Head of The Bay Vacations from $1,402

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Your Head of The Bay Vacation

Book a tailored Head of The Bay vacation package that includes everything you need and nothing you don't. Great for views, dining and shopping, think about basing yourself in the neighborhood of Wickhams Cay 1. If taking in sights is on the cards during your trip to Head of The Bay, swing by leading attractions like The Baths, Little Dix Bay Beach and Leverick Bay Marina. Browse Expedia's extensive range of travel options and start planning your perfect vacation to Head of The Bay now.

The Latest Head of The Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
Leverick Bay Resort and Marina

Leverick Bay Resort and Marina

3 out of 5
Price was $1,718, price is now $1,402 per person
$1,402
per person
Jan 18 - Jan 22
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Spanish Town (VIJ)
8.8/10 Excellent! (38 reviews)
-

Reviewed on Sep 11, 2026

Bitter End Yacht Club

Bitter End Yacht Club

3.5 out of 5
Price was $13,268, price is now $9,883 per person
$9,883
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Spanish Town (VIJ)
9.2/10 Wonderful! (49 reviews)
Excellent experience and the staff was wonderful. Definitely will return.

Reviewed on Jul 28, 2026

Rosewood Little Dix Bay

Rosewood Little Dix Bay

5 out of 5
Price was $5,088, price is now $4,125 per person
$4,125
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Spanish Town (VIJ)
9.4/10 Exceptional! (118 reviews)
Great place, will be back!

Reviewed on Aug 5, 2026

Bayview Vacation Apartments

Bayview Vacation Apartments

3.5 out of 5
Price was $1,878, price is now $1,592 per person
$1,592
per person
Jan 18 - Jan 22
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Spanish Town (VIJ)
9.6/10 Exceptional! (26 reviews)
Fabulous location, spacious condo, very clean.

Reviewed on Jun 24, 2026

Oil Nut Bay

Oil Nut Bay

4 out of 5
Price was $5,150, price is now $4,380 per person
$4,380
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Spanish Town (VIJ)
10/10 Exceptional! (5 reviews)
Beautiful resort

Reviewed on May 27, 2026

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What to do in Head of The Bay

Private Hiking Tour in British Virgin Island with the Best 360 View

Private Hiking Tour in British Virgin Island with the Best 360 View

$100
per adult
Private Hiking Tour in British Virgin Island with the Best 360 View
BVI Private Day Charters

BVI Private Day Charters

$1,236
per traveler
BVI Private Day Charters
Baths of Virgin Gorda

Discover The Baths of Virgin Gorda Full Day Adventure - Westin St. John

$339
per adult
100% of travellers recommend
Discover The Baths of Virgin Gorda Full Day Adventure - Westin St. John
See all activities in Head of The Bay

Head of The Bay 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
$190 nightly
The price is $207 total per night from Nov 7 to Nov 8
$207 total
Nov 7 - Nov 8
Total with taxes and fees
Village Cay Hotel and Marina
Cane Garden Bay Beach Hotel

Cane Garden Bay Beach Hotel

3.5 out of 5
Rte 1 Cane Garden Bay Tortola
$450 nightly
The price is $489 total per night from Nov 7 to Nov 8
$489 total
Nov 7 - Nov 8
Total with taxes and fees
9.8/10 Exceptional! (308 reviews)
"Staff was always attentive and friendly. Property was always clean and beautiful."

Reviewed on Nov 2, 2026

Cane Garden Bay Beach Hotel
Wyndham Tortola BVI Lambert Beach Resort

Wyndham Tortola BVI Lambert Beach Resort

4.5 out of 5
East End East End Tortola
Fully refundableReserve now, pay when you stay
$226 nightly
The price is $246 total per night from Nov 8 to Nov 9
$246 total
Nov 8 - Nov 9
Total with taxes and fees
8.8/10 Excellent! (747 reviews)
"Staff was very helpful"

Reviewed on Nov 4, 2026

Wyndham Tortola BVI Lambert Beach Resort
See all 698 properties in Head of The 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.

Find the Best Head of The Bay Vacation Packages

Head of The Bay Beach Vacation

Get prepared to live out your beach fantasies on your upcoming Head of The Bay vacation. Set off on a lovely walk, take in the gorgeous coastal views and collect pretty seashells on your trip to Head of The Bay. Situated just 0.4 miles (0.6 km) from the city center, Little Dix Bay Beach is the place to be for many visitors. Have a look through our Head of The Bay vacation deals and watch your travel budget go further!

Head of The Bay Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Terrance B. Lettsome Intl. Airport (EIS)
Top Sights
The Baths, The Baths National Park and Gorda Peak National Park

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Frequently asked questions

How much does a Head of The Bay vacation package cost?
You can snap up a vacation package to this destination from $1,402 on Expedia. However, how much your vacation to Head of The Bay costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Head of The Bay?
If you're looking to score a cheap Head of The Bay vacation package, consider visiting in June, August and December. You'll typically find better rates on airfares and hotels during these months — ideal for a budget-friendly break.
How many days is enough for Head of The Bay?
The ideal length for your Head of The Bay vacation depends on what you'd like to do and see. Generally, a few days to a week will give you time to check out all the top attractions and discover some hidden spots along the way.
How to find the best Head of The Bay package deals?
Begin your search for a Head of The Bay package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Head of The Bay package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Head of The Bay adventure underway.
Is it cheaper to book a Head of The Bay vacation as a package?
You can enjoy significant savings on your next Head of The Bay escape by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to see the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Head of The Bay?
If you have your Head of The Bay travel dates finalized, book early to score some terrific deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Head of The Bay vacation packages?
If you're anything like us, you love exploring new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Head of The Bay break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.