Kingston Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your Kingston Vacation

Our Kingston vacation packages allow you to create your own adventure. Tailor your getaway to your interests and style and make the most of your time in this lively city. During your trip to Kingston, take all the time you need for sightseeing. A fantastic place to begin is Great Hope Golf Course. Whoever you're taking a break with and whatever you want to spend, your dream Kingston vacation is only clicks away with Expedia.

Ready to book your vacation to Kingston?

 

Choose your dates

Kingston Hotel Deals

Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

2.5 out of 5
125 Newtowne Blvd Pocomoke City MD
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Dec 1 to Dec 2
CA $137
CA $153 total
Dec 1 - Dec 2
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Couldn’t take a shower or brush my teeth due to the urine colored water that came out of both the shower & sink…other than that it was amazing. I have video to prove it too."

Reviewed on Nov 13, 2026

Best Western Plus Pocomoke City
Hampton Inn & Suites Salisbury/Fruitland

Hampton Inn & Suites Salisbury/Fruitland

2.5 out of 5
304 Prosperity Lane Fruitland MD
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Nov 22 to Nov 23
CA $156
CA $175 total
Nov 22 - Nov 23
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Great stay"

Reviewed on Nov 13, 2026

Hampton Inn & Suites Salisbury/Fruitland
Home2 Suites By Hilton Salisbury Fruitland

Home2 Suites By Hilton Salisbury Fruitland

3 out of 5
301 Prosperity Lane Fruitland MD
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 24 to Nov 25
CA $162
CA $182 total
Nov 24 - Nov 25
includes taxes & fees
Home2 Suites By Hilton Salisbury Fruitland
See all 162 properties in Kingston
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Kingston vacation package cost?
You can pick up a vacation package to this destination on Expedia. But how much your vacation to Kingston costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Kingston?
If you're looking to snag a cheap Kingston vacation package, consider visiting in January, February and November. You'll typically find lower prices on hotels and flights during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Kingston?
Typically, a handful of days is enough to see the major sights during your Kingston vacation. However, if you want to have some time to rest or go on day trips, think about extending your trip.
How to find the best Kingston package deals?
Use Expedia's handy filters to find some unbeatable Kingston package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Kingston package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Kingston vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component separately. And you'll still get the freedom to create a customized Kingston vacation by choosing your preferred airline, accommodation type and car class.
How to plan a trip to Kingston?

  1. Choose when to travel: Check your schedule and get packing. Your favourite time of year and the activities on offer will also help you decide when to vacation in Kingston.
  2. Set your budget: Factor in expenses like transportation, flights and meals when calculating how much to put aside for your trip to Kingston. Then, select a property that works with your budget, whether that's an affordable stay or a more luxurious getaway.
  3. Determine how many days away: Start by listing all the activities and sights you want to experience in Kingston. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Kingston vacation package that brings all your bookings together.

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