Taylors Island Vacation Packages

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Top Taylors Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Motel 6 Pocomoke City, MD

Motel 6 Pocomoke City, MD

2 out of 5
Price was CA $1,194, price is now CA $1,029 per person
CA $1,029
per person
Aug 15 - Aug 21
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
5.2/10 (500 reviews)
Too many flys in room

Reviewed on Jun 17, 2026

Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was CA $1,218, price is now CA $1,047 per person
CA $1,047
per person
Aug 15 - Aug 21
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
7.6/10 Good! (70 reviews)
We stayed for one night and it was definitely a great place for it plus we got lost on where our room is and even though it was late the guy was very nice to still be nice and help us out(:

Reviewed on Jul 1, 2026

Home2 Suites by Hilton Lewes Rehoboth Beach

Home2 Suites by Hilton Lewes Rehoboth Beach

3 out of 5
Price was CA $1,379, price is now CA $1,263 per person
CA $1,263
per person
Sep 17 - Sep 20
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Salisbury (SBY)
9.4/10 Exceptional! (1,004 reviews)
We had a great stay. The location was convenient. I would definitely recommend. When I return, I will rebook.

Reviewed on Jul 3, 2026

Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was CA $1,198, price is now CA $1,106 per person
CA $1,106
per person
Sep 17 - Sep 20
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Salisbury (SBY)
8.8/10 Excellent! (1,018 reviews)

Kingsbay Mansion & Vacation Houses

Kingsbay Mansion & Vacation Houses

3.5 out of 5
Price was CA $2,454, price is now CA $2,288 per person
CA $2,288
per person
Aug 15 - Aug 21
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
9.8/10 Exceptional! (28 reviews)
Jerry & David were wonderful hosts and made us feel welcome and comfortable. They surprised us with an incredible breakfast. We’ll be back, for sure.

Reviewed on Jun 16, 2024

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Taylors Island Hotel Deals

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 CA $425 per night from Jul 7 to Jul 8
CA $425
CA $550 total
Jul 7 - Jul 8
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Only thing was for older and senior people the toilet was to low the the floor, they need to be higher."

Reviewed on Jul 4, 2026

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 CA $225 per night from Jul 8 to Jul 9
CA $225
CA $297 total
Jul 8 - Jul 9
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Excelleny"

Reviewed on Jul 2, 2026

Rod 'N' Reel Resort
avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

3 out of 5
23274 Three Notch Road California MD
Fully refundable
The price is CA $133 per night from Jul 23 to Jul 24
CA $133
CA $148 total
Jul 23 - Jul 24
includes taxes & fees
9.4/10 Exceptional! (141 reviews)
"A good over night accommodation. Staff was very helpful and friendly. Plenty of eating places near by. A good place to stay if your touring Southern Maryland."

Reviewed on Jul 1, 2026

avid hotel California - Lexington Park by IHG
See all 536 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.
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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 $1,029 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.