Cruz Bay Holidays

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Top Cruz Bay Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
Price was £1,362, price is now £929 per person
£929
per person
11 Aug - 18 Aug
found 1 day ago
Return flight included
Chicago (ORD) to St. Thomas (STT)
9/10 Wonderful! (546 reviews)
The room was clean and comfortable, the views were amazing, but the TV didn’t work and it took them a while to “fix it” which they had us move rooms to correct the issue. The

Reviewed on 3 Jul 2026

At Home in the Tropics

At Home in the Tropics

3 out of 5
Price was £1,455, price is now £977 per person
£977
per person
11 Aug - 18 Aug
found 1 day ago
Return flight included
Chicago (ORD) to St. Thomas (STT)
9.8/10 Exceptional! (180 reviews)
Host was amazing, everything was great! Only constructive criticism I’d give is mattress is probably due for an update. Would 1000% stay here again it was excellent!!!

Reviewed on 29 Jun 2026

Hotel 1829

Hotel 1829

4.5 out of 5
Price was £1,737, price is now £1,183 per person
£1,183
per person
11 Aug - 18 Aug
found 1 day ago
Return flight included
Chicago (ORD) to St. Thomas (STT)
9.8/10 Exceptional! (34 reviews)
Ideal location.

Reviewed on 21 Jun 2026

Boundless Bliss Hotel

Boundless Bliss Hotel

2.5 out of 5
Price was £1,410, price is now £1,006 per person
£1,006
per person
11 Aug - 18 Aug
found 1 day ago
Return flight included
Chicago (ORD) to St. Thomas (STT)
6.8/10 (173 reviews)
Ocean view is misleading property is out of the way on top of a hill.Shuttle and taxis do not want the fare.Sole staff member was fantastic.Rooms are outdated 1960’s .

Reviewed on 28 Jun 2026

Windward Passage Hotel

Windward Passage Hotel

3.5 out of 5
Price was £1,413, price is now £1,066 per person
£1,066
per person
11 Aug - 18 Aug
found 1 day ago
Return flight included
Chicago (ORD) to St. Thomas (STT)
7.2/10 Good! (1,481 reviews)
air conditioning was terrible

Reviewed on 2 Jul 2026

Cruz Bay Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Cyril E. King Airport (STT)
Population
2,700

Top hotels in Cruz Bay

The Westin St. John Resort Villas

The Westin St. John Resort Villas

4.5 out of 5
300B Chocolate Hole St. John
The price is £614 per night from 2 Aug to 3 Aug
£614
2 Aug - 3 Aug
includes taxes & fees
8.2/10 Very good! (492 reviews)
"Location to pool was good. Pool wasn’t very clean"

Reviewed on 25 Jun 2026

The Westin St. John Resort Villas
Villa Island Paradise

Villa Island Paradise

4 out of 5
St John St. John St John
The price is £433 per night from 9 Jul to 10 Jul
£433
9 Jul - 10 Jul
includes taxes & fees
9.6/10 Exceptional! (32 reviews)
"Clean, nice area."

Reviewed on 3 Jul 2026

Villa Island Paradise
Cruz Bay Boutique Hotel

Cruz Bay Boutique Hotel

3 out of 5
74-2 Cruz Bay Town St. John
9.6/10 Exceptional! (338 reviews)
"Perfect location, and all you need to have a great trip! Just note there is no parking if you are getting a rental."

Reviewed on 2 Jul 2026

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Cruz Bay Boutique Hotel
See all 1,093 properties in Cruz Bay
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.
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Frequently asked questions

Why should I book my Cruz Bay holiday with Expedia?
Choose Expedia to plan your next break with ease, all in one convenient place. Our top tip for getting a great deal on a Cruz Bay retreat? Bundle your accommodation, flights and/or car hire into a package holiday. Then add a few fun tours and activities. Many bookings also have flexible cancellation policies, so there's no need to panic if you have to change your travel plans. Round-the-clock help with changing and cancelling your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Cruz Bay?
If you enjoy the buzz of peak season, visit Cruz Bay in February, May and July. Travelling during the quieter months of September, October and December will help you avoid the crowds. Plan your getaway to Cruz Bay according to what kind of adventure you want. January is the coolest month, when daytime temperatures average 26ºC. In July, the warmest month, expect averages of 30ºC during the day.
What is the top hotel for my holiday in Cruz Bay?
Offering many of the conveniences and comforts of home, Windward Passage Hotel will make the perfect base for your Cruz Bay holiday.
How do I get a cheap holiday to Cruz Bay?
Creating your own Cruz Bay holiday with Expedia is the easiest way to save. We have over 400 air carriers and 321,000 properties globally. With such a broad range to select from, you'll have no difficulty putting together your dream escape. Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Cruz Bay holiday?
There are plenty of places to visit while on a holiday in Cruz Bay. Magens Bay Beach, Trunk Bay, Coki Point Beach and Blackbeards Castle are among this destination's top attractions.
What is the best area to stay in when on holiday in Cruz Bay?
Cruz Bay has a number of wonderful places to see, including St. John Spice. Book a stay close by and make sightseeing easier.
Do I need a visa for my Cruz Bay holiday?
Look up the most up-to-date information on official government websites. Your nationality and whether you're travelling for work or pleasure will determine if you'll require a visa for Cruz Bay. Get familiar with the application process, including the required documentation, fees and turnaround times. Start your application well in advance to allow sufficient time for processing. Some visas may take weeks or even months to obtain, depending on the country.
What should I wear on my Cruz Bay holiday?
First, consider the sorts of activities you have planned during your Cruz Bay holiday and select versatile pieces that can be mixed and matched. For fashion inspiration or even information on dress codes, look up style blogs or relevant social media accounts. Pack appropriately by monitoring the forecast in Cruz Bay. July brings the warmest temperatures, with daily averages of 30ºC, while January days average 26ºC, making it the coolest month.
What does an Expedia Cruz Bay holiday include?
It's up to you! Simply pick from a variety of Cruz Bay bundles, such as a hire car, hotel and flight. You can also book a flight with a hotel, or a flight and a car hire. Once you've made your booking, add the fun stuff like experiences and tours. Whatever your perfect Cruz Bay holiday looks like, you're sure to save! Villas and condos are a few sought-after property types in Cruz Bay. Whatever your preference or size of your group, you can rely on Expedia for the freedom and flexibility to personalise your next big adventure.
Does Expedia offer Book Now, Pay Later Cruz Bay holidays?
Expedia has teamed up with online lender Klarna to make booking your next getaway easier on the purse strings. Paying in instalments means you can spread the costs of your next big adventure, leaving you with more cash to play with while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that works with your budget. Check out these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds best for you, Klarna offers just that! Paying in multiple instalments will make that dream holiday possible.
  • No-deposit holidays: If not paying upfront for your getaway makes hitting that "book now" button easier, go for a no-deposit holiday plan with Klarna so that you can Book Now, Pay Later!

Can I choose my airline with a Cruz Bay Expedia holiday?
Yes, and with over 400 airlines to select from around the world, you have plenty of choice. Have a look through the available options and find out which airline best fits your budget and needs.

Stay near popular Cruz Bay attractions

Cruz Bay Beach

8.8/10 (51 reviews)
Why not spend a lazy afternoon at Cruz Bay Beach during your trip to St. John? Amble around the area's beautiful beaches or seek out the snorkelling spots.
See properties

What to do in Cruz Bay

Sunset Sail with Cocktails and Appetizers

Sunset Sail with Cocktails and Appetizers

£71
per adult
98% of travellers recommend
Sunset Sail with Cocktails and Appetizers
Night Kayak Tour St. Thomas - Westin Frenchman's Reef

Night Kayak Tour St. Thomas - Westin Frenchman's Reef

£59
per adult
98% of travellers recommend
Night Kayak Tour St. Thomas - Westin Frenchman's Reef
Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove

Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove

£88
per adult
98% of travellers recommend
Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove
See all activities in Cruz Bay

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.