Anguilla Vacations from $397

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The Latest Anguilla vacation packages

Price found within the past 48 hours. Click for updated prices.
Dreamland Inn and Suites

Dreamland Inn and Suites

$397
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Greenville (GLH)
7/10 Good! (64 reviews)
Clean rooms, great customer service

Reviewed on Aug 13, 2026

Ruleville Inn By OYO

Ruleville Inn By OYO

$1,139
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Greenville (GLH)
5.6/10 (56 reviews)
It is quiet. The property is clean.

Reviewed on May 29, 2026

Southern Inn Lake Village Near Greenville MS 1

Southern Inn Lake Village Near Greenville MS 1

$657
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Greenville (GLH)
2/10 (3 reviews)
Address was wrong never found hotel still got charged

Reviewed on Aug 10, 2026

Turn On Inn

Turn On Inn

$821
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Greenville (GLH)
9.6/10 Exceptional! (91 reviews)
Red Leaf Cottages

Red Leaf Cottages

$821
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Greenville (GLH)
9/10 Wonderful! (25 reviews)
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Anguilla Hotel Deals

Rolling Fork Motel

Rolling Fork Motel

21015 U.S. 61 Rolling Fork MS
$34 nightly
$36 total
Aug 17 - Aug 18
Total with taxes and fees
5.6/10 (20 reviews)
"The air conditioner control unit didn’t work the room wasn’t as clean as it should be no rails to hold on to get in the bathtub knob will come off the tallest seat but very small not good if you have handicap issues and I had handicap issues so it was not comfortable for me at all. It said handicap ..."

Reviewed on Aug 13, 2026

Rolling Fork Motel
4-bedroom house in welcoming Mayersville with cool AC

4-bedroom house in welcoming Mayersville with cool AC

Mayersville MS
$251 nightly
$268 total
Sep 15 - Sep 16
Total with taxes and fees
4-bedroom house in welcoming Mayersville with cool AC
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! (2 reviews)
"I stay here 2 times a year for business reasons. This home is always spotless and well maintained. It is a very quiet safe neighborhood."

Reviewed on Jul 15, 2026

Get rates
X Marks the Spot 3 Bedrooms, 4 Beds, 1 bathroom House. Newly remodeled.
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 $397 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.