Road Town Vacations from $1,261

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Your Road Town Vacation

Say farewell to planning worries and hello to a Road Town vacation package. With the finer details organized before you take off, you can focus on discovering every inch of this city, starting with Wickhams Cay 1, which is good for views, dining and shopping. Make your trip to Road Town even more fun by including some sightseeing. Cane Garden Bay Beach, Anegada Island and Nanny Cay are some of the popular attractions worth exploring. Browse Expedia's wide range of travel options and start organizing your ideal vacation to Road Town today.

The Latest Road Town vacation packages

Price found within the past 48 hours. Click for updated prices.
The Lighthouse Villas

The Lighthouse Villas

3.5 out of 5
Price was $1,410, price is now $1,261 per person
$1,261
per person
Aug 26 - Aug 31
found 10 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Tortola (EIS)
9/10 Wonderful! (198 reviews)
Nice room. Simone was great and very accommodating

Reviewed on Jun 15, 2026

Long Bay Beach Resort

Long Bay Beach Resort

4.5 out of 5
Price was $2,813, price is now $2,247 per person
$2,247
per person
Aug 26 - Aug 31
found 10 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Tortola (EIS)
9.2/10 Wonderful! (208 reviews)
Stunning beach and rooms, great drinks and food! Super remote area, great if you want to feel off the grid

Reviewed on May 27, 2026

Coconut Tree Villa

Coconut Tree Villa

3.5 out of 5
Price was $2,684, price is now $2,212 per person
$2,212
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tortola (EIS)
8.6/10 Excellent! (40 reviews)
Great location near airport !!

Reviewed on Mar 10, 2026

White Bay Villas and Beach Club

White Bay Villas and Beach Club

4 out of 5
Price was $2,439, price is now $2,015 per person
$2,015
per person
Aug 26 - Aug 31
found 10 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Tortola (EIS)
9.6/10 Exceptional! (35 reviews)
Our stay at White Bay Villas was perfection. We were able to contact the managers at any time when we needed things, they were helpful with our luggage, calling taxis, getting to the ferry, and answering any questions we had. The villa was clean with perfect views of the beach, which was within walking distance down the hill. We loved every minute and will definitely be back.

Reviewed on Feb 1, 2026

Saba Rock Resort

Saba Rock Resort

3.5 out of 5
Price was $2,146, price is now $1,848 per person
$1,848
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Tortola (EIS)
9.8/10 Exceptional! (62 reviews)
They don’t bring alcohol to your room. Otherwise spitting image of perfect

Reviewed on Jun 17, 2026

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Where to stay in Road Town

Find the best Road Town areas and neighborhoods for the activities you enjoy most. Learn more about Road Town
Waterfront

Waterfront

2 out of top 10 points of interest in this area
3.5/5(25 area reviews)

If you're spending some time in Waterfront, Government House and Main Street are top sights worth seeing.

Find hotels in Waterfront

Discover the most popular places to visit in Road Town

Trunk Bay Beach, St John, Virgin Islands National Park, Caribbean

Trunk Bay Beach

If a restful vacation is part of your travel plans, Trunk Bay Beach might be the perfect place to seek out during your trip to Road Town. Stroll along the seaside or seek out the sailing opportunities.

Trunk Bay Beach
An aerial view of a narrow island with clear turquoise waters and a sandy beach.

Anegada Island

Commune with nature and explore the great outdoors at Anegada Island during your travels in Road Town. Wander the beautiful beaches and seaside in this romantic area.

Anegada Island

Tortola Cruise Ship Port

Explore the waterfront in Road Town with a trip to Tortola Cruise Ship Port. Wander the beautiful beaches and seaside in this romantic area.

Tortola Cruise Ship Port

What to do in Road Town

St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton

St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton

$319
per adult
St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton
Romantic

St. Thomas Dinner Sail to St. John with Open Bar & Hors D'oeuvres - Ritz-Carlton

$149
per adult
88% of travellers recommend
St. Thomas Dinner Sail to St. John with Open Bar & Hors D'oeuvres - Ritz-Carlton
US Virgin Islands Island Hop & Food Boat Tour

US Virgin Islands Island Hop & Food Boat Tour

$350
per adult
80% of travellers recommend
US Virgin Islands Island Hop & Food Boat Tour
See all activities in Road Town

Road Town Hotel Deals

Nanny Cay Resort and Marina

Nanny Cay Resort and Marina

3 out of 5
Nanny Cay Road Town NA
$209 nightly
The price is $229 total per night from Jun 29 to Jun 30
$229 total
Jun 29 - Jun 30
Total with taxes and fees
9.4/10 Exceptional! (225 reviews)
"Location"

Reviewed on Jun 21, 2026

Nanny Cay Resort and Marina
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
$175 nightly
The price is $191 total per night from Jun 22 to Jun 23
$191 total
Jun 22 - Jun 23
Total with taxes and fees
8.2/10 Very Good! (988 reviews)
"The rooms were clean, housekeeping was on the ball with linens and towels. The staff was cheerful. The facilities are just getting old and a bit run down. The pool looked like it needed tile work done. Overall a good value for the price, but I will upgrade to a better resort next time. It is not ..."

Reviewed on Jun 18, 2026

Village Cay Hotel and Marina
Maria's By the Sea Hotel

Maria's By the Sea Hotel

3.5 out of 5
Road Town Road Town Tortola
$232 nightly
The price is $254 total per night from Jun 22 to Jun 23
$254 total
Jun 22 - Jun 23
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Friendly staff"

Reviewed on Jun 17, 2026

Maria's By the Sea Hotel
See all 660 properties in Road Town
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 Road Town Vacation Packages

Road Town Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Terrance B. Lettsome Intl. Airport (EIS)
Population
8,400
Max Temp Winter
80ºF
Max Temp Summer
85ºF
Top Sights
Smugglers Cove Beach, Cane Garden Bay Beach and Long Bay Beach

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Frequently asked questions

How much does a Road Town vacation package cost?
You'll find cheap prices from $1,261 on Expedia for your Road Town escape. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Road Town costs.
What are the cheapest months to go to Road Town?
If you're looking to book a cheap Road Town vacation package, consider visiting in May, June and December. You're likely to find lower prices on hotels and airfares during these months — perfect for travelers wishing to save money.
How many days is enough for Road Town?
With around 2 days, you'll have enough time to experience popular neighborhoods such as Waterfront and Wickhams Cay 1 during your Road Town vacation. Remember to also add Biras Creek Trail and Road Town Methodist Church to your sightseeing list. Looking for more adventures? Consider exploring outside of Road Town on tours and day trips.
Is it worth booking a vacation package to Road Town?
Whether you want to explore attractions like Nanny Cay and Anegada Island on your Road Town vacation, or coming for its great nature, shopping and gift and craft shops, there's something for everyone here. With so much to experience, you'll soon find out why so many people think Road Town is a good vacation destination.
How to find the best Road Town package deals?
Use Expedia's handy filters to find some of the best Road Town package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Road Town package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Road Town vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and stays individually. Better still, you can personalize your Road Town escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Road Town?
If you've got your Road Town travel dates confirmed, book as early as you can to bag some outstanding deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Road Town?

  1. Choose when to get away: Check your calendar and pack your bags. Your favorite season and the activities on offer will also help you decide when to vacation in Road Town.
  2. Set your budget: Factor in costs such as flights, meals and transportation when calculating how much to put aside for your trip to Road Town. Then, select a property that suits your budget, whether that's a wallet-friendly stay or a deluxe retreat.
  3. Discover Road Town using Expedia's trip planning tool: Gain insights into the top attractions and best properties for your trip to Road Town. You can also save your must-visit places, collaborate with friends and family and manage your plans in one place.
  4. Decide how long to go for: Now that you're up to speed on Road Town, you can work out the right length of your vacation. Pull together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Road Town vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Read our dedicated travel guide to find some exciting things to do in Road Town. Book tickets or make reservations as soon as you can to save time and avoid the hassle of trying to find activities once you arrive.

Does Expedia offer Book Now, Pay Later Road Town vacation packages?
Secure your dream getaway to Road Town with our Book Now, Pay Later vacations. No need to save up or hold off until payday — we've joined forces with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stay on budget and snap up bargains before they disappear.

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.