Charlestown Vacations from $1,000

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Your Charlestown Vacation

There's no better way to escape than with one of our vacation packages to Charlestown. The rich history and coastal scenery are just a couple of the countless reasons you'll want to stay in this fascinating city. A trip to Charlestown is a great opportunity to go sightseeing. Make sure you visit well-known attractions like Tobago Cays, Mount Royal and Canouan Golf Club. Stop daydreaming and start adventuring. Explore the wide range of options on Expedia today and put your Charlestown vacation plans in motion!

The Latest Charlestown vacation packages

Price found within the past 48 hours. Click for updated prices.
Bequia Plantation Hotel

Bequia Plantation Hotel

3.5 out of 5
Price was $1,182, price is now $1,000 per person
$1,000
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Argyle (SVD)
9.2/10 Wonderful! (396 reviews)
The rooms where lovely,and the Birthday surprise of the beds for my kids were beautiful.Thank you for a memorable stay.

Reviewed on Jun 1, 2026

Mandarin Oriental, Canouan

Mandarin Oriental, Canouan

5 out of 5
Save 100% on your flight
Price was $6,782, price is now $4,598 per person
$4,598
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Canouan Island (CIW)
9.8/10 Exceptional! (6 reviews)
LA Vue Boutique Hotel & Beach Club

LA Vue Boutique Hotel & Beach Club

3.5 out of 5
Price was $1,453, price is now $1,093 per person
$1,093
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Argyle (SVD)
8.2/10 Very Good! (100 reviews)
Beach access, nice clean hotel, food good, friendly staff

Reviewed on Jun 20, 2026

Soho Beach House Canouan

Soho Beach House Canouan

2.5 out of 5
Price was $2,809, price is now $2,306 per person
$2,306
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Canouan Island (CIW)
10/10 Exceptional! (4 reviews)
The Liming Bequia

The Liming Bequia

4.5 out of 5
Price was $1,771, price is now $1,495 per person
$1,495
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Argyle (SVD)
9.6/10 Exceptional! (115 reviews)
Very relaxing and quite resort. I solo traveled and enjoyed every moment of it! Beautiful room with a private pool and right by the beach. The staff was very friendly and helpful. I recommend going to Princess Margaret beach.

Reviewed on May 16, 2026

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Charlestown Hotel Deals

Mandarin Oriental, Canouan

Mandarin Oriental, Canouan

5 out of 5
Carenage Bay Canouan Island
$1,352 nightly
The price is $1,514 total per night from Jun 22 to Jun 23
$1,514 total
Jun 22 - Jun 23
Total with taxes and fees
9.8/10 Exceptional! (6 reviews)
"An absolutely incredible experience; start to finish! Pre-departure, the hotel staff ensure smooth airport transfers as well as a full menu of daily activities to consider. Upon arrival and throughout our stay, Mandarin's hotel staff exceeded our expectations. There is plenty to do on the premises ..."

Reviewed on May 2, 2022

Mandarin Oriental, Canouan
Soho Beach House Canouan

Soho Beach House Canouan

2.5 out of 5
Grand Bay Canouan Island Saint Vincent and the Grenadines
$806 nightly
The price is $889 total per night from Jun 23 to Jun 24
$889 total
Jun 23 - Jun 24
Total with taxes and fees
Soho Beach House Canouan
Canouan Estate Resort & Villas

Canouan Estate Resort & Villas

4 out of 5
Carenage Bay Canouan Island Grenadines
10/10 Exceptional! (1 review)
Exceptional
"It’s hard to overstate the elegance of the Resort villas. Complete with maid and butler. Very expensive weekend though."

Reviewed on Mar 4, 2024

Get rates
Canouan Estate Resort & Villas
See all 52 properties in Charlestown
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 Charlestown Vacation Packages

Charlestown Essential Information

Language
English
Currency
East Caribbean dollars
Max Temp Winter
80ºF
Max Temp Summer
80ºF
Top Sights
Chatham Bay Beach, Belmont Bay and Captain Hugh Mulzac Square

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Frequently asked questions

How much does a Charlestown vacation package cost?
Offering great value package deals from $1,000 on Expedia, you'll be surprised at how little a vacation to Charlestown costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Charlestown?
You can usually find reduced prices and better availability in January, July and October. Check out our cheap Charlestown vacation packages and you could score some great off-season discounts.
How many days is enough for Charlestown?
Generally, a handful of days is enough to check out the major attractions during your Charlestown vacation. But if you want to have time to relax or go on day tours, think about extending your itinerary.
How to find the best Charlestown package deals?
Start your search for a Charlestown package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Charlestown package deal straight away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Charlestown getaway off to a flying start.
Is it cheaper to book a Charlestown vacation as a package?
You can enjoy significant savings on your next Charlestown retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Charlestown?
Land amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Charlestown escape.
How to plan a trip to Charlestown?

  1. Choose your travel dates: What you'd like to do in Charlestown and your preferred season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and airfares. Your accommodations will probably be the largest expense during your trip to Charlestown.
  3. Organize your Charlestown getaway with our trip planning tool: Look for and book hotels and experiences all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Charlestown together.
  4. Decide how long to go away for: Now that you're up to speed on Charlestown, you can work out the right length of your break. Create a rough itinerary and give yourself enough time to cover everything you want to see.
  5. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Charlestown vacation package that brings all your bookings together.
  6. Add on excursions and experiences: Read our dedicated travel guide to find some exciting things to do in Charlestown. Book tickets or make reservations in advance to save time and skip the hassle of trying to find activities when you arrive.

Does Expedia offer Book Now, Pay Later Charlestown vacation packages?
Secure your dream getaway to Charlestown with our Book Now, Pay Later vacations. There's no need to save like crazy or wait until your next paycheck — we've teamed up with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to budget for your trip and snap up cheap deals before they sell out.

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.