Taylors Island vacation rentals

We found 123 vacation rentals — enter your dates for availability

Immerse yourself in the enchanting charm of Taylors Island, where tranquil waters meet lush landscapes and historic lighthouses stand as guardians of maritime tales. With a wealth of outdoor adventures from hiking to birding, and family-friendly spots like the Island Family Campground, it’s perfect for groups seeking both relaxation and excitement. Choose from cozy cottages or rustic cabins, and enjoy the comfort and convenience of a vacation rental, where you can create lasting memories together in a home-like setting.

Holiday rentals with weekly discounts - Taylors Island

Showing deals for:Nov 6 - Nov 13

Exterior
Terrace/patio
Dining
Interior
Exceptional
(8 reviews)

New Island Home on the Chesapeake Bay Sunsets

Church Creek

9% off
$690
$4,833 for 7 nights
All fees included
New Island Home on the Chesapeake Bay Sunsets
Kitchen/dining
Foyer into Living Room
Foyer with stairs to second floor peak into 1st floor master bedroom
Living Room into Kitchen/Dining
Exceptional
(90 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
$603
$4,224 for 7 nights
All fees included
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Exterior
Dining
Game room
Living area
Exceptional
(5 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
$609
$4,260 for 7 nights
All fees included
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Interior
Outdoor dining
Living area
Interior
Exceptional
(5 reviews)

Driftwood Haven, Chesapeake Bay views throughout

Lusby

13% off
$437
$3,056 for 7 nights
All fees included
Driftwood Haven, Chesapeake Bay views throughout
Living area
Exterior
Interior
Private kitchen
Exceptional
(64 reviews)

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

Cambridge

8% off
$1,102
$7,713 for 7 nights
All fees included
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
loft bedroom
entryway
steps to the loft
dining area
Exceptional
(55 reviews)

Soul Oasis - home on the Chesapeake Bay

Lusby

8% off
$178
$1,248 for 7 nights
All fees included
Soul Oasis - home on the Chesapeake Bay
Exterior
Private kitchen
Living area
Game room
Exceptional
(19 reviews)

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

St. Leonard

5% off
$460
$3,219 for 7 nights
All fees included
5 bedroom, 8 bed, 3 story house a block from beach
Game table to enjoy the board games, backgammon, chess, cards and more
Sunroom faces the water.
Living area
Great kitchen for entertaining and gathering
Exceptional
(32 reviews)

Stunning Water Front Home with Private Dock and Beach and Sunsets

Lusby

8% off
$466
$3,259 for 7 nights
All fees included
Stunning Water Front Home with Private Dock and Beach and Sunsets
Exterior
Exterior
Private kitchen
Dining
Exceptional
(27 reviews)

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

Cambridge

8% off
$668
$4,679 for 7 nights
All fees included
Spacious waterfront home with amazing views, private pier, fishing and crabbing.

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

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.

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)
  • Bay Country Shop (14.3 mi / 23.1 km)
  • Phillips Wharf Environmental Center (17.2 mi / 27.6 km)
  • Chesapeake Hills Golf Course (9.2 mi / 14.8 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:

  • Cove Point Beach (7.7 mi / 12.4 km)
  • 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)

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

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.
What is the most popular type of vacation rental accomodation in Taylors Island?
In Taylors Island, vacation houses are the most popular type of rental accommodation, with several available throughout the area. These homes typically offer a spacious and comfortable setting, featuring multiple bedrooms, fully equipped kitchens, and cozy living areas. Many also come with outdoor spaces such as decks or patios, allowing guests to enjoy the serene surroundings and waterfront views.
Are there any family house rentals in Taylors Island?
In Taylors Island, Maryland, there are several family-friendly house rentals available, making it a wonderful destination for families looking to enjoy a quiet getaway. Many of these homes provide spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces for children to play and families to gather. Visitors will often find amenities like Wi-Fi and air conditioning to ensure a comfortable stay.The area is known for its serene waterfront views and proximity to nature, with opportunities for fishing, crabbing, and exploring the local wildlife. Families can also take advantage of nearby parks and recreational activities, enhancing their experience in this picturesque locale.
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, travelers will find several pet-friendly house rentals that cater to those looking to bring their furry companions along. Many of these homes are situated near the waterfront, offering picturesque views and easy access to outdoor activities. Expect amenities such as spacious living areas, fully equipped kitchens, and outdoor decks or patios, ideal for enjoying the serene surroundings.The area provides a tranquil setting for pet owners, with opportunities for walks along the shore and exploration of the natural beauty of the Chesapeake Bay. Additionally, the nearby Blackwater National Wildlife Refuge is a great spot for hiking and wildlife watching, allowing pets to enjoy the outdoors alongside their owners.
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. These properties typically offer amenities such as dedicated workspaces, including desks and comfortable chairs, ensuring a productive environment. High-speed Wi-Fi is commonly available, allowing for reliable internet access necessary for remote work.Travelers can enjoy the serene surroundings of Taylors Island, which provides a peaceful backdrop for both work and relaxation. The area is also close to scenic waterfront views and nature trails, making it a great choice for those looking to balance work with outdoor activities. 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 cater to travelers seeking comfort and convenience. Many rentals feature fully equipped kitchens, allowing guests to prepare their own meals during their stay. Additional amenities often include blenders for smoothies or drinks, coffee and tea makers for morning routines, and cozy fireplaces that create a warm atmosphere, especially during cooler months. Guests can also expect essential items like paper towels for added convenience.
When is the best time to visit Taylors Island for a vacation rental?
The best time to visit Taylors Island for a vacation rental is during the peak season of June through August, with July being the most popular month. This vibrant period attracts travelers eager to enjoy the warm weather and the abundant outdoor activities available, from kayaking in the Chesapeake Bay to exploring the island's scenic landscapes.During the summer months, temperatures typically range from the mid-70s to the low 90s Fahrenheit, providing a comfortable climate for beach outings and sightseeing. Visitors can take part in the natural beauty of Taylors Island, taking advantage of the picturesque waterfront views and engaging in local fishing or crabbing adventures.For those seeking a more budget-friendly option, consider planning your visit in November. This quieter month offers a unique opportunity to experience the island's charm without the crowds, allowing for peaceful walks along the shore and a chance to savor local cuisine in a more relaxed setting.
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.
What are the top attractions in Taylors Island, Maryland, United States of America?
In Taylors Island, visitors can enjoy a serene coastal atmosphere and explore the natural beauty of the area. One of the top attractions is the Taylors Island Marsh, which offers opportunities for birdwatching and photography among its scenic wetlands. The nearby Blackwater National Wildlife Refuge, located a short drive away, is a must-visit for nature enthusiasts, providing trails and viewing platforms to observe diverse wildlife.Additionally, the local waterfront offers access to various water activities such as kayaking and fishing, allowing guests to fully experience the Chesapeake Bay's charm.
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.

More Vacation Ideas