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.
TripAdvisor
Woolford
Post
Inbox
Search

Woolford 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
    C$444 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Woolford area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 15 Rentals in Woolford
    Sort by:
    Default
    Woolford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    The following rentals are within 25 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
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Waterfront Vacation Home with Private Beach1 / 55
    (5)Average
    Trappe
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Chesapeake Bay Waterfront on Hoopers Island with Private Beach1 / 35
    (3)Very good
    Fishing Creek
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 23, 2019
    Enjoyed this property as a place to reconnect with old friends. Enjoyed views of the bay from the porch, stargazing, biking, walks. Small private beach. Old Salty’s next...
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Fishing Creek, Maryland 21634
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Waterfront Room Rentals 1 with Private Beach1 / 34
    (1)Very good
    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • 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 travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Hoopers Island Studio, 360 Degrees WATER VIEWS1 / 38
    (4)Excellent
    Fishing Creek
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Parking
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2018
    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...
    See all reviews
    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....
    View all property information
    Location Information
    Fishing Creek, Maryland 21634
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    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
    Payment Protection
    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
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 28
    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 travellers 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
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
    Save time - get the best Woolford rentals sent straight to your email!
    Get the List
    Fishing Creek
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    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....
    View all property information
    Location Information
    Fishing Creek, Maryland 21634
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    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 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...
    View all property information
    Location Information
    Cambridge, Maryland 21613
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    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
    Holiday Rental House - 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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Fishing Creek
    7 Bedrooms, 3 Bathrooms, Sleeps 17 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Fishing Creek, Maryland 21634
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 17
    List your property
    Owner log in