Woolford holiday rentals

We found 147 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Woolford that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the amenities that you need and want for your stay, such as Wi-Fi and cable TV. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Woolford

Showing deals for:11 Dec - 18 Dec

Exterior
Aerial view
Aerial view
Exterior
Exceptional
(67 reviews)

Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay

Cambridge

8% off
AU$10,877
for 7 nights, 1 home
AU$1,554 per night
includes taxes & fees
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
view from balcony overlooking playhouse, pergola and Brooks Creek
Exterior
two twin beds and play area in loft
dining room
Exceptional
(276 reviews)

Family and Pet-Friendly, Waterfront with Pier

Cambridge

8% off
AU$3,148
for 7 nights, 1 cottage
AU$450 per night
includes taxes & fees
Family and Pet-Friendly, Waterfront with Pier
Interior
Living area
Outdoor dining
Dining
Exceptional
(35 reviews)

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

8% off
AU$5,093
for 7 nights, 1 home
AU$728 per night
includes taxes & fees
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Private kitchen
Outdoor dining
Dining
Living area
Exceptional
(13 reviews)

High Water Guest House<br>

Cambridge

8% off
AU$3,962
for 7 nights, 1 home
AU$566 per night
includes taxes & fees
High Water Guest House<br>
Living area
Marina
Dining
Private kitchen
Exceptional
(6 reviews)

New, Intown Waterfront Townhome wPool & Location!

Cambridge

10% off
AU$3,841
for 7 nights, 1 home
AU$549 per night
includes taxes & fees
New, Intown Waterfront Townhome wPool & Location!
Gather around the table for family dinner.
Every sunrise brings new hope for a brighter future.
Life is good!
Star light, star bright, first star I see tonight.
Exceptional
(52 reviews)

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek

8% off
AU$2,753
for 7 nights, 1 cottage
AU$393 per night
includes taxes & fees
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Foyer with stairs to second floor peak into 1st floor master bedroom
Foyer into Living Room
Kitchen/dining
Living Room into Kitchen/Dining
Exceptional
(91 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
AU$5,955
for 7 nights, 1 home
AU$851 per night
includes taxes & fees
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Boutiques and vintage shops are right outside your door
The beautiful marina is just 4 blocks away
Interior
Marina
Exceptional
(11 reviews)

Station House East: Upscale Loft in the Historic District Cambridge, MD

Cambridge

7% off
AU$1,157
for 7 nights, 1 apartment
AU$165 per night
includes taxes & fees
Station House East: Upscale Loft in the Historic District Cambridge, MD
Two bar stools are available at the kitchen bar.
The front porch has ceiling fans to help keep you cool.
Enjoy water views from the dining room and kitchen.
Front room and steps to upstairs
Exceptional
(56 reviews)

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly

Fishing Creek

7% off
AU$1,877
for 7 nights, 1 home
AU$268 per night
includes taxes & fees
Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly
Property grounds
Marina
Living area
Marina
Exceptional
(13 reviews)

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Cambridge

8% off
AU$2,220
for 7 nights, 1 apartment
AU$317 per night
includes taxes & fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Exterior
Exterior
Dining
Private kitchen
Exceptional
(28 reviews)

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

Cambridge

8% off
AU$6,566
for 7 nights, 1 home
AU$938 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Woolford getaway

Learn about the unique charm of Woolford with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway 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 looking for attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Woolford a fun spot to go on holiday. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

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

Exploring the natural landscape of Woolford

Whether you're an adventurous traveller or just want to appreciate the scenery, Woolford is a great spot to appreciate mother nature. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Cove Point Beach (13.9 mi / 22.3 km)
  • Flag Ponds Nature Park (15.6 mi / 25.1 km)
  • Matoaka Beach (16.2 mi / 26 km)

Transport 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 centre.

Frequently asked questions

What is the best area to stay in Woolford when booking a holiday rental?
When considering a holiday rental in Woolford, Maryland, the surrounding area of Cambridge is an excellent choice. This charming town, located just a short drive from Woolford, offers a delightful blend of historical charm and natural beauty. One of the top attractions in Cambridge is the Harriet Tubman Museum and Educational Centre, which provides a profound insight into the life of the famed abolitionist and her connection to the local area. Additionally, the nearby Blackwater National Wildlife Refuge is a must-visit for nature enthusiasts, offering picturesque landscapes and opportunities for birdwatching.In terms of holiday rentals, Cambridge boasts a variety of properties, ranging from quaint waterfront cottages to more spacious family homes, suiting different preferences and group sizes. Staying in Cambridge not only provides convenient access to Woolford but also allows visitors to explore the rich history and stunning scenery that the region has to offer.
Where are the best areas for renting a beach house in Woolford?
For renting a beach house in Woolford, consider the beautiful surroundings of the nearby Chesapeake Bay. The area offers an array of waterfront properties, particularly along the shoreline near the small community of Woolford. Many of these beach houses feature stunning views of the bay and come equipped with amenities such as private docks, outdoor terraces, and spacious living areas, great for families or groups looking to enjoy a seaside retreat.Additionally, nearby towns like Cambridge and Easton provide more options, with charming beach rentals that often include modern kitchens, barbecuing facilities, and access to sandy beaches. These properties typically have a relaxed coastal vibe, with features like large decks for entertaining and outdoor showers for rinsing off after a day at the beach.Exploring further, the nearby Blackwater National Wildlife Refuge offers opportunities for outdoor activities such as hiking and birdwatching, making it an excellent complement to a beach getaway. Rentals in this region often provide a blend of tranquillity and adventure, ensuring guests can enjoy both the natural beauty of the bay and the vibrant local culture.
What is the most popular type of holiday rental accomodation in Woolford?
In Woolford, holiday houses are the predominant type of holiday rental, with around 15 available throughout the area. These properties typically offer a spacious and comfortable environment, featuring multiple bedrooms, fully equipped kitchens, and ample living space for relaxation. Many holiday houses also include outdoor areas, such as gardens or patios, where guests can enjoy the serene surroundings.
Are there any family house rentals in Woolford?
In Woolford, Maryland, there are several family-friendly house rentals available, making it an excellent choice for families seeking a getaway. The area is known for its picturesque landscapes and proximity to the Chesapeake Bay, offering opportunities for outdoor activities. Many of these homes come equipped with spacious family rooms, fully functional kitchens for preparing meals together, and outdoor areas where children can play safely.Visitors can also enjoy local attractions such as the nearby Blackwater National Wildlife Refuge, which is superb for nature walks and spotting wildlife. Additionally, the charm of the local community and its rich maritime history provides a wonderful backdrop for family exploration.
Can I rent a holiday home with a pool or hot tub in Woolford?
In Woolford, Maryland, there are several holiday homes available for rent that feature pools and hot tubs, providing a fantastic option for travellers looking to relax and unwind. The area is known for its serene landscapes and proximity to the Chesapeake Bay, making it an ideal getaway for those seeking a peaceful retreat.Many of these holiday rentals come equipped with private pools, inviting hot tubs, and spacious outdoor areas superb for gatherings or family fun. Inside, you can typically expect amenities such as fully equipped kitchens, comfortable living spaces, and modern conveniences like Wi-Fi and air conditioning.
Are there pet-friendly house rentals in Woolford?
In Woolford, there are several pet-friendly house rentals available, making it an excellent choice for travellers looking to enjoy a getaway with their furry friends. Many of these properties come equipped with amenities such as spacious backyards, outdoor seating areas, and fully equipped kitchens, providing a comfortable and convenient stay for families or groups.The area itself offers a tranquil environment, great for leisurely walks with pets, and you can expect easy access to local parks where you can enjoy nature. While Woolford is a quiet spot, its proximity to the beautiful Chesapeake Bay allows for various outdoor activities, including kayaking and fishing, which can be enjoyable for pets and their owners alike.
Are there any remote work holiday rentals in Woolford?
In Woolford, Maryland, there are around 15 holiday rentals suitable for remote work. These properties typically offer essential amenities such as free Wi-Fi, allowing for seamless connectivity while working from a comfortable setting. Many rentals also feature dedicated workspaces or desks, providing a quiet area for productivity.The area itself is charming, surrounded by natural beauty, superb for taking breaks outdoors. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Woolford?
In Woolford, popular rental amenities include kitchens, which allow guests to prepare their own meals, as well as porches or lanais that provide a comfortable outdoor space to relax. Many properties also feature decks or patios, great for enjoying the serene surroundings. Additional amenities often include coffee and tea makers for a convenient start to the day, and blenders for making smoothies or other beverages.
What are the top attractions in Woolford?
Woolford, Maryland, is a small and serene community that offers a glimpse into the beauty of the Eastern Shore. One of the main attractions in the area is the nearby Blackwater National Wildlife Refuge, which provides opportunities for birdwatching, hiking, and exploring the diverse local flora and fauna. The refuge is particularly famous for its waterfowl and other wildlife, making it a superb spot for nature enthusiasts.Additionally, the picturesque towns of Cambridge and Easton are just a short drive away, where visitors can enjoy charming shops, art galleries, and waterfront dining. The Choptank River is also nearby, offering various recreational activities such as fishing, kayaking, and scenic boat tours.For those interested in history, the area features several historical sites, including the Harriet Tubman Underground Railroad Visitor Centre, which commemorates the life and legacy of the famed abolitionist.
Are all fees included in the Woolford holiday homes prices shown on Stayz?
Stayz 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.
Are there any Woolford holiday homes with parking?
Stayz offers a wide selection of holiday homes in Woolford with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Woolford holiday homes?
You can find great discounts on holiday homes in Woolford on Stayz, 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.
Can I change or cancel my Woolford holiday home booking on Stayz?
To find Woolford holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Woolford?
A long-stay holiday home in Woolford is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Woolford holiday home?
Book your Woolford holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Woolford?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Woolford to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.