    Farmington, DE
    1 Bedroom, 1 Bathroom, Sleeps 12 Quick View
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    • Washer
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Patio
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    This is the ideal honeymoon location– Totally private and secluded with tons of amenities including, candles and champagne when we arrived. The Jacuzzi was terrific and got...
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    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...
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    Farmington, Delaware 19950
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 12
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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Internet Access
    • Parking
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cozy Apartment in Chestertown1 / 7
    (1)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    This first floor apartment is cozy, sweet, and convenient to everything downtown. A quick 2 block walk brings you to restaurants, shops, galleries, the Farmer's Market on...
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    About this property
    A delightful one-bedroom apartment located in historic Chestertown. Close to Washington College & Heron Point. Apartment accommodates 2 guests. It is the perfect place for enjoying this historic, artistic town on Maryland's Eastern Shore. The space includes kitchen/living room combo, bedroom with...
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    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled behind the main house with a fenced garden, the cottage is a cozy respite after a busy day site seeing or visiting with local friends. Relax and discover the culture, history, nature, and cuisines of Maryland's Eastern Shore. Perfect for folks traveling with a dog or two. Short or long term...
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    Chestertown, Maryland 21620
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Greenwood, DE
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    We had a nice quiet 4 nights here. We brought our bicycles and wrote the quiet country Roads with no traffic. We brought or three dogs and they were able to roam unleashed...
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    About this property
    Awesome loft bedroom nestled in woods in rural De on 80 acre organic farm. Loft Space with Bright, contemporary bedroom and full size loft bunk beds and minimally shared bath, Take a bubble bath in our outdoor jet tub and shower. Delicious Keurigs coffee in the morning. Premium Direct TV with all...
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    Location Information
    Greenwood, Delaware 19950
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cozy & Spacious Chestertown Home1 / 26
    (2)Excellent
    Chestertown
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • Private Garden
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    This property is beautifully appointed. Every amenity possible to make you feel at home. Pool is clean and well maintained. A PLUS!!
    Reviewed 1 week ago
    I was in charge of finding a rental property for our family reunion this year ( no pressure there!). I found Sandybottom and booked it. From start to finish, the interaction...
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    About this property
    Lovely home in a quiet setting very comfortably furnished all you need for a relaxing getaway. Located 7 miles from the center of Chestertown & 5 miles from the center of Rock Hall. This spacious rancher offers four bedrooms two of the four are master suite's, 3 bathrooms, wood burning fireplace &...
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    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Rock Hall
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Parking
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on one of the prettiest streets in Rock Hall, the Bay Cottage offers 2 bedrooms and 1 full bathroom. A fully equipped kitchen, gas grill and outdoor seating pulls the family together for mealtimes or enjoy our local restaurants which are just a short walk. Pets are welcomed on this fenced...
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    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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