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:7 Nov - 14 Nov

Image gallery for New Island Home on the Chesapeake Bay Sunsets

Exterior
10 out of 10 rating
Exceptional
(7 reviews)

New Island Home on the Chesapeake Bay Sunsets

Church Creek, MD

8% off
Price is £3,081
£440 per night
includes taxes & fees
New Island Home on the Chesapeake Bay Sunsets

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

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    More space, more privacy, more amenities — more value

Find out more about Taylors Island

Find out more about Taylors Island

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)
  • Chesapeake Hills Golf Course (9.2 mi / 14.8 km)
  • Bay Country Shop (14.3 mi / 23.1 km)
  • Phillips Wharf Environmental Center (17.2 mi / 27.6 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)
  • Long Wharf Park (14.2 mi / 22.9 km)
  • Gerry Boyle Park at Great Marsh (14.3 mi / 22.9 km)
  • Middle Hooper Island (14.5 mi / 23.4 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 planning a holiday rental in Taylors Island, Maryland, one of the most appealing areas to consider is the vicinity around the waterfront. This charming locale offers a serene atmosphere with stunning views of the Choptank River and is great for those who appreciate nature and outdoor activities. The area features a modest selection of properties, which means you can enjoy a more intimate and tranquil getaway.

Staying near the waterfront places you close to some delightful attractions. One such highlight is the Taylors Island Wildlife Management Area, where you can immerse yourself in the local ecosystem, great for birdwatching enthusiasts and those who enjoy hiking along scenic trails. Additionally, the nearby Blackwater National Wildlife Refuge is a short drive away and offers expansive landscapes filled with wildlife, making it an ideal spot for nature lovers.
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 most popular type of rental accommodation, with several available in the area. These properties typically provide spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking to enjoy a relaxing getaway. Many of these holiday houses also feature outdoor spaces, such as decks or gardens, where guests can unwind and take in the natural beauty of the surroundings.
Are there any family house rentals in Taylors Island?
In Taylors Island, Maryland, there are several family-friendly house rentals available, making it a lovely spot for a family getaway. The area is known for its serene environment and proximity to the Chesapeake Bay, offering opportunities for fishing, boating, and enjoying nature.

Many of these homes feature spacious living areas, full kitchens equipped for cooking family meals, and outdoor spaces where children can play or families can gather for barbecues. Visitors can expect amenities like Wi-Fi, air conditioning, and sometimes even private docks for easy access to the water.
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, travellers can find several pet-friendly house rentals that cater to those looking to enjoy a relaxing getaway with their furry companions. Many of these rentals offer amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups.
Are there any remote work holiday rentals in Taylors Island?
In Taylors Island, Maryland, there are several holiday rentals available that cater to remote work needs. Travellers can expect properties equipped with essential amenities such as Wi-Fi, dedicated desk spaces, and comfortable chairs, allowing for a productive work environment. The serene surroundings of the island provide a tranquil backdrop, ideal for focusing on work while also enjoying the beauty of nature. Nearby points of interest, including picturesque waterfronts and local parks, offer opportunities for relaxation during breaks. 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 holiday rental amenities include complimentary in-room Wi-Fi, ensuring guests stay connected during their stay. Many properties also offer third-party internet services for greater connectivity. Onsite parking is available, which is particularly convenient for those travelling by car. Additionally, rentals often feature essential kitchen appliances such as blenders and coffee makers, allowing visitors to prepare meals and enjoy their morning coffee with ease.
When is the best time to visit Taylors Island for a holiday rental?
The most popular time to visit Taylors Island is during the peak season from June to August. This lively period attracts families and outdoor enthusiasts keen to enjoy the stunning natural beauty of the area, including its picturesque waterways and abundant wildlife. With warm temperatures often reaching the low 30s Celsius, visitors can partake in a variety of activities such as fishing, kayaking, and exploring the local wildlife refuges.

July stands out as the busiest month, offering vibrant community events and festivals that celebrate the region's rich heritage. The warm weather creates a friendly space for beach days, picnics, and leisurely walks along the shoreline, making it an excellent choice for those looking to soak up the sun.

For travellers seeking a more budget-friendly option, consider visiting Taylors Island in November. Although this is outside the peak season, the tranquility of the landscape during this time allows for peaceful exploration of the area's natural beauty. The crisp autumn air and stunning fall foliage provide a lovely backdrop for outdoor activities like hiking and birdwatching, all while enjoying a quieter experience.
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.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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