The Settlement Holidays

Book a Hotel + Flight or Car together to unlock savings

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
9.6/10 Exceptional! (42 reviews)
"I went with my husban and we loved EVERYTHING. The service, the cleanliness, the room, the views… in short EVERYTHING. We had a great time. We’ll be back 😉"

Reviewed on 1 Aug 2025

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Saba Rock Resort
See all 75 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 holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday packages and you could land some excellent off-season deals.
How many days is enough for The Settlement?
With a well-organised 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 holiday for longer.
Is it worth booking a holiday package to The Settlement?
Popular for its watersports, history and culture, a The Settlement holiday is a hit with all kinds of travellers. 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 holiday package as soon as possible.
Is it cheaper to book a The Settlement holiday as a package?
An Expedia holiday 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 holiday 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 accommodation: Once you've settled on your travel dates and duration, lock in the right The Settlement holiday package for you.