Taylors Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Taylors Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Motel 6 Pocomoke City, MD
CA $932
per person
Oct 14 - Oct 17
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
5.2/10 (506 reviews)
Highly recommend you find a different property and avoid this one at all costs. Will not be staying here or anywhere near here again. We only stayed one night and were there for less than 12 hours. In that time frame. Our jeep was vandalized. The radio antenna of all things… the property is super sketchy. AVOID AVOID AVOID. You’ve been warned…
Reviewed on Aug 3, 2026
Princess Royale Oceanfront Resort
North Ocean City
CA $1,133
per person
Oct 14 - Oct 17
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.8/10 Excellent! (2,606 reviews)
Princess Royal is like a resort property rather than a standard hotel. The rooms are like a condominium equiped with a refridgerator, a range and standard kitchen appliances. Princess Royal is great for family vacation. Whenever we decide to visit Ocean City, MD, we will definitely seek Princess Royal as our vacation stay.
Reviewed on Aug 21, 2026
Fenwick Shores, Tapestry Collection by Hilton
CA $1,094
per person
Oct 14 - Oct 17
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
9.4/10 Exceptional! (809 reviews)
Rooms were clean, staff was excellent and friendly. You could order breakfast but there were plenty of places nearby that you could also try. We went ti Jimmy's which was a good breakfast option.
Great to be able to walk right down to the beach. They need to put in a steamer or iron for use.
Reviewed on Aug 21, 2026
Studio 6 Suites Pocomoke City, MD
CA $946
per person
Oct 14 - Oct 17
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
7.4/10 Good! (77 reviews)
Roof repair was ongoing during our stay.
Daily room service was nice.
First room had problems and we were switched to a much better room.
Internet WIFI was sketchy most of our stay.
Reviewed on Aug 14, 2026
Ready to book your vacation to Taylors Island?
Taylors Island Hotel Deals
About Time! - Remote Waterfront Home with Dock - Sleeps 15-New EV Charger!
Taylors Island MD
10/10 Exceptional! (6 reviews)
"Great place for a large family gathering. Kitchen is well stocked, kayaks and crab traps were fun for the kids. Had a wonderful time around the fire pit at night making s’mores, kept the bugs away too! Not a whole lot to do in the nearby area, so need to bring your own fun. Place was well stocked ..."
Reviewed on Aug 8, 2026
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
CA $242
CA $314 total
Sep 1 - Sep 2
includes taxes & fees
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
CA $291
CA $396 total
Sep 3 - Sep 4
includes taxes & fees
8.8/10 Excellent! (1,022 reviews)
"Excellent well-maintained rooms with new ceiling fan. Summer amenities are geared to families and include mini golf, multiple pools indoors & outdoors, day spa, convenience shop with coffee , pool tables (although not as well maintained as other areas of the property), walking paths, and a regulationgolf ..."
Reviewed on Aug 20, 2026
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 vacation package cost?
You can pick up a vacation package to this top destination from CA $932 on Expedia. But how much your vacation to Taylors Island costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Taylors Island?
January, February and November are the best times to look for cheap Taylors Island vacation packages. Opting to travel in less busy periods means you can typically find reduced prices on flights and accommodations.
How many days is enough for Taylors Island?
Typically, a handful of days is enough to go to the major attractions during your Taylors Island vacation. But if you'd like to have some time to unwind or take day tours, think about extending your itinerary.
How to find the best Taylors Island package deals?
Begin your search for a Taylors Island package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Taylors Island package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Taylors Island escape underway.
Is it cheaper to book a Taylors Island vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations individually. Better still, you can customize your Taylors Island escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Taylors Island?
Secure amazing discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Taylors Island break.
How to plan a trip to Taylors Island?
- Choose when to get away: Check your diary and get your bags packed. Your favourite season and the activities on offer will also help you decide when to escape to Taylors Island.
- Plan your budget wisely: As well as the price of your accommodations, you'll need to consider other expenses. These include flights, transportation and food. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Taylors Island.
- Decide your trip length: Think about how long you'd like to spend discovering Taylors Island. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Taylors Island vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
