Head of The Bay Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

Top Head of The Bay Vacation Deals

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 CA $2,076, price is now CA $1,890 per person
CA $1,890
per person
Sep 1 - Sep 6
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Spanish Town (VIJ)
8.8/10 Excellent! (34 reviews)
This was a beautiful resort to stay at. I was there to visit my family after my precious Uncle passed away. The resort was within walking distance of my family’s home. The staff was so welcoming and helpful. Highly recommended.

Reviewed on May 14, 2026

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 0.64 kilometres 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!

Ready to book your vacation to Head of The Bay?

 

Choose your dates

Head of The Bay Hotel Deals

Nanny Cay Resort and Marina

Nanny Cay Resort and Marina

3 out of 5
Nanny Cay Road Town NA
The price is CA $287 per night from Jul 20 to Jul 21
CA $287
CA $345 total
Jul 20 - Jul 21
includes taxes & fees
9.4/10 Exceptional! (234 reviews)
"You can’t beat the location of Nanny Caye if you are using the marina. Keep in mind that boaters start their mornings very early and the staff starts using the leaf blower at 7 am!!! Other than that, the room and property are fabulous! Avoid Peg Leg bar/resteraunt! The staff is rude and you’ll wait ..."

Reviewed on Jul 4, 2026

Nanny Cay Resort and Marina
Wyndham Tortola BVI Lambert Beach Resort

Wyndham Tortola BVI Lambert Beach Resort

4.5 out of 5
East End East End Tortola
The price is CA $262 per night from Jul 9 to Jul 10
CA $262
CA $315 total
Jul 9 - Jul 10
includes taxes & fees
8.8/10 Excellent! (702 reviews)
"Clean Stocked"

Reviewed on Jul 2, 2026

Wyndham Tortola BVI Lambert Beach Resort
Village Cay Hotel and Marina

Village Cay Hotel and Marina

3.5 out of 5
Nibbs St Road Town Tortola
The price is CA $230 per night from Jul 19 to Jul 20
CA $230
CA $272 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very good! (1,003 reviews)
"The staff stayed late (after 10pm) to welcome me when I arrived."

Reviewed on Jul 6, 2026

Village Cay Hotel and Marina
See all 700 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Head of The Bay

Full-Day Charter To The Baths Virgin Gorda British Virgin islands

Full-Day Charter To The Baths Virgin Gorda British Virgin islands

CA $6,746
per traveller
Full-Day Charter To The Baths Virgin Gorda British Virgin islands
"Seas the Day!" Hop to iconic BVI islands and amazing snorkeling.

"Seas the Day!" Hop to iconic BVI islands and amazing snorkeling.

CA $2,400
per traveller
"Seas the Day!" Hop to iconic BVI islands and amazing snorkeling.
See all activities in Head of The Bay

Frequently asked questions

How much does a Head of The Bay vacation package cost?
Offering excellent value package deals from CA $1,890 on Expedia, you'll be pleasantly surprised at how much a vacation to Head of The Bay costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Head of The Bay?
The off-season is the best time to head to Head of The Bay if you're trying to save. Another tip for getting cheap Head of The Bay vacation packages? Try to avoid public holidays and any major festivals.
How many days is enough for Head of The Bay?
When planning your Head of The Bay vacation, a few days will be enough to tour the top spots. Make sure to visit Gorda Peak National Park — it's one of the top sights in this destination. If you're looking for more adventure, consider basing yourself here and venturing off on some tours from Head of The Bay.
Is it worth booking a vacation package to Head of The Bay?
Head of The Bay offers everything you need for a wonderful escape. Begin your Head of The Bay vacation on a high note by exploring popular attractions like The Baths.
How to find the best Head of The Bay package deals?
Use Expedia's filter tool to find some tempting Head of The Bay package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Head of The Bay package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Head of The Bay vacation as a package?
You can enjoy significant savings on your Head of The Bay break by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Head of The Bay?
If you're considering a spur-of-the-moment Head of The Bay trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Head of The Bay?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Head of The Bay.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and food to activities and flights. Your hotel will likely be the largest expense during your trip to Head of The Bay.
  3. Decide how long to go for: Now that you're more familiar with Head of The Bay, you can work out the perfect length of your break. Pull together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose a Head of The Bay vacation package that brings all your bookings together.

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.