Taylors Island vacation rentals

We found 121 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 11 - Dec 18

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

Family and Pet-Friendly, Waterfront with Pier

Cambridge

9% off
$295
$2,063 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
$1,082
$7,571 for 7 nights
All fees included
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
Exterior
Dining
Living area
Terrace/patio
Exceptional
(5 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
$461
$3,229 for 7 nights
All fees included
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Living area
Outdoor dining
Interior
Living area
Exceptional
(5 reviews)

Driftwood Haven, Chesapeake Bay views throughout

Lusby

13% off
$429
$3,002 for 7 nights
All fees included
Driftwood Haven, Chesapeake Bay views throughout
Outdoor dining
Living area
Dining
Private kitchen
Exceptional
(35 reviews)

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

9% off
$501
$3,507 for 7 nights
All fees included
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
steps to the loft
entryway
Exterior
loft bedroom
Exceptional
(61 reviews)

Soul Oasis - home on the Chesapeake Bay

Lusby

8% off
$178
$1,245 for 7 nights
All fees included
Soul Oasis - home on the Chesapeake Bay
Exterior
Outdoor dining
Exterior detail
Outdoor dining
Exceptional
(174 reviews)

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

St. Leonard

6% off
$202
$1,416 for 7 nights
All fees included
Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
Kitchen with peak into living room
Foyer into Living Room
Kitchen/dining
Foyer with stairs to second floor peak into 1st  floor master bedroom
Exceptional
(91 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
$601
$4,207 for 7 nights
All fees included
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
View of parking pad 1 car is  backed in and 1 for studio on the bay pulled in.
Living area
Private kitchen
Exterior detail
Exceptional
(31 reviews)

Studio on the Bay.

St. Leonard

8% off
$166
$1,162 for 7 nights
All fees included
Studio on the Bay.
Private kitchen
Exterior
Exterior
Living area
Exceptional
(28 reviews)

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

Cambridge

9% off
$664
$4,649 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 is the most popular type of vacation rental accommodation in Taylors Island?
Based on our research, lodges are considered the most popular type of vacation rental in Taylors Island. But as you know, everyone's idea of an epic stay differs. Vrbo has vacation homes of all shapes, sizes and budgets, and we'll help you to find your perfect match.
How much does it cost to rent a vacation rental in Taylors Island?
The average price for a vacation home in Taylors Island depends on several factors, such as season, property type and length of stay. Whether you're searching for a sprawling villa with room to move around or an apartment for just you and the kids, just add your dates of travel to find stays with great value.
How much does it cost to rent a beach house in Taylors Island?
Prices for beach houses in Taylors Island can vary depending on the type and size of the property and when you're traveling. All you have to do is enter your travel dates into Vrbo and the number of guests to view your rental options and prices. From there you can use our filters to narrow down your search by ratings, nearby activities, amenities and more.
What are popular rental amenities in Taylors Island?
Some of the most popular rental amenities people are looking for in Taylors Island include a fireplace, a nearby waterfront and a water view. Whether you're hitting the road with family, buddies or even pets, Vrbo vacation properties come with the best amenities for making epic memories with the people who matter most.
Are there vacation rentals with WiFi in Taylors Island?
Whether you'd like to stay in touch with world events, reply to emails or update your social media, there are four vacation homes with WiFi in Taylors Island. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How old do you have to be to rent a vacation rental in Taylors Island?
The minimum age permitted can vary across properties on Vrbo, so be sure to check the rules of the vacation home in Taylors Island you're interested in. But usually, it's 16, 18 or 21.
How long can I rent a vacation rental in Taylors Island for?
It all depends on the Taylors Island property. To look at a list of options offering extended stays, just type your travel dates and guest number into Vrbo. You can enjoy having the property to yourself, as well as comforts such as a fully-equipped kitchen and outdoor spaces to run around in. Be on the lookout for any long-term stays that offer weekly or monthly discounts.
Does Vrbo offer discounts for vacation homes in Taylors Island?
On Vrbo, we've got some incredible bargains and discounts for Taylors Island. Take a look at our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're after a mini getaway or a much longer stay, Vrbo has options for all budgets and styles.

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