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Woolford Vacation Rentals

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    Don't let other travelers get your favorite Woolford area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 17 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 15 miles 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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    Waterfront Vacation Home with Private Beach1 / 55
    (5)Average
    Trappe
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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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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    • Wi-Fi
    • Parking
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 3, 2018
    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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    Fishing Creek, Maryland 21634
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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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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    Amenities & Details
    • Private Yard
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 3, 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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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Parking
    • Private Yard
    • 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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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Yard
    • 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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    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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 July 12, 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 April 1, 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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    Location Information
    Cambridge, Maryland 21677
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 20
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    Hoopers Island Studio, 360 Degrees WATER VIEWS1 / 38
    (4)Excellent
    Fishing Creek
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This place was truly breathtaking. The drive from Cambridge, alone, is worth the trip. I was competing in an Ironman triathlon, and this place was easily one of the best finds...
    Reviewed January 16, 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...
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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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    Location Information
    Fishing Creek, Maryland 21634
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Cambridge
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • 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
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Cambridge
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Parking
    • Cable/satellite TV
    • Terrace
    • Washer
    • Private Yard
    • 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
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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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 April 30, 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 August 3, 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
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 28
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    Fishing Creek
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Location Information
    Fishing Creek, Maryland 21634
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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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 July 11, 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 January 20, 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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Cambridge
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover the charming city of Cambridge while staying in this lovely colonial vacation rental house. With 3 bedrooms and 2.5 bathrooms, a group of 7 can unwind in 2,068 square feet of living space after adventures in the Cambridge area. Between 2 roomy living areas, a welcoming wraparound porch,...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Fishing Creek
    7 Bedrooms, 3 Bathrooms, Sleeps 17 Quick View
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    Amenities & Details
    • Terrace
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The historic Queen Anne Victorian vacation rental home is the perfect, quiet respite for friends and family. With 7 bedrooms, 2.5 baths, and views of the Chesapeake Bay from almost every window, this scenic home is perfect for up to 17 guests looking to getaway. Updates and amenities provide...
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    Location Information
    Fishing Creek, Maryland 21634
    Rental Home - 7 Bedrooms, 3 Bathrooms, Sleeps 17
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    Cambridge
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Luxurious Duplex can sleep up to 5 people. Having recently undergone a full renovation with all contemporary fittings and fixtures, it is now in stunning condition. It has a brand new kitchen, double-glazed windows and converted loft. The master bedroom features a king-size bed, whilst the...
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    Location Information
    Cambridge, Maryland CB1 3QR
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Woolford Flight and Weather Info
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    52° 35°
    November
    44° 28°
    December
    39° 25°
    January
    42° 26°
    February

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