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Preston Family & Kid Friendly Rentals

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    Don't let other travelers get your favorite Preston area vacation rental. You're so close to securing your perfect getaway. Book today.
    15 Matching Rentals in the Preston AreaView all 17 rentals
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    Preston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Preston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    The following rentals are within 20 miles of Preston.
    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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    RESTORED WATERFRONT COTTAGE1 / 24
    (10)Excellent
    Royal Oak
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You can tell right away, from the warm sage green exterior and the peaceful creekside setting, that this charming vacation cottage promises a fun, relaxing getaway. With a 180 degree expanse of spectacular Oak Creek waterfront, the River House at Royal Oak is the pefect choice for year 'round...
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    Royal Oak, Talbot County 21662
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1,250 Sq Ft BARN RETREAT-2BR,BEACH 17MILES JACUZZI/ PETS1 / 150
    (6)Very good
    Greenwood, DE
    2 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Amenities & Details
    • 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 March 23, 2018
    This place is so wonderful for a quiet retreat off season. Don't pass this by.. I found it to be everything and more than what I needed, and then some!. the natural light, in...
    Reviewed January 13, 2018
    We had to come back. Each visit top notch! The pictures say it all. They clearly work hard to meet every need.
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    About this property
    Our renovated barn is the perfect place for you, family and friends to relax, rejuvenate, play, create and have fun to your hearts content:). Total privacy, peace and quiet in Rural Delaware. Pack light and just bring clothes and food as we have everything you and your crew will need!! Your Hay...
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    Location Information
    Greenwood, Delaware 19950
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 10
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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 July 23, 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 August 26, 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    Sun and Sand Loft- just minutes to the beach:) Hot tub1 / 127
    (4)Excellent
    Greenwood, DE
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Certificate of Excellence
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    Amenities & Details
    • Private Yard
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 4, 2018
    Connie's place was amazing she is so hospitable ,and her place is undescribable.. I would love to stay again any time Iam in Delaware.
    Reviewed January 13, 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!
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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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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Easton
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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
    Rental Home - 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
    • 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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    Location Information
    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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    Amenities & Details
    • 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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    Location Information
    Royal Oak, Talbot County 21601
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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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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    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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    Wye Mills
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Private Yard
    • Secure Parking
    • Air Conditioning
    • 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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    Location Information
    Wye Mills, Talbot County 21679
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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