Taylors Island holiday homes

We found 121 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other 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:11 Dec - 18 Dec

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
NZ$14,001
for 7 nights, 1 home
NZ$2,000 per night
includes taxes & fees
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
Exterior
Dining
Terrace/patio
Games room
Exceptional
(5 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
NZ$5,896
for 7 nights, 1 home
NZ$842 per night
includes taxes & fees
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Private kitchen
Living area
Outdoor dining
Interior
Exceptional
(35 reviews)

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

8% off
NZ$6,389
for 7 nights, 1 home
NZ$913 per night
includes taxes & fees
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
dining room
Exterior
Outdoor banquet area
view from balcony overlooking playhouse, pergola and Brooks Creek
Exceptional
(276 reviews)

Family and Pet-Friendly, Waterfront with Pier

Cambridge

8% off
NZ$3,902
for 7 nights, 1 cottage
NZ$557 per night
includes taxes & fees
Family and Pet-Friendly, Waterfront with Pier
Living area
Outdoor dining
Living area
Interior
Exceptional
(5 reviews)

Driftwood Haven, Chesapeake Bay views throughout

Lusby

12% off
NZ$5,525
for 7 nights, 1 home
NZ$789 per night
includes taxes & fees
Driftwood Haven, Chesapeake Bay views throughout
loft bedroom
entryway
Exterior
dining area
Exceptional
(61 reviews)

Soul Oasis - home on the Chesapeake Bay

Lusby

8% off
NZ$2,236
for 7 nights, 1 cottage
NZ$319 per night
includes taxes & fees
Soul Oasis - home on the Chesapeake Bay
Kitchen with peak into living room
Foyer into Living Room
Living Room into 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
NZ$7,443
for 7 nights, 1 home
NZ$1,063 per night
includes taxes & fees
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Exterior
Outdoor dining
Exterior detail
Outdoor dining
Exceptional
(174 reviews)

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

St. Leonard

6% off
NZ$2,507
for 7 nights, 1 cottage
NZ$358 per night
includes taxes & fees
Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
View of parking pad 1 car is backed in and 1 for studio on the bay pulled in.
Living area
Private kitchen
Room
Exceptional
(31 reviews)

Studio on the Bay.

St. Leonard

8% off
NZ$2,087
for 7 nights, 1 apartment
NZ$298 per night
includes taxes & fees
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
NZ$8,192
for 7 nights, 1 home
NZ$1,170 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.

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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:

  • 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 centre.

Frequently asked questions

What is the best area to stay in Taylors Island when booking a holiday rental?
When considering a holiday rental in Taylors Island, Maryland, the best area to stay is typically around the waterfront locations. This charming area offers a peaceful retreat with stunning views of the Chesapeake Bay. One of the top attractions nearby is the Blackwater National Wildlife Refuge, which is a haven for birdwatchers and nature enthusiasts, providing an opportunity to explore its extensive trails and observe a variety of wildlife.Another point of interest is the local marinas, where you can enjoy activities such as kayaking or fishing, making it an ideal spot for those who appreciate outdoor adventures. The area boasts a limited number of properties, ensuring a more intimate and tranquil experience, allowing visitors to fully immerse themselves in the serene beauty of this picturesque island.
What is the most popular type of holiday rental accomodation in Taylors Island?
In Taylors Island, holiday houses are the predominant type of holiday rental, with around 12 available across the area. These properties typically offer spacious living environments, multiple bedrooms, fully equipped kitchens, and outdoor spaces where guests can relax and enjoy the surrounding natural beauty. Ideal for families or groups, these holiday houses provide a comfortable and homely atmosphere, making them a popular choice for visitors looking to explore the scenic landscapes of Maryland.
Are there any family house rentals in Taylors Island?
In Taylors Island, Maryland, there are several family-friendly house rentals available, making it an excellent choice for those looking to escape for a while. The area is known for its picturesque coastal views and serene atmosphere, superb for families seeking relaxation and outdoor activities. Many of these homes come equipped with spacious living areas, full kitchens, and outdoor decks, where families can enjoy meals together or simply take in the views.Visitors can explore the nearby waterways, which are great for kayaking, fishing, or simply enjoying a day out on the water. The surrounding natural beauty provides ample opportunities for nature walks and birdwatching, making it a fantastic destination for families who appreciate the outdoors.
Are there pet-friendly house rentals in Taylors Island?
In Taylors Island, there are several pet-friendly house rentals available, making it a delightful destination for travellers looking to bring their furry companions along. Many of these holiday homes offer amenities such as spacious yards, outdoor seating areas, and fully equipped kitchens, ensuring a comfortable stay for both humans and pets.The area is known for its peaceful setting and proximity to the Chesapeake Bay, where pets can enjoy walks along the water's edge. Nearby, the Blackwater National Wildlife Refuge offers a range of outdoor activities, including hiking trails that welcome pets on leashes, providing opportunities for memorable adventures.
Are there any remote work holiday rentals in Taylors Island?
In Taylors Island, Maryland, there are several remote work-friendly holiday rentals available, with around 12 options to choose from. This serene island setting offers a peaceful environment for those looking to balance work and leisure. Many of the properties provide essential amenities such as free Wi-Fi, allowing for a seamless remote working experience.The rentals typically feature comfortable workspaces, spacious living areas, and full kitchens, making it easy to prepare meals during your stay. Given the tranquil surroundings, you can also enjoy some downtime by exploring the natural beauty of the island, including local wildlife and picturesque waterfront views. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Taylors Island?
In Taylors Island, popular rental amenities include kitchens, which allow guests to prepare their own meals, and coffee and tea makers for a comforting start to the day. Many properties also feature blenders, superb for whipping up smoothies or other beverages. For those cooler evenings, fireplaces provide a warm and inviting atmosphere. Additionally, the presence of paper towels adds a practical touch, making clean-up easier after meals or activities.
When is the best time to visit Taylors Island for a holiday rental?
The peak season for holiday rentals on Taylors Island is during the summer months, specifically from June to August. This vibrant period attracts families and outdoor enthusiasts eager to enjoy the beautiful Chesapeake Bay, where activities such as kayaking, fishing, and crabbing abound. July stands out as the most popular month, offering warm temperatures and a lively option great for beach outings and water sports.During the summer, visitors can expect comfortable highs averaging around 28 to 32 degrees Celsius, making it ideal for enjoying the island's natural beauty and engaging in outdoor adventures. The pleasant weather also sets the stage for romantic sunset strolls along the shore or picnics in the scenic parks.For those seeking a more budget-friendly experience, consider visiting in November. This month provides a quieter atmosphere, allowing you to explore the island's charm and tranquillity at a more leisurely pace. The cooler temperatures, ranging from 5 to 15 degrees Celsius, make it a wonderful time for peaceful walks and enjoying the local wildlife.Ultimately, the best time to visit Taylors Island depends on whether you prefer the lively summer scene filled with activities or the serene, off-peak experience that November offers.
What are the top attractions in Taylors Island?
In Taylors Island, visitors can enjoy a tranquil escape with natural beauty and unique attractions. The nearby Blackwater National Wildlife Refuge is a significant highlight, offering stunning landscapes, walking trails, and opportunities for birdwatching and wildlife photography. This area is home to a diverse range of species, making it superb for nature enthusiasts.The local community also showcases its maritime heritage, with the Taylors Island Church and the surrounding waterfront areas reflecting the charm of this small fishing village. For those interested in history, the nearby town of Cambridge offers additional attractions, including the Harriet Tubman Museum and Educational Centre, which celebrates the life and legacy of the famous abolitionist.The area's quiet waters are ideal for kayaking and fishing, providing a serene environment for outdoor activities.
Are all fees included in the Taylors Island holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Taylors Island holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Taylors Island holiday homes?
You can find great discounts on holiday homes in Taylors Island on Bookabach, 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.
Can I change or cancel my Taylors Island holiday home booking on Bookabach?
To find Taylors Island holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Taylors Island?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Taylors Island holiday home?
Book your Taylors Island holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Taylors Island?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Taylors Island to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.