The Settlement Vacation Packages

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Your The Settlement Vacation

When you choose a The Settlement vacation package, you can really enjoy your adventure to the fullest. Uncover the best parts of this fascinating city knowing that all your travel needs have been looked after before you go. Make sure to do some sightseeing during your trip to The Settlement. Loblolly Bay Beach and Loblolly Bay are some of the major places to check out. That dream The Settlement vacation is just clicks away. Search accommodations, flights and more on Expedia for a trip that's tailored to suit your travel style.

Top The Settlement Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Village Cay Hotel and Marina

Village Cay Hotel and Marina

3.5 out of 5
Wickhams Cay 1
Price was CA $1,816, price is now CA $1,460 per person
CA $1,460
per person
Oct 5 - Oct 12
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Tortola (EIS)
8.2/10 Very good! (994 reviews)

Scrub Island Resort, Spa & Marina

Scrub Island Resort, Spa & Marina

5 out of 5
Price was CA $2,907, price is now CA $2,320 per person
CA $2,320
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tortola (EIS)
9/10 Wonderful! (193 reviews)
Everything went spectacular

Reviewed on Jul 7, 2026

Saba Rock Resort

Saba Rock Resort

3.5 out of 5
Price was CA $8,942, price is now CA $7,163 per person
CA $7,163
per person
Oct 5 - Oct 12
found 3 hours ago
Roundtrip flight included
Montreal (YMQ) to Tortola (EIS)
9.8/10 Exceptional! (63 reviews)
They don’t bring alcohol to your room. Otherwise spitting image of perfect

Reviewed on Jun 17, 2026

The Aerial, BVI

The Aerial, BVI

4 out of 5
Price was CA $13,076, price is now CA $10,574 per person
CA $10,574
per person
Oct 5 - Oct 12
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Tortola (EIS)
9/10 Wonderful! (6 reviews)
Stunning. The most relaxing hotel I've ever stayed at. Food was incredible, but pricey, skid the starters (cheaper to order a 2nd entree if you're hungry). Absolutely incredible stay! We stayed in late February and the breeze was incredible. The staff was amazing, the rooms were incredible but only lock from the inside (and they have a safe in each room) I actually loved that I didn't have to worry about a key, and because every room is like that, no one will rob you because everyone's room is that, feels like a great honor system, plus for the price per night, it's not attracting people who steal. The views are incredible, such a peaceful and healing private island. The showers, WOW, the most iconic high end outdoor showers I've ever experienced (we got to try 2 very different rooms). Two gyms, one indoor with an ocean view, one outdoor jungle gym style.

Reviewed on Jun 2, 2026

The Lighthouse Villas

The Lighthouse Villas

3.5 out of 5
Price was CA $1,781, price is now CA $1,476 per person
CA $1,476
per person
Oct 5 - Oct 12
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Tortola (EIS)
9/10 Wonderful! (199 reviews)
Nice room. Simone was great and very accommodating

Reviewed on Jun 15, 2026

The Settlement Beach Vacation

Get prepared to live out those beachy daydreams on your The Settlement vacation. Go on a leisurely walk, soak up the gorgeous coastal vistas and collect unique seashells during your trip to The Settlement. Just 2 kilometres from the center of town, Loblolly Bay Beach is the place to be for many travelers. Have a look through our The Settlement vacation deals and watch your travel budget stretch further!

Things You Should Know About The Settlement

  • If your idea of the perfect vacation includes staying within walking distance of the shoreline, the scent of salty air drifting through your window and crashing waves lulling you to sleep, browse our The Settlement beach hotels.
  • Another style of place to stay is villas. Check out Sea Grape Villas and Four Diamonds Park Villas and compare the prices and amenities.

Ready to book your vacation to The Settlement?

 

Choose your dates

The Settlement Hotel Deals

Four Diamonds Park Villas

Four Diamonds Park Villas

3.5 out of 5
Anegada The Settlement Anegada
Get rates
Four Diamonds Park Villas
Sea Grape Villas

Sea Grape Villas

3.5 out of 5
The Settlement The Settlement Anegada Island
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Sea Grape Villas
Saba Rock Resort

Saba Rock Resort

3.5 out of 5
North Sound Saba Rock
The price is CA $533 per night from Aug 3 to Aug 4
CA $533
CA $641 total
Aug 3 - Aug 4
includes taxes & fees
9.8/10 Exceptional! (64 reviews)
"They don’t bring alcohol to your room. Otherwise spitting image of perfect"

Reviewed on Jun 17, 2026

Saba Rock Resort
See all 72 properties in The Settlement
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

Stay near popular The Settlement attractions

Loblolly Bay Beach

10.0/10 (2 reviews)
Why not spend a carefree afternoon at Loblolly Bay Beach during your travels in The Settlement? While you're in the area, stroll along the seaside.
See properties

Frequently asked questions

How much does a The Settlement vacation package cost?
You'll find cheap prices from CA $1,460 on Expedia for your The Settlement break. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to The Settlement costs.
What are the cheapest months to go to The Settlement?
You can usually find reduced prices and greater availability in August, September and October. Browse our cheap The Settlement vacation packages and you could land some excellent off-season deals.
How many days is enough for The Settlement?
Typically, a handful of days is enough to see the top sights during your The Settlement vacation. But if you prefer to have some time to kick back or take day trips, think about extending your trip.
Is it worth booking a vacation package to The Settlement?
Popular for its watersports, history and culture, a The Settlement vacation is a hit with all kinds of travellers. Be sure to check out major sights like Loblolly Bay and Loblolly Bay Beach, and consider renting a set of wheels for day trips to explore even more.
How to find the best The Settlement package deals?
Begin your search for a The Settlement package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect The Settlement package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your The Settlement escape underway.
Is it cheaper to book a The Settlement vacation as a package?
You can enjoy significant savings on your The Settlement retreat by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to The Settlement?
If you've got your The Settlement travel dates confirmed, book as early as you can to grab some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to The Settlement?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to The Settlement.
  2. Set a budget: Consider expenses such as flights, transportation and food when calculating how much to save for your trip to The Settlement. Then, select a hotel that matches your budget, whether that's a low-cost stay or a deluxe getaway.
  3. Decide your trip length: Consider how long you'd like to spend discovering The Settlement. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a The Settlement vacation package that brings all your bookings together.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.