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Holiday Rentals in Woolford

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    All 27 Rentals in Woolford
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    Woolford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    The following rentals are within 30 kilometres of Woolford.
    Best kept secret by the bay (Entire House)1 / 20
    (4)Excellent
    Fishing Creek
    3 Bedrooms, 2 Bathrooms, Sleeps 4 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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    Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths1 / 31
    (12)Very good
    Cambridge
    6 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    Amenities & Details
    • Hot Tub
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Sauna
    • Private Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 July 2016
    Our family gathering was everything we hoped because of this vacation home. The house met the needs for the 13 of us, from 4 to 67 years old. We especially loved the different...
    Reviewed 1 April 2014
    We had a group of 9 women stay here for a crafting weekend. The house was perfect for us. We brought a few folding tables and were able to all be in the large open rooms...
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    About this property
    Fabulous, recently-built premier vacation home on 500 feet of Chesapeake waterfront. A gorgeous home; beach, dock, private pool, boats, bikes, porches & mile-wide view With 6 acres of property, wide water & sandy beaches, this private luxury vacation rental is minutes from Cambridge,...
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    Cambridge, Maryland 21677
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
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    Waterfront Room Rentals 1 with Private Beach1 / 34
    (1)Very good
    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
    Reviewed 3 September 2018
    Dimitri was very kind and helpful. We throughly enjoyed our stay. The view of the Choptank was beautiful.
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    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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    Cottage 2 at Grandview Pleasure Point1 / 9
    (1)Excellent
    Bozman
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Porch
    • Patio
    • Grill
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas fireplaces,...
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    Bozman, Talbot County 21612
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Royal Oak
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Central Heating
    • Grill
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Ingleton! Relax by the pool. Fish or crab or picnic at the end of the pier. Do all three. Go biking. Go hiking. Go boating. Visit historic St. Michaels, Easton and Oxford. Watch the sunset from the Adirondack chairs at the water's edge. Eat. Shop. Play golf. Play yard games. Play board...
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    Royal Oak, Talbot County 21601
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    St. Michaels Waterfront Home W/Dock for 2 boats1 / 18
    (1)Excellent
    Neavitt
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Balcony
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2017
    VERY nice place and owner was excellent. Place building is old must has been well maintained. It is very clean and exceeded all our needs. Owner are excellent people!!
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    About this property
    Full renovations just completed on this newly-listed historic waterfront home. Sleeps five (1 King, 1 Queen, 1 Twin). Kick back, relax and enjoy the beautiful waterviews. Have crabs on the deck or cocktails on the dock. Features a new dock with 14 ft. and 16 ft. wide, deepwater boat slips. Bring...
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    Location Information
    Neavitt, Talbot County 21652
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Cedar Beach Lodge is a Modern Year-Round1 / 8
    (2)Excellent
    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Porch
    • Internet Access
    • Grill
    • Parking
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 January 2018
    We rented this beautiful, well-kept and well-stocked lodge for a week-long family vacation. Deborah was excellent to work with and accommodating. The house offers plenty of...
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    About this property
    Cedar Beach Lodge is a modern, smoke free, year-round retreat located in the desirable and private Cove Point Beach Community on the western shore of the Chesapeake Bay. It is conveniently located 1 hour from Annapolis, MD and Washington, DC on Route 4 and 10 minutes from Solomon's Island, MD....
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    Lusby, Calvert County 20657
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chesapeake Bay Waterfront on Hoopers Island with Private Beach1 / 32
    (2)Very good
    Fishing Creek
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Jerry is a wonderful host and was flexible with our check-in time. The house was spotless when we arrived, and the kitchen and cookware was well stocked. The house resides a few...
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    About this property
    This lovely home offers all the comforts of home, including a covered porch where you can meditate, read, paint, bird watch and get away from it all, as the quiet natural beauty of the area makes it the perfect retreat! The house features spectacular views of the bay and sunsets from the first...
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    Location Information
    Fishing Creek, Maryland 21634
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge1 / 20
    (6)Excellent
    Tilghman
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Waterfront
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 2016
    We had an absolutely wonderful time. The cottage was clean and well appointed. We would definitely go back!
    Reviewed 8 October 2015
    Tilghman Cottage (the Roost) is a lovely place that makes you feel comfortable in every possible way. The house is very clean, bright, cosy, and yet spacious, fully equipped...
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    About this property
    Enjoy the beauty and tranquility of Tilghman Island from this bright and comfortable 3 bedroom, 2 bathroom cottage known for many years as the vacation rental 'The Roost.' Available for both short and long-term rentals, the cottage is located on a quiet residential street across from a marina...
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    Tilghman, Talbot County 21671
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Hoopers Island Studio, 360 Degrees WATER VIEWS1 / 38
    (3)Excellent
    Fishing Creek
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • Patio
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2018
    Memories of the peace, beauty and comfort of Fishing Creek, Maryland and of the sparkling, colorful Queen Anne Cottage that is Hoopers Island Haven warm my cold winter days! If...
    Reviewed 13 August 2014
    We came to this historic area to do some fishing. The house was well equipped with emphasis to detail. A great deal of creativity is evident once you step inside. You find...
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    About this property
    360 Degree Views, WATERFRONT Scenic, peaceful and spacious studio apartment located on the entire second floor of our property. AVAILABLE FOR 2 NIGHT STAY MINIMUM, sorry NO EXCEPTIONS 3rd person $25 extra per night *Ironman/Eagleman/Event/Holiday: 3 Night minimum Discounted weekly rates....
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    Fishing Creek, Maryland 21634
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Comfortable, Spacious & Fun! 6 Acres Pool & Shore1 / 36
    (3)Very good
    Wittman
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 2016
    My family was looking for a vacation house that would meet the needs of the entire family. One of the reasons we picked this place was the picture and description of the beach...
    Reviewed 28 October 2015
    It was a long weekend, so packed our bikes up on Saturday rather fighting traffic on Friday evening. I guess it worked because our trip was fast and smooth. With the...
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    About this property
    Pool, Shoreline, Small Private Beach, Acreage, Lawn, Barbecue, and Nature. Spacious 6000+ square foot home. Up-to-date Gourmet Kitchen. Large and Open Common Spaces. Wall of Glass Overlooking the Chesapeake. 4 Master Suites with Attached Bathrooms and Each with King Bed, Day Bed and Trundle...
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    Wittman, Talbot County 21676
    Cabin Holiday Rental - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Bozman
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambiance of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, new sleep sofas, wing chairs and sleeper lounge chairs, as well as antiques, reproductions and other eclectic furnishings All the...
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    Bozman, Talbot County 21612
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Bozman
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, new sleep sofas, wing chairs and sleeper lounge chairs, as well as antiques, reproductions and other eclectic furnishings All the...
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    Location Information
    Bozman, Talbot County 21612
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cottage at Heron Cove, Chesapeake Bay, Cambridge1 / 50
    (10)Excellent
    Cambridge
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Porch
    • DVD Player
    • Parking
    • Waterfront
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 July 2018
    If you enjoy fishin, crabbing, kayaking, smores by campfire, wildlife and peace and quite this is the place for couples and families.Additionally, close to town, supermarket...
    Reviewed 20 January 2018
    The Cottage has been our vacation get-away now for the last 6 years and we are planning to return again this year. Our children (one in college and one post college) still love...
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    About this property
    DEAL DIRECTLY WITH THE PROPERTY OWNER AND AVOID ANY ONLINE BOOKING FEES CHARGED BY HOMEAWAY, VRBO OR VACATIONRENTALS The Cottage at Heron Cove is a cozy home situated on a scenic peninsula with water views from every window. Awake each morning to watch the sun glisten off the gentle waters....
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    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Fishing Creek
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Housekeeping Included
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious Historic Home. Wide open water views on both sides of the house! Come to discover 'Hoopers Hill'. Relax between waterfront sunrise and waterfront sunset. Gourmet kitchen, private beach, starry evening skies, and quiet reading spaces await. Shoreline crabbing, oystering and fishing too....
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    Fishing Creek, Maryland 21634
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Year Round Estate on Bay / Fam. Reunions / Slps 281 / 35
    (15)Excellent
    Cambridge
    7 Bedrooms, 7 Bathrooms, Sleeps 28 Quick View
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Internet Access
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2016
    Lovely setting & a great location for sure. Nice big comfortable house. Great spot for big family reunion. This was our 2nd time we stayed here. Loved our first visit a...
    Reviewed 3 August 2012
    I would not change a single thing. Our family enjoyed the six day stay at this awesome place. The amenities were great, the location was central to other sights, and the...
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    About this property
    Captains Quarters on the Bay is a wonderful waterfront home with over 6,000+ Sq. Ft. of Living Space. Designer Appointed with All New Furnishings.7 Bedrooms with 6 Full Bathrooms, some with Jacuzzi/Whirlpool Baths. Gourmet Kitchen with Six Burner Stovetop and Triple Ovens. Large Game Room with...
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    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 28
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    Cambridge
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Washer
    • Terrace
    • Parking
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the beautiful Eastern Shore of Maryland, Cambridge has been named one of the best ten small towns in the U.S. and is a boater's dream! The house has four private suites, full gourmet kitchen, three sitting areas, and two car garage. Check out the Dorchester County Tourism page for...
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    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Main House at Grandview at Pleasure Point1 / 34
    (12)Excellent
    Bozman
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    What a terrific week we had . Young and old enjoyed our stay. Perfect weather and plenty of crabs made our visit special. Grandview is the perfect family vacation spot.
    Reviewed 19 June 2018
    The drive way to Grand View Cottages is gravel right beside a cemetery on the left of MD 579-S. I am describing this so you would not pass it thinking the next asphalted...
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    About this property
    Main House: Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large living room, dinning room, screened porch,...
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    Location Information
    Bozman, Talbot County 21612
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Waterfront
    • Internet Access
    • Parking
    • Outdoor Dining Area
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a peaceful beach getaway? Located in quiet Long Beach overlooking Flag Harbor Yacht Haven marina, this cottage is a few minutes walk to the sandy beach along cliffs famous for fossils from the Miocene. The shallow water is safe for children to swim, and a favorite for fishermen and...
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    Saint Leonard, Calvert County 20685
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cambridge
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Balcony
    • Parking
    • Cable/satellite TV
    • Terrace
    • Washer
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern home that has accommodations for more than 10+, with 2 full living room areas, 3 and half baths, Xfinity cable, with flat screen TVs in each of 5 bedrooms. Master with 50', mini fridge, sofa,loveseat, and ensuite master bath. Home is minutes away from some of the finest Eastern Shore Seafood...
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    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Lusby
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you traveling for business or just for vacation? If so my one bedroom in-law suite w/ a large walk in closet, spacious living room, one full bathroom w/ access to a washer/dryer should be a perfect fit. For vacation 15-20mins from local waterfront restaurants/bars. Local attractions include...
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    Location Information
    Lusby, Calvert County 20657
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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