Windermere Island Cheap Vacations

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Top Cheap vacation packages in Windermere Island

Price found within the past 48 hours. Click for updated prices.
  • Jan 29 - Feb 1

    Daddy Joes + Flight

    Gregory Town
    3 nights
    3.0 star property
    9.6/10 - Exceptional (152 reviews)
    "If you are looking for your home away from home you have found it. Everyone here is like family."
    Reviewed November 8, 2026
    Roundtrip • Boston (BOS) - North Eleuthera (ELH)
    BOS - NAS • Nonstop NAS - BOS • Nonstop
    $630
    $533
    per traveler
    found 1 day ago
    Daddy Joes
  • Jan 29 - Feb 1

    Pink Sands Resort + Flight

    Dunmore Town
    3 nights
    4.0 star property
    8.6/10 - Excellent (128 reviews)
    Roundtrip • Boston (BOS) - North Eleuthera (ELH)
    BOS - NAS • Nonstop NAS - BOS • Nonstop
    Save 100% on your flight
    $2,994
    $2,180
    per traveler
    found 1 day ago
    Pink Sands Resort
  • Dec 18 - Dec 21

    Runaway Hill Inn + Flight

    Dunmore Town
    3 nights
    3.5 star property
    10/10 - Exceptional (1 review)
    "I love Runaway Hill - everyone is extremely accommodating & nice! My room was super comfortable and quiet, spotless. I had to leave a day early, unfortunately, but I can’t wait to return. Yummy Thai food in their restaurant!"
    Reviewed June 24, 2026
    Roundtrip • Boston (BOS) - North Eleuthera (ELH)
    BOS - NAS • Nonstop NAS - BOS • Nonstop
    Save 100% on your flight
    $1,923
    $1,477
    per traveler
    found 15 hours ago
    Runaway Hill Inn
  • Jan 29 - Feb 1

    Romora Bay Resort & Marina + Flight

    Dunmore Town
    3 nights
    3.5 star property
    8.6/10 - Excellent (44 reviews)
    "The marina is very good the food at the restaurant was expensive but taste great We also have a sour experience at the from desk we asked for a water taxi to eluthera airport and they call fo a private taxi without tell us that was private when we got to the island they ask us to pay $70 for the ride that was 10 minutes and for the same ride before they charge us $10 each other than that the experience was nice the beach was very clean and beautiful 😍"
    Reviewed July 26, 2026
    Roundtrip • Boston (BOS) - North Eleuthera (ELH)
    BOS - NAS • Nonstop NAS - BOS • Nonstop
    $1,635
    $1,383
    per traveler
    found 1 day ago
    Romora Bay Resort & Marina
  • Jan 29 - Feb 1

    Tingum Village Hotel + Flight

    Dunmore Town
    3 nights
    3.0 star property
    8.4/10 - Very good (399 reviews)
    Roundtrip • Boston (BOS) - North Eleuthera (ELH)
    BOS - NAS • Nonstop NAS - BOS • Nonstop
    $788
    $694
    per traveler
    found 1 day ago
    Tingum Village Hotel

Discover the most popular places to visit in Windermere Island

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How can I find budget-friendly Windermere Island vacation packages on Expedia?

Playing around with the easy-to-use search wizard is one of the best ways to find affordable Windermere Island vacation packages on Expedia. Tap your dates in and it'll offer some of the cheapest Windermere Island getaways within seconds. You can also use the maximum price filter to view deals within your budget. If you're traveling during peak season dates, it's a good idea to book early to snag some of the best offers. You may score irresistible last-minute specials for travel in low season.

How to find cheap last-minute Windermere Island travel deals?

On Expedia's last-minute travel deals page, you'll encounter a plethora of special offers for late vacations to Windermere Island. Remember, you're more likely to bag savings on last-minute travel during off-peak periods. Consider checking different departure dates, too. Expedia's nifty search tool lets you compare some of the best last-minute Windermere Island vacation packages. The handy filters let you tailor your trip according to your preferences, including hotel star rating, amenities, and property location.

When is the best time to visit Windermere Island on a budget?

For some of the cheapest vacation packages to Windermere Island from $533, it's best to travel during low season dates. With fewer people traveling during these periods, flights and hotels usually have lower prices. It's also a good idea to avoid popular travel times. These include spring break, Thanksgiving, and other federal holidays. On Expedia, you'll encounter some of the best travel deals to Windermere Island. Best of all, vacation payment plans mean you can spread the cost of your trip over 3, 6, or 12 months.

Can I cancel my Windermere Island vacation package booking?

Yes, many of Expedia's cheap Windermere Island getaway packages allow for free cancellation in case your plans change. Follow the easy steps to cancel by logging into your Expedia account and clicking on “Trips” page'. Keep in mind, though, that each vacation package has different cancellation policies, so be sure to look over them before booking. The good news is you'll clearly see this information on Expedia when you book. There's even a free cancellation search filter that lets you view flexible vacations to Windermere Island.

Why should I book my Windermere Island vacation with Expedia?

A multitude of exclusive travel deals you won't find anywhere else is one of the top reasons to book your cheap Windermere Island vacation package with Expedia. And with one of the widest choices of flights and hotels available, you'll easily find the right trip for you. The handy search wizard and filters let you compare hundreds of great deals in seconds, too. It's not only the cheap prices either: Expedia's booking protection and 24/7 support give you peace of mind before and during your 2026 trip.

How to find cheap Windermere Island vacation packages on Expedia?

When searching for budget vacations to Windermere Island, look out for the green savings label. This indicates you've snagged a deal only available on Expedia. Another popular way of getting money off your 2026Windermere Island vacation is by joining One Key. Expedia's amazing reward program gives you access to hundreds of member-only discounts on select hotels. Keep a look out for the blue savings label in the search results. Best of all, One Key is free to join.

Why should I book a package to Windermere Island?

You'll often snag package savings on your Windermere Island vacation when bundling together your flights and accommodation. Expedia even shows you how much you're saving by booking a package. It's not just cheaper prices, either. Packages often have more flexible booking conditions, meaning you're more likely to get a refund in case your 2026 plans change. While booking flights and hotels separately usually requires full payment, Windermere Island vacation packages often let you pay a small upfront deposit to confirm.

How to plan a cheap vacation to Windermere Island?

Settling on your dates is usually the first step to planning an affordable Windermere Island getaway. If you're traveling during peak season dates, it's a good idea to book your trip in advance. This way, you're more likely to bag early-bird deals. Don't rule out a last-minute travel deal for low season dates, though. Once you've picked your dates, tap them into the search wizard to see some of the best Windermere Island vacation package deals. Hop over to Expedia's vacation planning page for more tips for your dream vacation.