We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Preston Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $398 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travelers get your favorite Preston area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 15 Rentals in Preston
    Sort by:
    Default
    Preston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Preston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 15 miles of Preston.
    Waterfront Vacation Home with Private Beach1 / 55
    (5)Average
    Trappe
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    RESTORED WATERFRONT COTTAGE1 / 24
    (10)Excellent
    Royal Oak
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Royal Oak, Talbot County 21662
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Royal Oak
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Waterfront
    • Grill
    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...
    View all property information
    Location Information
    Royal Oak, Talbot County 21601
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Waterfront Room Rentals 1 with Private Beach1 / 34
    (1)Very good
    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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.
    See all reviews
    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...
    View all property information
    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Waterfront Room Rentals 2 with Private Beach1 / 40
    (1)Very good
    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths1 / 40
    (13)Very good
    Cambridge
    6 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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 September 3, 2019
    Perfect family retreat. We were six adults and eight children in three generations. This is a vacation we do each year in a different home. This home/property was...
    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...
    See all reviews
    About this property
    Saddle Beach - Extended families and groups love our 7 Bedroom, 5 Ba luxury home! 5+ acres, wide water riverfront, sandy beach, dock & pool, boats & bikes. Beautiful, newer custom 3-story waterfront home w/ deep wrap around porches, 6/7 bedrooms w/ 5 baths & can accommodate up to 20 guests*....
    View all property information
    Location Information
    Cambridge, Maryland 21677
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 20
    Cambridge
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Save time - get the best Preston rentals sent straight to your email!
    Get the List
    Year Round Estate on Bay / Fam. Reunions / Slps 281 / 35
    (15)Excellent
    Cambridge
    7 Bedrooms, 7 Bathrooms, Sleeps 28 Quick View
    Check in Check out
    Show Prices
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 28
    Easton
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Easton, Talbot County 21601
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Bethlehem
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Yard
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    TOTALLY PRIVATE, enjoy nature and Relax at Little Creek Hideaway, perfect family getaway during any season. 10 mins from Easton, property will make you feel like you're miles away from life's hustle and bustle. Two kayaks , outdoor fire-pit. Stocked kitchen, dining room with seating for 6, game...
    View all property information
    Location Information
    Bethlehem, Maryland 21655
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Cambridge
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover the charms of Cambridge and Delmarva while staying in this lovely colonial vacation rental house! With 4 bedrooms and 3.5 baths, a group of 12 can unwind in 2,700 square feet of living space after adventures in the Cambridge area. Between 3 roomy living areas, a welcoming wraparound porch,...
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
    Cottage at Heron Cove, Chesapeake Bay, Cambridge1 / 50
    (11)Excellent
    Cambridge
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Porch
    • DVD Player
    • Parking
    • Waterfront
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 16, 2019
    The location is out of the way but not to far from the action in Cambridge. Crabbing and fishing was amazing. Water on the back creeks off the Little Choptank are made for...
    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...
    See all reviews
    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....
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Preston Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers

    Top-rated Preston Things to Do

    Browse all things to do

    Additional Preston Info

    Go to map view
    • Local time: 06:46 PM (EDT)
    List your property
    Owner log in