The Settlement Vacations from $2,009

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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.

The Latest The Settlement vacation packages

Price found within the past 48 hours. Click for updated prices.
Scrub Island Resort, Spa & Marina

Scrub Island Resort, Spa & Marina

5 out of 5
Save 100% on your flight
Price was $3,115, price is now $2,009 per person
$2,009
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tortola (EIS)
9.2/10 Wonderful! (174 reviews)
Excellent staff and room

Reviewed on Nov 4, 2025

Bitter End Yacht Club

Bitter End Yacht Club

3.5 out of 5
Price was $12,263, price is now $4,948 per person
$4,948
per person
Feb 14 - Feb 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tortola (EIS)
9/10 Wonderful! (46 reviews)
it was amazing; the spot the beaches, the staff, the wifi and the activities are out of this world.

Reviewed on Jul 12, 2017

The Aerial, BVI

The Aerial, BVI

4 out of 5
Save 100% on your flight
Price was $4,899, price is now $3,183 per person
$3,183
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tortola (EIS)
9.6/10 Exceptional! (4 reviews)
Our stay at the Aerial BVI was exceptional. The property is breathtaking, the staff is so kind and cater to your every need. The island has such a special purpose and meaning behind it bad we were so happy to experience it. We took advantage of the horseback riding, spa treatments, night glass bottom kayak ride. The food was all farm to table and healthy and the beach was beautiful. I can’t say enough about the room design and the stunning ocean views. This property is one of a kind and a rare gem. Every detail is so thought out and the focus is on healing and wellness which I love. We will definitely be back and have already told all of our loved ones.

Reviewed on Jul 9, 2024

Cane Garden Bay Beach Hotel

Cane Garden Bay Beach Hotel

3.5 out of 5
Price was $4,292, price is now $3,193 per person
$3,193
per person
Feb 14 - Feb 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tortola (EIS)
9.8/10 Exceptional! (169 reviews)
Excellent staff and beautiful room.

Reviewed on Nov 4, 2025

Saba Rock Resort

Saba Rock Resort

3.5 out of 5
Price was $5,835, price is now $4,457 per person
$4,457
per person
Feb 14 - Feb 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tortola (EIS)
9.8/10 Exceptional! (44 reviews)
Amazing location, atmosphere and staff. We come 2x a year and look forward to it so much!

Reviewed on Nov 26, 2025

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Discover the most popular places to visit in The Settlement

Loblolly Bay Beach

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.

Loblolly Bay Beach

The Settlement Hotel Deals

Sea Grape Villas

Sea Grape Villas

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

Four Diamonds Park Villas

3.5 out of 5
Anegada The Settlement Anegada
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Four Diamonds Park Villas
Saba Rock Resort

Saba Rock Resort

3.5 out of 5
North Sound Saba Rock
Fully refundableReserve now, pay when you stay
$356 nightly
The price is $389 total per night from Dec 9 to Dec 10
$389 total
Dec 9 - Dec 10
Total with taxes and fees
9.6/10 Exceptional! (46 reviews)
Amazing location, atmosphere and staff. We come 2x a year and look forward to it so much!

Reviewed on Nov 26, 2025

Saba Rock Resort
See all 71 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.

Find the Best The Settlement Vacation Packages

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 1 mile (2 km) 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.

The Settlement Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Terrance B. Lettsome Intl. Airport (EIS)
Max Temp Winter
80ºF
Max Temp Summer
85ºF
Top Sights
Loblolly Bay Beach and Loblolly Bay

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Frequently asked questions

How much does a The Settlement vacation package cost?
Offering excellent value package deals from $2,009 on Expedia, you'll be thrilled with how little a vacation to The Settlement costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to The Settlement?
If you're looking to snag a cheap The Settlement vacation package, consider planning a trip in January, May and September. You'll typically find lower rates on hotels and airfares during these months — ideal for travelers wishing to save money.
How many days is enough for The Settlement?
The ideal length of your The Settlement vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you time to hit all the main attractions and explore some hidden gems along the way.
Is it worth booking a vacation package to The Settlement?
It's no wonder a The Settlement vacation is on the to-do list of many travelers. Top attractions like Loblolly Bay Beach are just the beginning of things to see and do here.
How to find the best The Settlement package deals?
Use Expedia's filters to help you find some terrific The Settlement package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for The Settlement package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a The Settlement vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and hotels separately. Better still, you can tailor your The Settlement trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to The Settlement?
Score incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu The Settlement getaway.
Does Expedia offer Book Now, Pay Later The Settlement vacation packages?
Jet off on your dream getaway to The Settlement with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for your next paycheck — 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 over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stick to your budget and snag great deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.