A poolside area with lounge chairs, palm trees, and a view of the ocean.
Photo by Anguilla Tourist Board
Open Photo by Anguilla Tourist Board

The Quarter Vacations from $2,337

Book a Hotel + Flight or Car together to unlock savings

The Latest The Quarter Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Oct 17 - Oct 20

    Four Seasons Resort and Residences Anguilla + Flight

    West End Village
    3 nights
    5.0 star property
    9.8/10 - Exceptional (259 reviews)
    "I love the four seasons in Anguilla!! This is my 3rd time going to the island and I wouldn't stay anywhere else!’Nothing but top notch service!! Amazing time!!"
    Reviewed July 28, 2026
    Roundtrip New York (EWR) - The Valley (AXA)
    EWR - AXA1 stop AXA - EWR3 stops
    $2,644
    $2,337
    per traveler
    found 1 day ago
    Four Seasons Resort and Residences Anguilla
  • Oct 22 - Oct 27

    Malliouhana Resort Anguilla + Flight

    West End Village
    5 nights
    5.0 star property
    9.6/10 - Exceptional (103 reviews)
    "Amazing"
    Reviewed July 23, 2026
    Roundtrip New York (EWR) - The Valley (AXA)
    EWR - AXA2 stops AXA - EWR1 stop
    $4,067
    $3,365
    per traveler
    found 13 hours ago
    Malliouhana Resort Anguilla
  • Oct 17 - Oct 20

    Aurora Anguilla Resort & Golf Club + Flight

    Rendezvous Bay
    3 nights
    5.0 star property
    9.6/10 - Exceptional (202 reviews)
    "Asian restaurant hostess was rude."
    Reviewed July 16, 2026
    Roundtrip New York (EWR) - The Valley (AXA)
    EWR - AXA1 stop AXA - EWR3 stops
    $3,418
    $2,860
    per traveler
    found 1 day ago
    Aurora Anguilla Resort & Golf Club
  • Oct 1 - Oct 6

    6 BR Villa On Crocus Bay With Pool Concierge + Flight

    The Valley
    5 nights
    2.0 star property
    Roundtrip Boston (BOS) - The Valley (AXA)
    BOS - AXA2 stops AXA - BOS2 stops
    $7,596
    $6,521
    per traveler
    found 23 hours ago
    6 BR Villa On Crocus Bay With Pool Concierge
  • Oct 1 - Oct 6

    6 BR Villa With Concierge Amenities Pool + Flight

    The Valley
    5 nights
    2.0 star property
    Roundtrip Boston (BOS) - The Valley (AXA)
    BOS - AXA2 stops AXA - BOS2 stops
    $7,596
    $6,521
    per traveler
    found 23 hours ago
    6 BR Villa With Concierge Amenities Pool

What to do in The Quarter

The Quarter Hotel Deals

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 Quarter vacation package cost?

You'll find cheap prices from $2,337 on Expedia for your The Quarter escape. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to The Quarter costs.

What are the cheapest months to go to The Quarter?

July, August and December are great times to look for cheap The Quarter vacation packages. Opting to travel in less busy months means you can generally find lower prices on hotels and flights.

How many days is enough for The Quarter?

Typically, a handful of days is enough to visit the main sights during your The Quarter vacation. But if you prefer to have time to relax or take day trips, consider extending your itinerary.

How to find the best The Quarter package deals?

Begin your search for a The Quarter package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect The Quarter package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your The Quarter escape off to a flying start.

Is it cheaper to book a The Quarter vacation as a package?

Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component individually. And you'll still have the flexibility to create a personalized The Quarter vacation by choosing your favorite type of stay, airline and car class.

When to book a vacation package to The Quarter?

Enjoy incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment The Quarter escape.

How to plan a trip to The Quarter?

  1. Pick the best time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to go to The Quarter.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your accommodations will likely be the largest expense during your trip to The Quarter.
  3. Use our trip planning tool to discover The Quarter: Research every part of your trip to The Quarter with this handy planner. Invite your friends and family to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Set the duration of your trip: Start by listing all the attractions you'd like to get to in The Quarter. Then, estimate how long you'll need for each, along with any travel time.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a The Quarter vacation package that brings all your bookings together.
  6. Book experiences or activities ahead of time: Whether it's entrance to a major attraction or a day trip in nature, you won't have to worry about missing out on the best The Quarter has to offer. Find all the incredible things to do in The Quarter in The Quarter with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later The Quarter vacation packages?

If you're like us, you love traveling the world but are not a fan of the big 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 spread the total cost of your The Quarter trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.

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