Kingston Vacations from $1,545

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Your Kingston Vacation

Say farewell to planning worries and hello to a Kingston vacation package. With the finer details organized before you go, you can focus on discovering the best of this city, starting with Wickhams Cay 1, which is good for views, dining and shopping. Make your trip to Kingston even more fun and exciting by going sightseeing. Cane Garden Bay Beach, Anegada Island and Nanny Cay are some of the top attractions you'll want to explore. Stop dreaming and start doing. Explore the broad range of options on Expedia today and finally put your Kingston vacation plans in motion!

The Latest Kingston vacation packages

Price found within the past 48 hours. Click for updated prices.
Cane Garden Bay Beach Hotel

Cane Garden Bay Beach Hotel

3.5 out of 5
Price was $1,832, price is now $1,545 per person
$1,545
per person
Aug 15 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Tortola (EIS)
9.8/10 Exceptional! (250 reviews)
Great location, service and amazing views from the balcony

Reviewed on Jun 8, 2026

Scrub Island Resort, Spa & Marina

Scrub Island Resort, Spa & Marina

5 out of 5
Price was $3,715, price is now $2,789 per person
$2,789
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Tortola (EIS)
9/10 Wonderful! (189 reviews)
Everything about the property was wonderful. The private beach was incredible and the staff were so nice and helpful. We will definitely go back

Reviewed on Jun 9, 2026

Coconut Tree Villa

Coconut Tree Villa

3.5 out of 5
Price was $2,152, price is now $1,732 per person
$1,732
per person
Aug 15 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Tortola (EIS)
8.6/10 Excellent! (40 reviews)
Great location near airport !!

Reviewed on Mar 10, 2026

Sugar Mill hotel

Sugar Mill hotel

4 out of 5
Price was $2,950, price is now $2,496 per person
$2,496
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Tortola (EIS)
9.6/10 Exceptional! (72 reviews)
Lovely boutique hotel with the most amazing breakfast you won’t believe. We enjoyed three dinners during our stay and all were sublime. Restaurant view at sunset is unbeatable. We loved our suite 101 with the outdoor shower. Rupert is always at your service with a smile. Book it.

Reviewed on May 23, 2026

Saba Rock Resort

Saba Rock Resort

3.5 out of 5
Price was $2,881, price is now $2,458 per person
$2,458
per person
Jul 28 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Tortola (EIS)
9.8/10 Exceptional! (62 reviews)
The most amazing experience! It's a small island with everything; beach, spa, water sports, boutique, bar with DJ, restaurant, marina, plus a water taxi that takes you to all the other restaurants near by. The staff is friendly and very professional. The rooms are a 5 star level. Highly recommended!

Reviewed on May 13, 2026

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Discover the most popular places to visit in Kingston

Trunk Bay Beach, St John, Virgin Islands National Park, Caribbean

Trunk Bay Beach

4.5/5(215 reviews)

If a restful vacation is part of your travel plans, Trunk Bay Beach might be the perfect place to seek out during your trip to Road Town. Stroll along the seaside or seek out the sailing opportunities.

Trunk Bay Beach
Aerial view of the Caribbean island of Anegada in the British Virgin Islands

Anegada Island

5/5(2 reviews)

Commune with nature and explore the great outdoors at Anegada Island during your travels in Road Town. Wander the beautiful beaches and seaside in this romantic area.

Anegada Island

Tortola Cruise Ship Port

4/5(145 reviews)

Explore the waterfront in Road Town with a trip to Tortola Cruise Ship Port. Wander the beautiful beaches and seaside in this romantic area.

Tortola Cruise Ship Port

What to do in Kingston

St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton

St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton

$319
per adult
St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton
Romantic

St. Thomas Dinner Sail to St. John with Open Bar & Hors D'oeuvres - Ritz-Carlton

$149
per adult
88% of travellers recommend
St. Thomas Dinner Sail to St. John with Open Bar & Hors D'oeuvres - Ritz-Carlton
US Virgin Islands Island Hop & Food Boat Tour

US Virgin Islands Island Hop & Food Boat Tour

$350
per adult
80% of travellers recommend
US Virgin Islands Island Hop & Food Boat Tour
See all activities in Kingston

Kingston Hotel Deals

Village Cay Hotel and Marina

Village Cay Hotel and Marina

3.5 out of 5
Nibbs St Road Town Tortola
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $186 total per night from Jun 23 to Jun 24
$186 total
Jun 23 - Jun 24
Total with taxes and fees
8.2/10 Very Good! (979 reviews)
"Nice place close to marina"

Reviewed on Jun 10, 2026

Village Cay Hotel and Marina
Nanny Cay Resort and Marina

Nanny Cay Resort and Marina

3 out of 5
Nanny Cay Road Town NA
$214 nightly
The price is $235 total per night from Jun 21 to Jun 22
$235 total
Jun 21 - Jun 22
Total with taxes and fees
9.4/10 Exceptional! (214 reviews)
"Arrived after bareboat charter. 3pm check-in was strictly enforced. They stored luggage in the main lobby until check-in."

Reviewed on Jun 11, 2026

Nanny Cay Resort and Marina
Wyndham Tortola BVI Lambert Beach Resort

Wyndham Tortola BVI Lambert Beach Resort

4.5 out of 5
East End East End Tortola
Fully refundableReserve now, pay when you stay
$207 nightly
The price is $228 total per night from Jun 14 to Jun 15
$228 total
Jun 14 - Jun 15
Total with taxes and fees
8.8/10 Excellent! (689 reviews)
"Great place, Beach and service AA++"

Reviewed on Jun 4, 2026

Wyndham Tortola BVI Lambert Beach Resort
See all 659 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.

Find the Best Kingston Vacation Packages

Kingston Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Terrance B. Lettsome Intl. Airport (EIS)
Top Sights
Trunk Bay Beach, St. George’s Anglican Church and Biras Creek Trail

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Frequently asked questions

How much does a Kingston vacation package cost?
You can grab a vacation package to this popular destination from $1,545 on Expedia. However, how much your vacation to Kingston costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Kingston?
May, June and December are great times to look for cheap Kingston vacation packages. Opting to travel in quieter months means you can usually find lower prices on flights and accommodations.
How many days is enough for Kingston?
Typically, a handful of days is enough to check out the top attractions during your Kingston vacation. But if you prefer to have more time to kick back or take day tours, consider extending your trip.
How to find the best Kingston package deals?
Begin your search for a Kingston package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Kingston package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Kingston getaway off to a flying start.
Is it cheaper to book a Kingston vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still have the freedom to create a personalized Kingston vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Kingston?
If you've got your Kingston travel dates locked in, book as soon as you can to score some awesome deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Kingston vacation packages?
Secure your perfect escape to Kingston with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait until your next paycheck — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.