Taylors Island vacation rentals

We found 125 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:Dec 4 - Dec 11

dining room
Exterior
Outdoor banquet area
view from balcony overlooking playhouse, pergola and Brooks Creek
Exceptional
(275 reviews)

Family and Pet-Friendly, Waterfront with Pier

Cambridge

9% off
$299
$2,094 for 7 nights
All fees included
Family and Pet-Friendly, Waterfront with Pier
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
$1,102
$7,716 for 7 nights
All fees included
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
Exterior
Dining
Game room
Terrace/patio
Exceptional
(5 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
$465
$3,257 for 7 nights
All fees included
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Living area
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
Private kitchen
Living area
Dining
Interior
Exceptional
(35 reviews)

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

9% off
$510
$3,573 for 7 nights
All fees included
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Exterior
Outdoor dining
Exterior detail
Outdoor dining
Exceptional
(173 reviews)

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

St. Leonard

6% off
$204
$1,430 for 7 nights
All fees included
Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
Kitchen/dining
Foyer into Living Room
Living Room into Kitchen/Dining
Foyer with stairs to second floor peak into 1st floor master bedroom
Exceptional
(90 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
$600
$4,203 for 7 nights
All fees included
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Private kitchen
Living area
View of parking pad 1 car is backed in and 1 for studio on the bay pulled in.
Exterior detail
Exceptional
(31 reviews)

Studio on the Bay.

St. Leonard

8% off
$164
$1,148 for 7 nights
All fees included
Studio on the Bay.
Dining
Exterior
Private kitchen
Living area
Exceptional
(28 reviews)

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

Cambridge

8% off
$666
$4,663 for 7 nights
All fees included
Spacious waterfront home with amazing views, private pier, fishing and crabbing.

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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.

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)
  • 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 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

What are the best areas to stay in a vacation rental in Taylors Island?
When looking for the best areas to stay in a vacation rental in Taylors Island, you'll find a selection of houses across the island. These properties offer whole-home privacy and ample space, making them ideal for families, groups, or anyone seeking a quiet retreat. All vacation rentals in Taylors Island are suitable for large groups, and a selection of luxury and budget-friendly options are available, ensuring a comfortable stay for various preferences.
What are the most popular vacation rentals in Taylors Island?
Houses are the most popular choice for vacation rentals in Taylors Island, making up the majority of available properties. These homes are favored by guests seeking whole-home privacy, more space, and room to settle in comfortably. They are particularly well-suited for families and groups, offering multiple bedrooms and living areas for shared experiences.
What amenities do vacation rentals in Taylors Island usually offer?
Vacation rentals in Taylors Island come equipped with essential amenities for a comfortable stay. You can expect fully equipped kitchens, free Wi-Fi, and convenient parking at all properties. Many rentals also provide air conditioning, a washer, and outdoor spaces like balconies or terraces. A selection of properties also features private outdoor pools, adding an extra touch of relaxation to your visit.
Are there family-friendly vacation rentals in Taylors Island?
Families will find a selection of family-friendly vacation rentals in Taylors Island, mostly houses. These properties are designed to accommodate all ages, often including amenities like fully equipped kitchens for meal preparation, laundry facilities, and separate living areas for relaxation. Some rentals also offer games for children and outdoor play areas, ensuring entertainment for younger guests.
Are there pet-friendly vacation rentals in Taylors Island?
Bringing your furry friends to Taylors Island is easy, with several pet-friendly vacation rentals available. These properties are primarily houses that welcome dogs, providing a comfortable setting for your entire family. They are set up to accommodate pets, allowing you to enjoy your vacation without leaving your companions behind.
What are the best areas for group vacation rentals in Taylors Island?
For groups planning a getaway, all vacation rentals in Taylors Island are well-suited, primarily consisting of houses. These properties offer ample space with multiple bedrooms and bathrooms, large dining areas, and fully equipped kitchens, making them ideal for shared meals and gatherings. Many also provide convenient parking and outdoor spaces like balconies or terraces, perfect for enjoying time together.
What are the best luxury vacation rentals in Taylors Island?
Guests seeking an upscale experience will find a selection of luxury vacation rentals in Taylors Island, predominantly houses. These properties often feature premium amenities such as fireplaces, private outdoor spaces like balconies or terraces, and sometimes even a private outdoor pool. Many also offer access to fitness facilities and spa services, ensuring a comfortable and indulgent stay.
Are there any budget-friendly vacation rentals in Taylors Island?
You can find a few budget-friendly vacation rentals in Taylors Island, primarily houses, that offer great value for your trip. These properties provide essential amenities like fully equipped kitchens, which can help save on dining expenses, and free Wi-Fi. Many also include laundry facilities and convenient parking, making them practical and cost-effective for various trip types.
Are there any vacation rentals in Taylors Island with a pool?
Yes, you can find a vacation rental in Taylors Island that features a pool, specifically a house. This property offers a private outdoor pool, providing a refreshing option for relaxation and privacy during your stay.
Are there any family-friendly vacation rentals in Taylors Island with a pool?
Yes, you can find a family-friendly vacation rental in Taylors Island that includes a pool. This house offers a private outdoor pool, along with family-focused amenities like a fully equipped kitchen, laundry facilities, and games for children, ensuring a fun and comfortable stay for everyone.
Are there any short-term vacation rentals in Taylors Island for a weekend getaway?
Planning a weekend getaway to Taylors Island is straightforward, with a selection of houses available for short-term stays. These properties offer whole-home privacy and are a short drive from local attractions like Ragged Island, which is about 3 miles from typical rental areas. They provide a comfortable and convenient base to explore the area for a two- or three-night trip.
Are there any remote work vacation rentals in Taylors Island?
For those looking to combine work and leisure, all vacation rentals in Taylors Island are well-equipped for remote work and extended stays. These properties, primarily houses, come with essential amenities like high-speed Wi-Fi, fully equipped kitchens, and laundry facilities, making them convenient for longer periods. They offer a comfortable and private setting for productivity away from the office.
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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