Anguilla Vacations from $660

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The Latest Anguilla vacation packages

Price found within the past 48 hours. Click for updated prices.
c towninn and suites

c towninn and suites

2 out of 5
Price was $696, price is now $660 per person
$660
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Greenville (GLH)
5.2/10 (17 reviews)
Red Leaf Cottages

Red Leaf Cottages

3 out of 5
Price was $890, price is now $810 per person
$810
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Greenville (GLH)
9/10 Wonderful! (19 reviews)
I really enjoyed this stay, the place was just as described! Our dog Jazz loved the space to run and play, the views were amazing. The only down side was the road noice, but I think next time I will book the cabin closer to the lake.

Reviewed on May 6, 2026

Turn On Inn

Turn On Inn

3 out of 5
Price was $886, price is now $808 per person
$808
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Greenville (GLH)
9.4/10 Exceptional! (78 reviews)
Something weird happened with our reservation but kind and helpful host upgraded us to a bigger cabin. The floor isn’t level but the cabin was clean and perfectly sufficient for our needs. WiFi didn’t work well for us.

Reviewed on Apr 20, 2026

Cotton House, Cleveland, a Tribute Portfolio Hotel

Cotton House, Cleveland, a Tribute Portfolio Hotel

3.5 out of 5
Price was $999, price is now $913 per person
$913
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Greenville (GLH)
9/10 Wonderful! (659 reviews)
Room was great. Food service on Sunday evening at the hotel restaurant was at best a 2 out of 10. Horrible

Reviewed on May 5, 2026

Lyric Hotel West End, Trademark Collection by Wyndham

Lyric Hotel West End, Trademark Collection by Wyndham

3 out of 5
Price was $997, price is now $920 per person
$920
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Greenville (GLH)
8.2/10 Very Good! (176 reviews)
Clean, modern rooms. Location perfect for Delta State graduation. Very nice pool area and fitness center.

Reviewed on May 8, 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
$59 nightly
The price is $63 total per night from May 10 to May 11
$63 total
May 10 - May 11
Total with taxes and fees
Rolling Fork Motel
Roy's Cabins & Campgrounds

Roy's Cabins & Campgrounds

2 out of 5
7 Roy's Store Rd Hollandale MS
6.8/10 (9 reviews)
The view is great. The cabin is fine. There was a cleaning fee. I was only there 1 night.

Reviewed on Apr 27, 2025

Get rates
Roy's Cabins & Campgrounds
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 4 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 $660 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.