Taylors Island vacation rentals

We found 116 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Taylors Island that are perfect for your trip. Vacation rentals provide the best amenities for your family, friends, or furry companion, such as a fireplace and garden. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Taylors Island

Showing deals for:Apr 3 - Apr 10

Image gallery for New Island Home on the Chesapeake Bay Sunsets

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10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

New Island Home on the Chesapeake Bay Sunsets

Church Creek

9% off
Price is $530
$3,713 for 7 nights
All fees included
New Island Home on the Chesapeake Bay Sunsets

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Find out more about Taylors Island

Why visit Taylors Island

  • Outdoor Adventures: Enjoy a variety of outdoor activities, from hiking scenic trails to relaxing at beautiful shores.
  • Historic Lighthouses: Explore the island's charming historic lighthouses that offer stunning views and rich maritime history.
  • Family-Friendly Excursions: Discover picturesque walking paths perfect for family outings and nature exploration.
  • Cozy Accommodations: Choose from a range of inviting lodging options, including charming cottages and rustic cabins.
  • Serene Parks: Experience tranquility in local parks, ideal for picnics and enjoying the natural beauty of the area.

Popular types of accommodation in Taylors Island

If you're planning a getaway to Taylors Island, you'll find a variety of popular accommodation options to suit your needs. From cozy houses to charming cottages and rustic cabins, there's something for everyone. Plus, be sure to explore local hotels and check out amenities like parking spaces and pet policies to ensure a stress-free stay. Your perfect vacation rental awaits you in this beautiful destination.

  • Houses: The top choice for visitors in Taylors Island, offering spacious and comfortable living for families or groups.
  • Cottages: A charming and cozy option, perfect for a picturesque getaway by the water.
  • Cabins: Ideal for nature lovers, these rustic retreats provide a peaceful escape in the great outdoors.
  • Apartments: Convenient and flexible, offering a home-away-from-home experience in a compact space.
  • Villas: Luxurious accommodations that provide ample space and upscale amenities for a relaxing stay.**

Top attractions near Taylors Island

Taylors Island, Maryland, is an ideal destination for outdoor enthusiasts and adventurers. Visitors can explore historic lighthouses, picturesque islands, and serene urban parks, all while enjoying the area's stunning scenery. Whether you're seeking a beach getaway or a cultural experience, Taylors Island has a variety of attractions that cater to all types of travelers, ensuring a memorable vacation in this charming locale.

  • Calvert Cliffs State Park: A breathtaking destination featuring towering cliffs and scenic views of the Chesapeake Bay. Popular for hiking, fossil hunting, and enjoying the great outdoors, it's perfect for adventure seekers and nature lovers alike.
  • Cove Point Lighthouse: This historic lighthouse offers a glimpse into maritime history, with stunning views of the bay. Visitors can explore the surrounding area and immerse themselves in the rich cultural heritage of the region.
  • Blackwater National Wildlife Refuge: A beautiful natural reserve ideal for families and romantic getaways. The refuge is home to diverse wildlife and offers serene landscapes, perfect for birdwatching, hiking, and peaceful picnics.

Things to do recommended for couples

For a romantic getaway in Taylors Island, visit Perigeaux Vineyards and Winery for a cozy wine-tasting experience. Stroll along the Solomons Island Boardwalk, enjoying the sunset by the beach. For a bit of fun, challenge each other at R&J's PlayPark mini-golf nearby.

Things to do recommended for families

Families can unwind at Elms Beach Park, a serene recreation area located 19 miles from Taylors Island. Enjoy wellness activities and relaxation vibes, making it the perfect spot for a day of fun and togetherness in nature.

Things to do recommended for groups

Explore the unique offerings at Bay Country Shop, located 14 miles from Taylors Island, or enjoy a group shopping experience at Wildewood Shopping Center, 17 miles away. For a taste of local charm, visit Cecil's Old Mill, situated 19 miles from your base.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Taylors Island

If you're traveling with a group, as a family, bringing your pets, or planning an extended stay, it's important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Taylors Island with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options, and much more, on Vrbo.
  • Traveling to Taylors Island with young kids: Traveling with young kids can be a bit of a challenge. It's important to prioritize their comfort and safety, along with having suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Taylors Island: For many families, a trip isn't truly finished without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and pet beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Taylors Island: If you’re searching for vacation rentals with special offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Taylors Island

Taylors Island, Maryland, offers a delightful blend of outdoor adventures and stunning scenery. Visitors can explore the island's picturesque walking trails with breathtaking water views, perfect for family-friendly excursions. Nearby shores provide opportunities for relaxation and fun, while local campgrounds invite you to immerse yourself in nature. Whether you're seeking romance or a friendly atmosphere, Taylors Island and its surrounding areas promise a memorable vacation experience.

  • Cambridge: Located 14 miles from Taylors Island, Cambridge is a charming city known for its vibrant outdoor and family-friendly atmosphere. Visitors can enjoy a leisurely stroll along the scenic boardwalk, explore the recreational areas, and indulge in shopping at local centers. Notable attractions include beautiful beaches and the picturesque esplanade, making it an ideal spot for relaxation and adventure alike. Whether you’re looking to bask in the sun or engage in fun family activities, Cambridge offers a delightful experience for all.
  • Solomons: Just 13 miles away from Taylors Island, Solomons is a picturesque city that draws travelers for its stunning scenery and outdoor adventures. From recreational areas to thrilling motor racing events, there’s plenty to keep you entertained. The local landmarks, including scenic cliffs and beautiful beaches, provide breathtaking views and perfect picnic spots. If you're seeking a mix of education and excitement, don’t miss the nearby racetrack, which adds to Solomons’ unique charm.
  • Madison: Situated only 5 miles from Taylors Island, Madison is a delightful city ideal for outdoor enthusiasts and nature lovers. Enjoy leisurely walks along the boardwalk and explore the various recreational areas that showcase the area's natural beauty. With a stunning beach, a nature reserve, and a national park in close proximity, Madison offers ample opportunities for exploration and relaxation. Whether you’re hiking through lush landscapes or soaking up the sun, Madison promises an unforgettable getaway.

Best time to go to Taylors Island

If you're planning a trip to Taylors Island, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like February and November to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.5°F (2.5°C)Light RainMostly SunnyAverageSlightly Low
February39.0°F (3.9°C)Light RainMostly SunnyModerately LowSlightly Low
March45.5°F (7.5°C)Light RainMostly SunnyAverageSlightly Low
April55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
May64.8°F (18.2°C)Light RainMostly SunnyAverageAverage
June73.2°F (22.9°C)Light RainMostly SunnyModerately HighSlightly High
July78.4°F (25.8°C)Light RainMostly SunnyModerately HighSlightly High
August76.8°F (24.9°C)Light RainMostly SunnyModerately HighSlightly High
September70.9°F (21.6°C)Light RainMostly SunnyAverageAverage
October60.8°F (16.0°C)Light RainMostly SunnyAverageAverage
November49.3°F (9.6°C)Light RainMostly SunnyModerately LowAverage
December42.1°F (5.6°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Looking to cut costs on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, extending your stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash on the full booking amount. Being the organizer truly has its advantages. Enroll in our One Key rewards program to unlock exclusive savings for members and accumulate OneKeyCash on eligible stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your travels. You can create new trips, resume your previous planning, or organize your current itinerary all in one place. Your saved or booked properties will be neatly categorized as Potential, Upcoming, or Current Trips for your convenience. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Taylors Island getaway

Learn about the unique charm of Taylors Island with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. 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 Taylors Island

Do you want to discover things to do while you're in the area? Venture out of your vacation home and check out everything that makes Taylors Island a one-of-a-kind vacation spot. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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 active traveler or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Taylors Island. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Flag Ponds Nature Park (9 mi / 14.4 km)
  • Matoaka Beach (9.7 mi / 15.7 km)
  • Blackwater National Wildlife Refuge (10.2 mi / 16.4 km)
  • Long Wharf Park (14.2 mi / 22.9 km)
  • Gerry Boyle Park at Great Marsh (14.3 mi / 22.9 km)
  • Breezy Point Beach (15.6 mi / 25.2 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 center.

Frequently asked questions

What is the best area to stay in Taylors Island when booking a vacation rental?
When planning a vacation rental in Taylors Island, Maryland, one of the best areas to consider is the waterfront vicinity, particularly along the Chesapeake Bay. This region offers a serene atmosphere and stunning views, making it ideal for those looking to unwind and connect with nature. The proximity to the water provides opportunities for fishing, kayaking, and enjoying picturesque sunsets.

In this waterfront area, you can find a variety of vacation rental properties, ranging from cozy cabins to charming cottages, which cater to different tastes and group sizes. The number of available properties tends to be moderate, allowing for a selection that balances privacy with the chance to engage with fellow travelers.

Nearby attractions include the Blackwater National Wildlife Refuge, which is a must-visit for nature enthusiasts. This expansive refuge is home to diverse wildlife and offers trails for hiking, birdwatching, and photography.
How much does it cost to rent a vacation home in Taylors Island?
Prices for vacation 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 vacation 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.
Where are the best areas for renting a beach house in Taylors Island?
For renting a beach house in Taylors Island, Maryland, travelers should explore the areas along the Chesapeake Bay, particularly near the Taylors Island community itself. This region offers a selection of waterfront properties with stunning views of the bay and direct access to private beaches. Many of these rentals feature spacious outdoor decks, superb for enjoying sunsets, as well as amenities such as kayaks or paddleboards for those looking to explore the calm waters.

Additionally, the nearby Blackwater National Wildlife Refuge presents opportunities for nature enthusiasts, with vacation homes often located within a short drive of this beautiful area. These properties may offer features such as expansive backyards for family gatherings, fire pits for evening relaxation, and fully equipped kitchens to accommodate self-catering during your stay. The serene surroundings and wildlife viewing options enhance the experience for those seeking tranquility.

Moreover, travelers can take advantage of the local charm in nearby towns, where you'll find quaint shops and restaurants that showcase Maryland's coastal cuisine. Many beach rentals in this area also come with amenities like outdoor grills and picnic areas, making them ideal for summer barbecues by the water. Find your rental near the beach in Taylors Island.
What is the most popular type of vacation rental accomodation in Taylors Island?
In Taylors Island, vacation houses are the most common type of rental accommodation, with several available throughout the area. These homes typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable and home-like environment. Many of these rentals also feature outdoor spaces such as decks or patios, superb for enjoying the serene waterfront views and the natural beauty of the surrounding landscape.
Are there any family house rentals in Taylors Island?
In Taylors Island, there are several family-friendly vacation rentals available, providing a great setting for a memorable getaway. This quaint area is known for its beautiful waterfront views and tranquil atmosphere, making it ideal for families seeking relaxation and outdoor adventures. Many of the homes come with spacious living areas, equipped kitchens for convenient meal preparation, and outdoor spaces where children can play and explore.

The locale is also close to various natural attractions, including the scenic Blackwater National Wildlife Refuge, which offers opportunities for birdwatching and hiking. Families can enjoy fishing, kayaking, and other water activities in the nearby Chesapeake Bay, enhancing their stay with a blend of recreation and relaxation.
Can I find long-stay vacation rentals in Taylors Island?
A long-stay vacation rental in Taylors Island 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 Taylors Island?
In Taylors Island, there are several pet-friendly house rentals available, making it an excellent destination for travelers wanting to bring their furry companions. The area offers charming waterfront properties that often feature amenities such as private docks, spacious decks, and fully equipped kitchens, ideal for enjoying a relaxing stay. Many of these rentals come with outdoor spaces where pets can roam freely, and some even provide easy access to the water for activities like kayaking or fishing.

Taylors Island is surrounded by natural beauty, with nearby parks and wildlife areas that are great for outdoor adventures with pets. The local environment encourages exploration, whether it's walking along scenic trails or enjoying a day by the water.
Are there any remote work vacation rentals in Taylors Island?
In Taylors Island, Maryland, there are several vacation rentals that cater to remote work needs. Visitors can expect properties equipped with Wi-Fi, dedicated desk spaces, and comfortable seating arrangements, making it easy to maintain productivity while enjoying the serene surroundings. Many rentals also feature amenities like fully equipped kitchens and outdoor areas, great for relaxing after a work session. The island offers a peaceful retreat with beautiful views of the Chesapeake Bay, making it an ideal spot for those looking to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Taylors Island vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Taylors Island 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 Taylors Island?
In Taylors Island, popular vacation rental amenities include WiFi, which allows guests to stay connected during their stay. Many rentals also feature fully equipped kitchens, often with kitchen islands for added convenience, making it easy for travelers to prepare their own meals. Water views are a significant draw, as many properties are positioned to take advantage of the scenic surroundings. Additionally, some rentals come with blenders, great for whipping up refreshing smoothies or cocktails to enjoy while soaking in the beautiful coastal atmosphere.
When is the best time to visit Taylors Island for a vacation rental?
July is the most popular time to visit Taylors Island, with travelers flocking to this charming destination to enjoy the warm summer weather and vibrant outdoor activities. The peak season runs from June to August, making it ideal for those who appreciate leisurely days spent at the beach, kayaking along the picturesque waterways, or exploring the scenic landscapes that define this area.

During July, you can expect pleasant temperatures, typically ranging from the mid-70s to low 90s Fahrenheit, great for sunbathing or engaging in water sports. The island's natural beauty enhances the experience, with lush greenery and stunning sunsets providing a picturesque backdrop for relaxation and adventure alike.

For those looking for a more budget-friendly option, November offers a quieter experience. While the summer crowds have dispersed, the fall season brings its own charm, with opportunities for peaceful walks and birdwatching. The mild temperatures during this month can range from the low 40s to low 60s Fahrenheit, making it an inviting time to enjoy the tranquility of Taylors Island.

Ultimately, your choice of when to visit Taylors Island will depend on whether you prefer the lively energy of summer or the serene beauty of the fall season.
How early should I book a Taylors Island vacation rental?
Book your Taylors Island 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.
Can I change or cancel my Taylors Island home rental booking on Vrbo?
To find Taylors Island 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 Taylors Island 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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