Taylors Island Vacations from $334

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The Latest Taylors Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was $432, price is now $334 per person
$334
per person
Feb 28 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8.8/10 Excellent! (1,002 reviews)
Clean room, good staff

Reviewed on Dec 18, 2025

Hampton Inn Milford

Hampton Inn Milford

2.5 out of 5
Price was $590, price is now $460 per person
$460
per person
Feb 28 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8.6/10 Excellent! (980 reviews)
I left another hotel because of the horrible condition Best Western Galaxy. Hampton Inn was an excellent experience I would recommend this hotel and give it 5 Stars : very clean hallways/carpet. clean dining area /common area and great customer service very friendly yet professional. Great rooms comfortable beds super sound proof. Finally I just give it 5 Stars and a thumbs UP!

Reviewed on Dec 8, 2025

Beach House Dewey

Beach House Dewey

2.5 out of 5
Price was $461, price is now $373 per person
$373
per person
Feb 28 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8.4/10 Very Good! (788 reviews)
Room was clean, employees very friendly and location w as great.

Reviewed on Nov 4, 2025

Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG

Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG

2.5 out of 5
Price was $569, price is now $475 per person
$475
per person
Feb 28 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (1,001 reviews)
I stayed with this hotel chain because it is one of my favorite chains. This is the first time in 10 years that I was disappointed. The staff wasn't as friendly as I am normally use to. The shower wasn't cleaned properly. When the water began to run old soap scum ran into the shower and on my feet. This isn't the normal standards that I am use to experiencing with this chain and won't utilize this property again.

Reviewed on Oct 16, 2025

avid hotel Millsboro Georgetown South by IHG

avid hotel Millsboro Georgetown South by IHG

2.5 out of 5
Price was $535, price is now $449 per person
$449
per person
Feb 28 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
9.2/10 Wonderful! (471 reviews)
Everything here was excellent. The hotel front desk clerk was helpful and nice. Our room was very clean and quite comfortable. It is very convenient to restaurants and stores. We would definitely stay here again when visiting family.

Reviewed on Nov 17, 2025

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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
$176 nightly
The price is $200 total per night from Jan 1 to Jan 2
$200 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Enjoyed everything about my one night stay. The staff was very hospitable and accommodating. The room was awesome with a very nice view of the surrounding water. Overall, a very positive experience.

Reviewed on Dec 5, 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
$121 nightly
The price is $132 total per night from Dec 27 to Dec 28
$132 total
Dec 27 - Dec 28
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
Room was nice, except for the heating system, which was noisy and seemed to blow cool air

Reviewed on Dec 13, 2025

Rod 'N' Reel Resort
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

3 out of 5
22769 Three Notch Rd California MD
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $98 total per night from Jan 2 to Jan 3
$98 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
7.6/10 Good! (1,002 reviews)
Staff very friendly,, room was very nice and clean, good location for business I was in town for

Reviewed on Dec 17, 2025

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
See all 506 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.

Find the Best Taylors Island Vacation Packages

Taylors Island Essential Information

Language
English
Currency
U.S dollars
Population
170
Top Sights
Jefferson Patterson Park and Museum, Perigeaux Vineyards and Winery and Cove Point Lighthouse

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Frequently asked questions

How much does a Taylors Island vacation package cost?
Offering great value package deals from $334 on Expedia, you'll be surprised at how little a vacation 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're likely to find lower prices and greater availability in November, December and January. Explore our cheap Taylors Island vacation packages and you could score some great off-season discounts.
How many days is enough for Taylors Island?
The ideal duration for your Taylors Island vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you enough time to go to all the major attractions and discover some hidden spots along the way.
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 vacation package well in advance.
Is it cheaper to book a Taylors Island vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking stays and flights separately. Better still, you can customize 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 vacation 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 vacation.
Does Expedia offer Book Now, Pay Later Taylors Island vacation packages?
Secure your dream getaway to Taylors Island with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for payday — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stick to your budget and snap up travel deals before they disappear.

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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.