Anguilla Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Anguilla Tourist Board

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 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

Anguilla Holiday

Located in the Eastern Caribbean, Anguilla is a tropical island paradise with crystal clear waters and year-round warm weather. This British territory is famous for its beaches and ecologically significant coral reefs.

Anguilla Hotel + Flights

From the super luxe to the budget friendly, there’s a hotel to suit you here. Options start at NZ$1,511 a night and you have 348 to choose from. Bundle your flights and hotel through Expedia and your credit card will thank you for it. But why stop there? Add options like a tour or dining experience to your Anguilla Holiday Package and you’ll save even more. For a day out you won’t forget, set sail on a classic West Indian sailboat and explore secluded Little Bay.

Your Anguilla Holiday Itinerary

  • Day 1: Most visitors choose to come to Anguilla via Princess Juliana International Airport in nearby St. Maarten. From there, it’s easy to get a sea shuttle, ferry or an air transfer. Freshen up at your hotel after your trip, then head out to see popular sights such as Maundays Bay, Rendezvous Bay and Sandy Island.

  • Day 2: Next, get behind the wheel of your rental car and take a mini road trip on the self-guided Anguilla Heritage Trail. You’ll cruise past historic attractions and learn about the territory’s rich history.

  • Day 3: While you’re in Anguilla, make sure you give your taste buds a treat. With fresh seafood right on your doorstep and some excellent restaurants on the island, you’ll find something to suit every palate.

Anguilla Information

  • Join the locals as they celebrate Anguilla Day on May 30 each year. Festivities are held in the lead up to the day and usually culminate in an awards ceremony in the capital, The Valley.

  • If you want to discover the best of this Caribbean gem, we have you covered. Expedia has Anguilla tours and experiences starting at .

  • Planning to stay in the capital?The Valley Holiday PackagesOpens in a new window is a good place to start looking for great deals.

Our pick of the best Anguilla Hotel Deals

Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Barnes Bay, West End Village
The price is NZ$2,244 per night from 12 Nov to 13 Nov
NZ$2,244
12 Nov - 13 Nov
includes taxes & fees
9.6/10 Exceptional! (237 reviews)
Best place we have been to. The hospitality, staff, food, and the beach was the best. You feel safe in and out of the water lol. The manager David and Chavez made sure all went well. Definitely coming back!

Reviewed on 11 Aug 2025

Four Seasons Resort and Residences Anguilla
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Rendezvous Bay, Rendezvous Bay
The price is NZ$1,511 per night from 1 Dec to 2 Dec
NZ$1,511
1 Dec - 2 Dec
includes taxes & fees
9.6/10 Exceptional! (176 reviews)
Beautiful place, beautiful people! Excellent resort for a family vacation.

Reviewed on 25 Oct 2025

Aurora Anguilla Resort & Golf Club
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Rendezvous Bay, Rendezvous Bay
7.8/10 Good! (254 reviews)
Friendly, breakfast cimplimentary, great beach to swim. Power went out 2x. Once in mid nite, pitch black, could not even see in room

Reviewed on 26 Oct 2025

Get rates
Anguilla Great House Beach Resort
See all 348 properties in Anguilla
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 an Anguilla holiday package cost?
From as low as . Yes, you read that right. Our Anguilla holiday packages are an awesome way to make your budget stretch further. Bundle your favourite hotels, flights and rental car and get to know this top destination.
How do I get a cheap travel package to Anguilla?
It's easy. Just bundle everything together. Flights, hotels and rental cars — combine whatever you need into an Anguilla holiday package to save a ton of cash. Score even more deals when you include extras such as experiences or tours to your booking. But that's not the only good part. You have the flexibility to put together your trip your way. We offer over 550 airlines and 1 000 000 properties throughout the world, so that everyone has a chance to travel and live out those holiday dreams.
What are the top hotels in Anguilla?
For properties in The Valley with friendly service and comfy beds, look up Turtles Nest Beach Resort and Aurora Anguilla Resort & Golf Club. If you plan to visit West End Village as well, you'll get a wonderful night's sleep at Anguilla Great House Beach Resort or Four Seasons Resort and Residences Anguilla.
How far in advance should I book my Anguilla holiday?
Reserving your flight early with Expedia means one less thing to worry about. A number of air carriers display prices up to 12 months prior to departure dates. This is often the cheapest time to book. If circumstances have left you booking late, last-minute deals to Anguilla sometimes emerge a few weeks before departure.
What does an Expedia Anguilla travel package include?
It all depends on what type of getaway you're planning. Anguilla holiday deals can include car rentals, flights and hotels. You can mix and match to create the bundle that suits your budget and style. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking an Anguilla travel package?
A travel package can be easier on the hip pocket than individually booking everything you need for your trip. For example, bundle your hotels, flights and rental cars and save a pretty penny. No matter your holiday plans, there's sure to be a package that's perfect for you.
Can I choose my airline with an Anguilla Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You're the boss! We have more than 550 partner airlines throughout the world, so you have loads of choice when putting together your Anguilla getaway.
If I'm not able to travel, can I cancel my Anguilla holiday package?
Plans can change in a flash, so yes. You may be able to change or cancel your Anguilla holiday package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still make changes, but your airline, hotel or car rental company may impose a charge. Looking for more information? Have a look at our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Anguilla

Meads Bay

Meads Bay

Commune with nature and explore the great outdoors at Meads Bay during your travels in West End Village. Amble around this relaxing area's beautiful beaches and enjoy its top-notch restaurants.

Meads Bay
Rendezvous Bay Beach

Rendezvous Bay Beach

Why not spend a care-free afternoon at Rendezvous Bay Beach during your travels in Rendezvous Bay? While in the area, you can find time to visit its spas.

Rendezvous Bay Beach

What to do in Anguilla

Sightseeing Tour of the French and Dutch Sides of the Island

St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island

NZ$97
per adult
82% of travellers recommend
St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

NZ$148
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
Amazing Plane Spotting at Maho Beach

Amazing Plane Spotting at Maho Beach

NZ$46
per adult
Amazing Plane Spotting at Maho Beach
See all activities in Anguilla
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.