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Ridgely Vacation Rentals

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    All 28 Rentals in Ridgely
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    The following rentals are within 40 kilometres of Ridgely.
    ROMANTIC PRIVATE APARTMENT GETAWAY- 17 Miles to BEACHES & BAY--Pets!!1 / 140
    (2)Excellent
    Farmington, DE
    1 Bedroom, 1 Bathroom, Sleeps 12 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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    Retreat at a quiet, water front cottage1 / 14
    (3)Very good
    Chestertown
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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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    Sailors Crossing1 / 12
    (3)Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 September 2017
    Beautiful home with many amenities, clean and comfortable. Awesome screened-in porch, great place to enjoy your morning coffee. Community park right behind home with tennis...
    Reviewed 15 August 2017
    House was great. Plenty of room to hang out and have fun with a large group and the grill was a plus. Just down the street from an awesome restaurant on the water and a short...
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    About this property
    Sailors Crossing is a 3 bedroom, 2 bath home located in the heart of Rock Hall. The dining room seats 6 and the kitchen is roomy enough for several cooks and helpers. If it's crab you're after, the screened porch provides enough room for the group or take the feast out to the backyard, there's...
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    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    288 SF TREETOP NATURE RETREAT- PRIVATE- 17 MILES TO BEACH1 / 135
    (5)Very good
    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 13 January 2018
    We had to come back. Each visit top notch! The pictures say it all. They clearly work hard to meet every need.
    Reviewed 23 November 2017
    My family and I spent several nights. The nearest beach is about 20 miles and visited during the day. In the evenings we enjoyed the countryside of Delaware- campfires, biking...
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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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    Greenwood, Delaware 19950
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 16
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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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    Amenities & Details
    • 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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    Waterfront Cottage at Spring Cove1 / 15
    (2)Very good
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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    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...
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    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Amenities & Details
    • 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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    Location Information
    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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    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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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 1 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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    Charming Apartment in Historic Chestertown, MD1 / 10
    (7)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    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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    Centreville, Maryland 21617
    Holiday Rental House - 4 Bedrooms, 2 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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    Easton, Talbot County 21601
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    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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    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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    Cozy Apartment in Chestertown1 / 7
    (1)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
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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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    Sun and Sand Loft- just minutes to the beach:) Hot tub1 / 122
    (3)Excellent
    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 13 January 2018
    Connie did a fantastic job setting up this place and worked hard to make our stay perfect. We loved it and can't wait to come back!
    Reviewed 23 November 2017
    This is a nice quiet residence and the property is beautiful. We went to several beach's, Dog Fish Brewery and hiking. Hostess was accommodating and helpful.
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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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    Greenwood, Delaware 19950
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Rock Hall
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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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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    Rock Hall, Maryland 21661
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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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 & Spacious Chestertown Home1 / 25
    (3)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 30 December 2017
    The home was very clean and comfortable. It was very convenient and well set up for 3 generations to stay during our visit to Washington College. Chestertown and Rock Hall...
    Reviewed 20 November 2017
    This property is beautifully appointed. Every amenity possible to make you feel at home. Pool is clean and well maintained. A PLUS!!
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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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    Chestertown, Maryland 21620
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Preston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Shared Indoor Pool
    • Private Garden
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    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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    Wye Mills
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Washer
    • Private Garden
    • Secure Parking
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    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique apartment sleeps 5 and is part of the elegant house sitting on 17 private acres in historic Wye Mills with access to a lake. This place is perfect for kayaking, fishing and an overall countryside experience abundant with wildlife. Wye Mills is home to the historic Old Wye Grist Mill...
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    Wye Mills, Talbot County 21679
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Belle Rose Cottage at Victory Farm (Pet Friendly!)1 / 17
    (2)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This cottage is a little piece of heaven. Everything you need for a short- or long-term stay is right at your fingertips: a full-sized kitchen, living room, bedroom, and a...
    Reviewed 4 weeks ago
    This cottage just begs you to slow down and relax. Gorgeous sunsets coupled with interesting sights of a real farm make this cottage picture perfect... we found neat shops and...
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    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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    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Centreville
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
    • Air Conditioning
    • Private Garden
    • Washer
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning upscale private apartment that sleeps 3. Located in a private setting at Wye Branch Manor. Less than 10 miles to golf, outlet shopping, hiking trails and the Wye River. 15 miles to historic Easton, 20 minutes to Saint Michael's and Oxford. The apartment is 1 mile from Wye Mills, there is a...
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    Location Information
    Centreville, Maryland 21671
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Preston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Garden
    • Air Conditioning
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    • DVD Player
    • Shared Indoor Pool
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    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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