Woolford vacation rentals

We found 141 vacation rentals — enter your dates for availability

Discover a selection of 6 homes and other vacation rentals in Woolford that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the amenities you need and want for your stay, which might include a garden and WiFi. You'll be sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Woolford

Showing deals for:Jul 24 - Jul 31

Image gallery for New Island Home on the Chesapeake Bay Sunsets

Exterior
10 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

New Island Home on the Chesapeake Bay Sunsets

Church Creek

9% off
Price is $602
$4,213 for 7 nights
All fees included
New Island Home on the Chesapeake Bay Sunsets

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Find out more about Woolford

Find the perfect vacation rental for your Woolford getaway

Experience the unique character of Woolford with a stay in a vacation home rental. This city has something for everyone. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Woolford

Are you hoping to find attractions to see while you're in town? Venture out of your vacation home and experience everything that makes Woolford a fun place to get away. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Layton's Chance Vineyard and Winery (14.9 mi / 24 km)
  • Phillips Wharf Environmental Center (16.8 mi / 27 km)
  • Bay Country Shop (7.7 mi / 12.4 km)
  • Chesapeake Hills Golf Course (15.6 mi / 25.1 km)

Exploring the natural landscape of Woolford

Whether you're an active traveler or just want to take in the scenery, Woolford is a great place to get out in nature. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Blackwater National Wildlife Refuge (6.5 mi / 10.5 km)
  • Long Wharf Park (7.8 mi / 12.5 km)
  • Gerry Boyle Park at Great Marsh (7.9 mi / 12.7 km)
  • Flag Ponds Nature Park (15.6 mi / 25.1 km)
  • Matoaka Beach (16.2 mi / 26 km)
  • Ragged Island (5.6 mi / 8.9 km)

Transportation options to and around Woolford

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 22.3 mi (35.8 km) from the city center.

Frequently asked questions

What is the best area to stay in Woolford, Maryland, United States of America when booking a vacation rental?
When looking for the best area to stay in Woolford, Maryland for a vacation rental, consider the charming neighborhoods near the water, which offer a serene atmosphere and picturesque views. One popular spot is along the Choptank River, where you can find a variety of properties that cater to different tastes, from cozy cottages to spacious homes. This area is superb for those who enjoy outdoor activities, as it provides easy access to boating, fishing, and scenic walks along the riverside.

Another appealing neighborhood is close to the historic sites of the region, allowing guests to immerse themselves in the rich history of Maryland's Eastern Shore. You'll find attractions such as local farms that offer tours and fresh produce, as well as quaint shops and restaurants that capture the essence of small-town charm.

With several rental options available in these neighborhoods, visitors can easily find a comfortable place to stay that suits their needs.
How much does it cost to rent a vacation home in Woolford?
Prices for vacation rentals in Woolford vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Woolford to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Woolford vacation house rentals?
You can find great discounts on house rentals in Woolford on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Woolford?
For renting a beach house in Woolford, travelers should focus on the nearby areas along the Chesapeake Bay, particularly in the towns of Cambridge and Easton. The waterfront properties in Cambridge often come with stunning views of the bay and access to private docks, making them ideal for boating enthusiasts. Many of these homes feature spacious decks, outdoor grills, and amenities like kayaks and bicycles for exploring the area.

In Easton, visitors can find charming beach houses that are close to public beaches and parks, offering amenities such as modern kitchens, cozy living spaces, and outdoor fire pits for evening gatherings. The proximity to local restaurants and shops adds to the convenience of staying in this area.

Additionally, the nearby Blackwater National Wildlife Refuge provides opportunities for nature lovers, with rentals often located just a short drive away, allowing easy access to hiking trails and birdwatching spots.
What is the most popular type of vacation rental accomodation in Woolford?
In Woolford, vacation houses are the most popular type of rental accommodation, with several available throughout the area. These properties typically feature spacious interiors with multiple bedrooms, fully equipped kitchens, and comfortable living areas—great for families or groups looking to enjoy a peaceful getaway. Many vacation houses also include outdoor spaces such as decks or gardens, providing a serene environment to relax and appreciate the natural surroundings.
Are there any family house rentals in Woolford?
In Woolford, Maryland, there are several family-friendly house rentals available, making it a suitable destination for those traveling with children. Many of these homes feature spacious living areas, full kitchens for preparing family meals, and outdoor spaces for play and relaxation. Visitors can often find amenities like Wi-Fi and air conditioning, ensuring a comfortable stay.

The locale offers a peaceful atmosphere, and nearby attractions such as the scenic Blackwater National Wildlife Refuge provide opportunities for outdoor adventures, including hiking and wildlife observation.
Can I rent a vacation home with a pool or hot tub in Woolford?
In Woolford, Maryland, there are several vacation homes available for rent that feature pools and hot tubs. This serene area offers a mix of waterfront properties and charming homes surrounded by nature. Travelers can expect a variety of amenities, including private pools ideal for relaxation and entertainment, hot tubs for unwinding after a day of activities, and spacious outdoor areas for gatherings. Many rentals also come equipped with full kitchens, allowing guests to prepare their own meals while enjoying the beautiful surroundings.
Can I find long-stay vacation rentals in Woolford?
A long-stay vacation rental in Woolford is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Woolford?
In Woolford, travelers can find several pet-friendly house rentals that cater to those bringing their furry companions along. These vacation homes often feature spacious layouts, fully equipped kitchens, and outdoor areas, allowing pets to enjoy the fresh air alongside their owners. Many properties may include amenities such as fenced yards, which provide a safe space for pets to roam, as well as proximity to nearby parks and natural areas for walks and playtime.
Are there any remote work vacation rentals in Woolford?
In Woolford, Maryland, there are several vacation rentals that cater to remote work needs. Travelers can expect properties equipped with amenities such as free Wi-Fi and designated workspaces, making it easy to stay productive while enjoying a getaway. The serene surroundings of Woolford provide a peaceful backdrop for work, with opportunities to unwind in the evenings. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Woolford vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Woolford with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Woolford?
In Woolford, popular vacation rental amenities cater to travelers seeking comfort and convenience. Most rentals come equipped with a kitchen, allowing guests to prepare their own meals and enjoy home-cooked dining experiences. Many properties also feature a porch or lanai, providing a lovely space to relax outdoors. A deck or patio is common as well, great for enjoying the serene surroundings. Additionally, guests can expect amenities like a blender for smoothies or soups and a coffee or tea maker to start their day right.
How early should I book a Woolford vacation rental?
Book your Woolford vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Woolford, Maryland, United States of America?
In Woolford, Maryland, visitors can experience the charm of the Eastern Shore. The area is known for its picturesque landscapes and proximity to the Chesapeake Bay. Nearby, the Blackwater National Wildlife Refuge offers a chance to explore diverse wildlife and scenic trails, making it a fantastic spot for nature enthusiasts. The quaint town of Cambridge, located just a short drive away, features historic architecture, local shops, and restaurants along the waterfront, providing a charming atmosphere for a leisurely day out. For those interested in maritime history, the nearby Harriet Tubman Underground Railroad National Historical Park offers educational opportunities and insights into the region's significant past.
Can I change or cancel my Woolford home rental booking on Vrbo?
To find Woolford vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Woolford vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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