Anna's Retreat Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Alex's Outdoor Escapes

Top hotels in Anna's Retreat

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay, St. Thomas
The price is 6.855.716 ₫ per night from 27 Aug to 28 Aug
6.855.716 ₫
7.712.681 ₫ total
27 Aug - 28 Aug
includes taxes & fees
8/10 Very Good! (2,204 reviews)
"Loved everything about it , especially the breakfast in the store"

Reviewed on 23 Aug 2025

Margaritaville Vacation Club - St. Thomas
The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

4.5 out of 5
5 Estate Bakkeroe, Po Box 7100, St. Thomas, St. Thomas
Fully refundableReserve now, pay when you stay
The price is 7.479.585 ₫ per night from 24 Sept to 25 Sept
7.479.585 ₫
10.574.473 ₫ total
24 Sept - 25 Sept
includes taxes & fees
8.2/10 Very Good! (1,018 reviews)
"The property was beautiful and clean. Comfortable room with a beautiful view"

Reviewed on 25 Aug 2025

The Westin St. Thomas Beach Resort & Spa
Windward Passage Hotel

Windward Passage Hotel

3.5 out of 5
Veterans Drive Charlotte Amali, Po Box 640, St. Thomas, St. Thomas
Fully refundableReserve now, pay when you stay
7/10 Good! (1,377 reviews)
"Area"

Reviewed on 23 Aug 2025

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Windward Passage Hotel
See all 3,709 properties in Anna's Retreat
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.

Popular places to visit

Pistarckle Theater

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.

Pistarckle Theater

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.