Anna's Retreat Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Anna's Retreat
The Westin St. Thomas Beach Resort & Spa
5 Estate Bakkeroe St. Thomas St. Thomas
S$480
1 Oct - 2 Oct
includes taxes & fees
8.4/10 Very good! (1,447 reviews)
"The views are amazing . The rooms and pools were clean. Enjoyed the staff , very accommodating."
Reviewed on 1 Sept, 2026
Bluebeard's Castle Resort
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
S$290
30 Sept - 1 Oct
includes taxes & fees
Margaritaville Vacation Club - St. Thomas
6080 Estate Smith Bay St. Thomas
8/10 Very good! (2,522 reviews)
"Loved this stay! I went in may. Super fun and friendly staff. Can’t wait to go back"
Reviewed on 1 Sept, 2026
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.
Stay near popular Anna's Retreat attractions
Pistarckle Theater
10.0/10 (1 review)
You can enjoy a show at Pistarckle Theater during your stay in Estate Charlotte Amalie. Stroll along the beautiful beaches in this romantic area or seek out the snorkelling spots.
What to do in Anna's Retreat
Night Kayak Tour St. Thomas - Westin Frenchman's Reef
S$100
per adult
96% of travellers recommend
Key N Go: Guided UTV/ATV Adventure in St. Thomas, USVI (1.5-2 HR)
S$203
per adult
86% of travellers recommend
Frequently asked questions
How much does an Anna's Retreat holiday package cost?
You'll find cheap prices on Expedia for your Anna's Retreat escape. However, a range of factors like the length of stay, hotel choice and season will determine how much your holiday to Anna's Retreat costs.
What are the cheapest months to go to Anna's Retreat?
September, October and November are the best times to look for cheap Anna's Retreat holiday packages. Travelling in less busy periods means you can usually find reduced prices on flights and hotels.
How many days is enough for Anna's Retreat?
Generally, a handful of days is enough to explore the major attractions during your Anna's Retreat holiday. But if you'd like to have some time to chill out or go on day trips, consider extending your trip.
How to find the best Anna's Retreat package deals?
Landing a cheap Anna's Retreat package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can customise your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Anna's Retreat package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book an Anna's Retreat holiday as a package?
You can enjoy significant savings on your Anna's Retreat break by booking a tailored holiday package. Click on the "Package" heading, then enter your destination and travel dates to see some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Anna's Retreat?
If you've got your Anna's Retreat travel dates locked in, book as soon as you can to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Anna's Retreat?
- Choose when to travel: Check your calendar and get packing. Your favourite time of year and the type of activities available will also help you decide when to escape to Anna's Retreat.
- Set a budget: Consider expenses like flights, food and transportation when working out how much to save for your trip to Anna's Retreat. Then, select a property that suits your budget, whether that's a wallet-friendly option or a deluxe retreat.
- Decide how many days away: Start by making a list of all the sights and activities you'd like to get to in Anna's Retreat. Then, estimate how long you'll need at each, as well as any travel time.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalised Anna's Retreat holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
