Taylors Island Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Black Friday Sale

Save up to 50% on select hotels

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$305 per night from 17 Dec to 18 Dec
S$305
17 Dec - 18 Dec
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
The room was spotless. The staff were courteous and helpful. Fantastic hotel!

Reviewed on 28 Oct, 2025

Hyatt Regency Chesapeake Bay
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
The price is S$153 per night from 25 Nov to 26 Nov
S$153
25 Nov - 26 Nov
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
Love it

Reviewed on 19 Nov, 2025

Rod 'N' Reel Resort
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
The price is S$141 per night from 25 Nov to 26 Nov
S$141
25 Nov - 26 Nov
includes taxes & fees
7.8/10 Good! (967 reviews)
Rooms were clean and the staff were very friendly and helpful.

Reviewed on 20 Nov, 2025

Solomons Inn Resort & Marina
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.

* 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.