The Settlement Vacations from $2,552

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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 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
Price was $3,412, price is now $2,552 per person
$2,552
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tortola (EIS)
9.2/10 Wonderful! (174 reviews)
Staff were very friendly. Views are stunning. Delightful resort.

Reviewed on Jan 30, 2026

Saba Rock Resort

Saba Rock Resort

3.5 out of 5
Save 100% on your flight
Price was $9,139, price is now $6,905 per person
$6,905
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tortola (EIS)
9.8/10 Exceptional! (44 reviews)
Lovely clean and comfortable room

Reviewed on Feb 23, 2026

Cane Garden Bay Beach Hotel

Cane Garden Bay Beach Hotel

3.5 out of 5
Price was $3,942, price is now $3,055 per person
$3,055
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tortola (EIS)
9.8/10 Exceptional! (169 reviews)
Everything was too notch from the pre-stay contact by the staff on airport transfers, to the room, coordination of activities and taxis to great food and beach bar. Loved the stay and can’t say enough good things. Thanks.

Reviewed on Feb 20, 2026

Bitter End Yacht Club

Bitter End Yacht Club

3.5 out of 5
Price was $4,988, price is now $3,880 per person
$3,880
per person
May 20 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tortola (EIS)
9/10 Wonderful! (46 reviews)
Great staff and facilities

Reviewed on Feb 13, 2026

Rosewood Little Dix Bay

Rosewood Little Dix Bay

5 out of 5
Save 100% on your flight
Price was $11,365, price is now $9,366 per person
$9,366
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tortola (EIS)
9.2/10 Wonderful! (95 reviews)
The butler service was fantastic. The food and drinks were great! Everyone was friendly and helpful. It was a second honeymoon for us and they gave us a bottle of champagne and a yummy dessert. My only complaint is that everything was very pricey.

Reviewed on Nov 12, 2025

Don't see what you're looking for?
See all available trips from Columbus to The Settlement
View all trips

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

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

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
Get rates
Sea Grape Villas
Saba Rock Resort

Saba Rock Resort

3.5 out of 5
North Sound Saba Rock
Fully refundableReserve now, pay when you stay
9.8/10 Exceptional! (53 reviews)
Lovely clean and comfortable room

Reviewed on Feb 23, 2026

Get rates
Saba Rock Resort
See all 73 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a The Settlement vacation package cost?
Offering excellent value package deals from $2,552 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.