Taylors Island Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Taylors Island

Hyatt Regency Chesapeake Bay
Hyatt Regency Chesapeake Bay
4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is S$374 per night from 22 Jul to 23 Jul
S$374
22 Jul - 23 Jul
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"The Hyatt is a great stay. Balconies outside need painting. Staff and amenities otherwise are great."

Reviewed on 22 Jun, 2025

Hyatt Regency Chesapeake Bay
Solomons Inn Resort & Marina
Solomons Inn Resort & Marina
2.5 out of 5
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Fully refundableReserve now, pay when you stay
7.8/10 Good! (803 reviews)
"Staff was excellent. Nice pool & rooms were clean and comfortable."

Reviewed on 21 Jun, 2025

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Solomons Inn Resort & Marina
Rod 'N' Reel Resort
Rod 'N' Reel Resort
4 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (1,001 reviews)
"Huge resort in a small, well kept town! Our room was right on the bay and was clean and nice. The beds and pillows were super comfortable. There is not a place for breakfast but if you go a little further south on the main road, there is a shopping center with a McDonalds (and a CVS and some other ..."

Reviewed on 16 Jun, 2025

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Rod 'N' Reel Resort
See all 495 properties in Taylors Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Taylors Island holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Taylors Island costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Taylors Island?
You can generally find reduced prices and better availability in January, February and November. Take a look at our cheap Taylors Island holiday packages and you could score some great off-season deals.
How many days is enough for Taylors Island?
With a well-organised itinerary, you can easily visit the most popular Taylors Island attractions in a handful of days. But if you prefer to discover hidden gems or go on day tours, consider booking your Taylors Island holiday for longer.
How to find the best Taylors Island package deals?
Use Expedia's filter tool to help you find some unbeatable Taylors Island package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Taylors Island package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book a Taylors Island holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking stays and flights separately. Better still, you can customise your Taylors Island escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Taylors Island?
Enjoy amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Taylors Island holiday.
How to plan a trip to Taylors Island?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Taylors Island.
  2. Plan your budget wisely: On top of the cost of your stay, you'll need to factor in other expenses. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that may crop up during your trip to Taylors Island.
  3. Decide how many days away: Start by listing all the attractions you'd like to get to in Taylors Island. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalised Taylors Island holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.