Anguilla Vacations from $496

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The Latest Anguilla vacation packages

Price found within the past 48 hours. Click for updated prices.
Ruleville Inn By OYO

Ruleville Inn By OYO

2.5 out of 5
Price was $528, price is now $496 per person
$496
per person
Jul 31 - Aug 3
found 18 hours ago
Roundtrip non-stop flight included
Rochester (ROC) to Greenville (GLH)
5.6/10 (56 reviews)
It is quiet. The property is clean.

Reviewed on May 29, 2026

Lyric Hotel West End, Trademark Collection by Wyndham

Lyric Hotel West End, Trademark Collection by Wyndham

3 out of 5
Price was $716, price is now $668 per person
$668
per person
Jul 31 - Aug 3
found 18 hours ago
Roundtrip non-stop flight included
Rochester (ROC) to Greenville (GLH)
8.4/10 Very Good! (209 reviews)
No major complaints. Good stay!

Reviewed on Jun 30, 2026

Red Leaf Cottages

Red Leaf Cottages

3 out of 5
Price was $689, price is now $668 per person
$668
per person
Jul 31 - Aug 3
found 18 hours ago
Roundtrip non-stop flight included
Rochester (ROC) to Greenville (GLH)
9/10 Wonderful! (23 reviews)
Property could have more visible identification of premises from highway and once on grounds

Reviewed on Jun 6, 2026

Turn On Inn

Turn On Inn

3 out of 5
Price was $641, price is now $622 per person
$622
per person
Jul 31 - Aug 3
found 18 hours ago
Roundtrip non-stop flight included
Rochester (ROC) to Greenville (GLH)
9.4/10 Exceptional! (83 reviews)
We alway enjoy our stay very quite a hidden little gem love this place

Reviewed on Jun 28, 2026

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Anguilla Hotel Deals

Rolling Fork Motel

Rolling Fork Motel

2 out of 5
21015 U.S. 61 Rolling Fork MS
$64 nightly
The price is $68 total per night from Jul 3 to Jul 4
$68 total
Jul 3 - Jul 4
Total with taxes and fees
Rolling Fork Motel
X Marks the Spot 3 Bedrooms, 4 Beds, 1 bathroom House. Newly remodeled.

X Marks the Spot 3 Bedrooms, 4 Beds, 1 bathroom House. Newly remodeled.

Hollandale MS
10/10 Exceptional! (1 review)
Very nice!
"So very clean and nice."

Reviewed on Aug 5, 2024

Get rates
X Marks the Spot 3 Bedrooms, 4 Beds, 1 bathroom House. Newly remodeled.
Charming 3-bedroom house with WiFi and AC in Hollandale

Charming 3-bedroom house with WiFi and AC in Hollandale

Hollandale MS
Get rates
Charming 3-bedroom house with WiFi and AC in Hollandale
See all 5 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.

Find the Best Anguilla Vacation Packages

Anguilla Essential Information

Language
English
Currency
U.S dollars
Population
670

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Frequently asked questions

How much does an Anguilla vacation package cost?
You can grab a vacation package to this popular destination from $496 on Expedia. However, how much your vacation to Anguilla costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Anguilla?
September, October and December are great times to search for cheap Anguilla vacation packages. Choosing to travel in quieter months means you can usually find lower prices on hotels and flights.
How many days is enough for Anguilla?
Generally, a handful of days is enough to tick off the top attractions during your Anguilla vacation. But if you'd like to have some time to chill out or go on day tours, think about extending your trip.
How to find the best Anguilla package deals?
Finding a cheap Anguilla package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most affordable Anguilla package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book an Anguilla vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still have the freedom to create a personalized Anguilla vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Anguilla?
Secure fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Anguilla adventure.
Does Expedia offer Book Now, Pay Later Anguilla vacation packages?
If you're anything like us, you love traveling but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Anguilla break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.

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