The Settlement Trips (flight + hotel)

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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 kilometers 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.

Top hotels in The Settlement

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
9.6/10 Exceptional! (39 reviews)
Saba Rock Resort was so beautiful and Relaxing
"Our experience at Saba Rock Resort was over the top and more than what we expected. Staff was awesome and everyone was welcoming."

Reviewed on Jun 25, 2025

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Saba Rock Resort
See all 76 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.

Frequently asked questions

How much does a The Settlement vacation package cost?
Offering excellent value package deals 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?
You're likely to find reduced prices and better 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?
With a well-organized itinerary, you can easily hit the most popular The Settlement sights in a handful of days. But if you'd like to discover hidden spots or take day trips, think about booking your The Settlement vacation for longer.
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 travelers. Be sure to visit leading sights like Loblolly Bay and Loblolly Bay Beach, and consider renting a car for day trips to explore even more.
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.
How to plan a trip to The Settlement?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit The Settlement.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and dining out to flights and activities. Your hotel will likely be the biggest expense during your trip to The Settlement.
  3. Determine how many days away: Start by compiling a list of the attractions and activities you want to experience in The Settlement. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your airfare and accommodations: Once you've settled on your travel dates and duration, lock in the right The Settlement vacation package for you.

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