Taylors Island Vacations from $1,244

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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

The Latest Taylors Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Cambridge Inn
Marvel's on the Creek
St Michaels Inn
Holiday Inn Express Annapolis East-Kent Island by IHG
Hyatt Place Kent Narrows & Marina
Don't see what you're looking for?
See all available trips from Boydton to Taylors Island
View all trips

Taylors Island Hotel Deals

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
$184 nightly
The price is $209 total per night from Nov 23 to Nov 24
$209 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,012 reviews)
Pleasant staff, clean accommodations although could benefit from a modern upgrade. Restaurant was knowledgeable and helpful in assisting my wife with accommodating celiac options.

Reviewed on Oct 26, 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
$115 nightly
The price is $128 total per night from Nov 30 to Dec 1
$128 total
Nov 30 - Dec 1
Total with taxes and fees
7.8/10 Good! (950 reviews)
Great place, I would stay again.

Reviewed on Oct 26, 2025

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
$116 nightly
The price is $127 total per night from Nov 16 to Nov 17
$127 total
Nov 16 - Nov 17
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
we did not have the breakfast, the beds are amazingly comfortable rooms spotless. The water pressure was poor. The staff was over the top helpful and friendly. We would definitely stay again.

Reviewed on Oct 25, 2025

Rod 'N' Reel Resort
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

More vacations you might like

Frequently asked questions

How much does a Taylors Island vacation package cost?
Offering great value package deals from $1,244 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.

Explore a world of travel with Expedia

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