Kingston Vacations from $2,024

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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 $2,653, price is now $2,024 per person
$2,024
per person
Jan 3 - Jan 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tortola (EIS)
9.8/10 Exceptional! (152 reviews)
Convenient to beautiful Cane Garden Bay, many eating choices, hotel was fresh and clean and well maintained. Large comfortable rooms and lovely pleasant staff

Reviewed on Oct 10, 2025

Rosewood Little Dix Bay

Rosewood Little Dix Bay

5 out of 5
Save 100% on your flight
Price was $16,265, price is now $9,859 per person
$9,859
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tortola (EIS)
9.2/10 Wonderful! (92 reviews)
Staff was phenomenal

Reviewed on Sep 27, 2025

Scrub Island Resort, Spa & Marina

Scrub Island Resort, Spa & Marina

5 out of 5
Save 100% on your flight
Price was $2,970, price is now $2,039 per person
$2,039
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tortola (EIS)
9/10 Wonderful! (172 reviews)
This was one of the best experiences we've ever had. The hotel is spectacular, as is the shuttle service and the hotel staff. The only thing I didn't like is that when you purchase the stay package, they don't tell you about the room and service fees, and then they charge you at the end of your stay, which are unavoidable. But the stay was truly spectacular!!!

Reviewed on Sep 1, 2025

The Aerial, BVI

The Aerial, BVI

4 out of 5
Save 100% on your flight
Price was $6,906, price is now $4,958 per person
$4,958
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tortola (EIS)
9.6/10 Exceptional! (4 reviews)
Our stay at the Aerial BVI was exceptional. The property is breathtaking, the staff is so kind and cater to your every need. The island has such a special purpose and meaning behind it bad we were so happy to experience it. We took advantage of the horseback riding, spa treatments, night glass bottom kayak ride. The food was all farm to table and healthy and the beach was beautiful. I can’t say enough about the room design and the stunning ocean views. This property is one of a kind and a rare gem. Every detail is so thought out and the focus is on healing and wellness which I love. We will definitely be back and have already told all of our loved ones.

Reviewed on Jul 9, 2024

Oil Nut Bay

Oil Nut Bay

4 out of 5
Save 100% on your flight
Price was $5,689, price is now $4,173 per person
$4,173
per person
Jan 6 - Jan 11
found 6 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tortola (EIS)
10/10 Exceptional! (1 review)
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Discover the most popular places to visit in Kingston

Trunk Bay Beach

Trunk Bay Beach

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

Tortola Cruise Ship Port

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

Anegada Island

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

What to do in Kingston

Lady Lynsey II

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

$149
per adult
86% of travellers recommend
St. Thomas Dinner Sail to St. John with Open Bar & Hors D'oeuvres - Ritz-Carlton
St. John Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin

St. John Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin

$179
per adult
96% of travellers recommend
St. John Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin
Visit the best spots in the US Virgin Islands during this half-day boat charter aboard Bonus Time.

Half or Full-Day Private Boat Charter from St. John or St. Thomas

$795
per traveler
Half or Full-Day Private Boat Charter from St. John or St. Thomas
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
$160 nightly
The price is $175 total per night from Oct 19 to Oct 20
$175 total
Oct 19 - Oct 20
Total with taxes and fees
8/10 Very Good! (781 reviews)
"Comparable to otger more expensive hotels. It only needs better parking area."

Reviewed on Oct 9, 2025

Village Cay Hotel and Marina
Sebastian's on the Beach

Sebastian's on the Beach

3 out of 5
Apple Bay, West End, Tortola
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $91 total per night from Oct 15 to Oct 16
$91 total
Oct 15 - Oct 16
Total with taxes and fees
8.4/10 Very Good! (838 reviews)
"Great stay"

Reviewed on Sep 21, 2025

Sebastian's on the Beach
Nanny Cay Resort and Marina

Nanny Cay Resort and Marina

3 out of 5
Nanny Cay, Road Town, NA
$189 nightly
The price is $206 total per night from Oct 19 to Oct 20
$206 total
Oct 19 - Oct 20
Total with taxes and fees
8.8/10 Excellent! (10 reviews)
"Everything was great. Everything close to the hotel rooms, convenient stores, restaurants."

Reviewed on Oct 11, 2025

Nanny Cay Resort and Marina
See all 442 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.

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 $2,024 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.