Taylors Island holiday rentals

We found 124 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:20 Nov - 27 Nov

Outdoor banquet area
Exterior
two twin beds and play area in loft
view from balcony overlooking playhouse, pergola and Brooks Creek
Exceptional
(274 reviews)

Family and Pet-Friendly, Waterfront with Pier

Cambridge

8% off
S$2,986
for 7 nights, 1 cottage
S$427 per night
includes taxes & fees
Family and Pet-Friendly, Waterfront with Pier
Living Room into Kitchen/Dining
Foyer into Living Room
Kitchen with peak into living room
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
S$5,673
for 7 nights, 1 home
S$810 per night
includes taxes & fees
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Terrace/patio
Dining
Exterior
Living area
Exceptional
(5 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
S$5,565
for 7 nights, 1 home
S$795 per night
includes taxes & fees
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Living area
Outdoor dining
Interior
Interior
Exceptional
(5 reviews)

Driftwood Haven, Chesapeake Bay views throughout

Lusby

12% off
S$4,404
for 7 nights, 1 home
S$629 per night
includes taxes & fees
Driftwood Haven, Chesapeake Bay views throughout
Exterior
Outdoor dining
Exterior detail
Outdoor dining
Exceptional
(172 reviews)

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

St. Leonard

6% off
S$1,912
for 7 nights, 1 cottage
S$273 per night
includes taxes & fees
Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
Exterior
entryway
steps to the loft
dining area
Exceptional
(56 reviews)

Soul Oasis - home on the Chesapeake Bay

Lusby

8% off
S$1,693
for 7 nights, 1 cottage
S$242 per night
includes taxes & fees
Soul Oasis - home on the Chesapeake Bay
Exterior detail
Living area
Private kitchen
View of parking pad 1 car is  backed in and 1 for studio on the bay pulled in.
Exceptional
(31 reviews)

Studio on the Bay.

St. Leonard

8% off
S$1,717
for 7 nights, 1 apartment
S$245 per night
includes taxes & fees
Studio on the Bay.
Living area
Exterior
Private kitchen
Dining
Exceptional
(27 reviews)

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

Cambridge

8% off
S$6,242
for 7 nights, 1 home
S$892 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

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

How much does it cost to rent a holiday rental in Taylors Island?
Different things influence what you'll pay for a holiday rental in Taylors Island, including the length of stay, season and type of property. But, all Vrbo homes have something in common — excellent value. Simply add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Taylors Island?
Prices for beach houses in Taylors Island may vary depending on the size and style of the property and when you're travelling. Just enter your travel dates into Vrbo and how many guests to view holiday rental options and prices. From there you can use our filters to refine your search by nearby activities, amenities, ratings and more.
How old do you have to be to rent a holiday rental in Taylors Island?
The minimum age can differ between properties on Vrbo, so look at the rules of the holiday rental in Taylors Island you want to book. But usually, it's 16, 18 or 21.
How long can I rent a holiday rental in Taylors Island for?
The amount of time you can rent a Taylors Island holiday rental for varies depending on the property. Just put in your travel dates to see available options that offer long-term stays. They include all the things you need to make your extended break more enjoyable and comfortable, like kitchens and air conditioning. Some properties may also offer weekly or monthly discounted prices, so you can stay even longer for less.