Taylors Island holiday lettings

We found 115 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Taylors Island that are perfect for your trip. Holiday rentals offer the amenities that you expect for your family, friends or furry companion, such as air conditioning and cable TV. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Taylors Island

Showing deals for:5 Jun - 12 Jun

Image gallery for 5 bedroom, 8 bed, 3 story house a block from beach

Terrace/patio
9.6 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)

5 bedroom, 8 bed, 3 story house a block from beach

Saint Leonard

5% off
Price is £2,174
for 7 nights, 1 home
£311 per night
includes taxes & fees
5 bedroom, 8 bed, 3 story house a block from beach

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Find the perfect holiday rental for your Taylors Island getaway

Learn about the unique charm of Taylors Island 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 Taylors Island

Are you looking for top things to see and do while you're in the area? Venture out of your cosy holiday rental and check out everything that Taylors Island has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Perigeaux Vineyards and Winery (11.8 mi / 19 km)
  • Phillips Wharf Environmental Center (17.2 mi / 27.6 km)
  • Chesapeake Hills Golf Course (9.2 mi / 14.8 km)
  • Bay Country Shop (14.3 mi / 23.1 km)

Exploring the natural landscape of Taylors Island

Whether you're an outdoor enthusiast or just want to take in the scenery, Taylors Island is a great spot to appreciate mother nature. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Matoaka Beach (9.7 mi / 15.7 km)
  • Blackwater National Wildlife Refuge (10.2 mi / 16.4 km)
  • Annmarie Sculpture Garden and Arts Center (12 mi / 19.3 km)
  • Drum Point Lake (12.1 mi / 19.4 km)
  • Long Wharf Park (14.2 mi / 22.9 km)
  • Gerry Boyle Park at Great Marsh (14.3 mi / 22.9 km)

How to get to and around Taylors Island

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 26.8 mi (43.2 km) from the city centre.

Frequently asked questions

What is the best area to stay in Taylors Island when booking a holiday rental?
When considering a holiday rental in Taylors Island, Maryland, the best area to stay is typically around the waterfront locations. This charming area offers a peaceful retreat with stunning views of the Chesapeake Bay. One of the top attractions nearby is the Blackwater National Wildlife Refuge, which is a haven for birdwatchers and nature enthusiasts, providing an opportunity to explore its extensive trails and observe a variety of wildlife.

Another point of interest is the local marinas, where you can enjoy activities such as kayaking or fishing, making it an ideal spot for those who appreciate outdoor adventures. The area boasts a limited number of properties, ensuring a more intimate and tranquil experience, allowing visitors to fully immerse themselves in the serene beauty of this picturesque island.
How much does it cost to rent a holiday home in Taylors Island?
Prices for holiday rentals in Taylors Island 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 Taylors Island 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 Taylors Island holiday house rentals?
You can find great discounts on house rentals in Taylors Island 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.
What is the most popular type of holiday rental accomodation in Taylors Island?
In Taylors Island, holiday houses are the predominant type of holiday rental, with around 12 available across the area. These properties typically offer spacious living environments, multiple bedrooms, fully equipped kitchens, and outdoor spaces where guests can relax and enjoy the surrounding natural beauty. Ideal for families or groups, these holiday houses provide a comfortable and homely atmosphere, making them a popular choice for visitors looking to explore the scenic landscapes of Maryland.
Are there any family house rentals in Taylors Island?
In Taylors Island, Maryland, there are several family-friendly house rentals available, making it an excellent choice for those looking to escape for a while. The area is known for its picturesque coastal views and serene atmosphere, superb for families seeking relaxation and outdoor activities. Many of these homes come equipped with spacious living areas, full kitchens, and outdoor decks, where families can enjoy meals together or simply take in the views.

Visitors can explore the nearby waterways, which are great for kayaking, fishing, or simply enjoying a day out on the water. The surrounding natural beauty provides ample opportunities for nature walks and birdwatching, making it a fantastic destination for families who appreciate the outdoors.
Can I find long-stay holiday rentals in Taylors Island?
A long-stay holiday rental in Taylors Island 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Taylors Island?
In Taylors Island, there are several pet-friendly house rentals available, making it a delightful destination for travellers looking to bring their furry companions along. Many of these holiday homes offer amenities such as spacious yards, outdoor seating areas, and fully equipped kitchens, ensuring a comfortable stay for both humans and pets.

The area is known for its peaceful setting and proximity to the Chesapeake Bay, where pets can enjoy walks along the water's edge. Nearby, the Blackwater National Wildlife Refuge offers a range of outdoor activities, including hiking trails that welcome pets on leashes, providing opportunities for memorable adventures.
Are there any remote work holiday rentals in Taylors Island?
In Taylors Island, Maryland, there are several remote work-friendly holiday rentals available, with around 12 options to choose from. This serene island setting offers a peaceful environment for those looking to balance work and leisure. Many of the properties provide essential amenities such as free Wi-Fi, allowing for a seamless remote working experience.

The rentals typically feature comfortable workspaces, spacious living areas, and full kitchens, making it easy to prepare meals during your stay. Given the tranquil surroundings, you can also enjoy some downtime by exploring the natural beauty of the island, including local wildlife and picturesque waterfront views. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Taylors Island holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Taylors Island 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 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 Taylors Island?
In Taylors Island, popular rental amenities include kitchens, which allow guests to prepare their own meals, and coffee and tea makers for a comforting start to the day. Many properties also feature blenders, superb for whipping up smoothies or other beverages. For those cooler evenings, fireplaces provide a warm and inviting atmosphere. Additionally, the presence of paper towels adds a practical touch, making clean-up easier after meals or activities.
When is the best time to visit Taylors Island for a holiday rental?
The peak season for holiday rentals on Taylors Island is during the summer months, specifically from June to August. This vibrant period attracts families and outdoor enthusiasts eager to enjoy the beautiful Chesapeake Bay, where activities such as kayaking, fishing, and crabbing abound. July stands out as the most popular month, offering warm temperatures and a lively option great for beach outings and water sports.

During the summer, visitors can expect comfortable highs averaging around 28 to 32 degrees Celsius, making it ideal for enjoying the island's natural beauty and engaging in outdoor adventures. The pleasant weather also sets the stage for romantic sunset strolls along the shore or picnics in the scenic parks.

For those seeking a more budget-friendly experience, consider visiting in November. This month provides a quieter atmosphere, allowing you to explore the island's charm and tranquillity at a more leisurely pace. The cooler temperatures, ranging from 5 to 15 degrees Celsius, make it a wonderful time for peaceful walks and enjoying the local wildlife.

Ultimately, the best time to visit Taylors Island depends on whether you prefer the lively summer scene filled with activities or the serene, off-peak experience that November offers.
How early should I book a Taylors Island holiday rental?
Book your Taylors Island holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Taylors Island?
In Taylors Island, visitors can enjoy a tranquil escape with natural beauty and unique attractions. The nearby Blackwater National Wildlife Refuge is a significant highlight, offering stunning landscapes, walking trails, and opportunities for birdwatching and wildlife photography. This area is home to a diverse range of species, making it superb for nature enthusiasts.

The local community also showcases its maritime heritage, with the Taylors Island Church and the surrounding waterfront areas reflecting the charm of this small fishing village. For those interested in history, the nearby town of Cambridge offers additional attractions, including the Harriet Tubman Museum and Educational Centre, which celebrates the life and legacy of the famous abolitionist.

The area's quiet waters are ideal for kayaking and fishing, providing a serene environment for outdoor activities.
Can I change or cancel my Taylors Island home rental booking on Vrbo?
To find Taylors Island holiday 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 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 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, Vrbo 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 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 Taylors Island holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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