Windermere Island Adventure Vacations

Book a Adventure Hotel + Flight or Car together to unlock savings

Top Adventure vacation packages in Windermere Island

Price found within the past 48 hours. Click for updated prices.

The Cove Eleuthera

Save 100% on your flight

$2,311

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

9.2/10 Wonderful! (250 reviews)

The Cove feels like your own tropical island. Very quiet and the food at the restaurant was fresh and delicious. If you’re looking to get away and truly relax in the peaceful Caribbean, The Cove is your place!

Reviewed on Jul 23, 2025

Valentines Resort & Marina

Save 100% on your flight

$5,231

per person

Dec 26 - Jan 2

found 12 hours ago

Roundtrip flight included

Boston (BOS) to North Eleuthera (ELH)

8.8/10 Excellent! (222 reviews)

4th year, of 5 day stays, 4 months in a row, staying at Valentines Resort and Marina. Location and amenities were a strong 4 star in the beginning. But each year has gotten worse. Room maintenance has deteriorated but worse has been the staff and dining / bar area. Quality and speed of service and food has gotten horrible. Seems to be plenty of wait staff available but little desire to be attentive or diligent in their duties. Meanwhile menu choices have reduced and quality of food preparation has declined. Food / bar quality and service is a huge part of any resorts amenities. This decline can only be laid on management. It is a shame to see this decline as Valentines was a great experience all around. And could be again.

Reviewed on Jun 16, 2025

Pink Sands Resort

$3,282

per person

Nov 28 - Dec 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

8.6/10 Excellent! (119 reviews)

Very private and stunning beach!

Reviewed on Mar 16, 2025

Coral Sands Inn & Cottages

$3,555

per person

Nov 28 - Dec 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

9.2/10 Wonderful! (349 reviews)

The pink sand beach and sunrise is breathtaking. The staff is thoughtful and very accommodating.

Reviewed on Jul 24, 2025

Don't see what you're looking for?

See all available trips from Columbus to Windermere Island

View all trips

3 Night Adventure vacations in Windermere Island

Price found within the past 48 hours. Click for updated prices.

Valentines Resort & Marina

$1,584

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

8.8/10 Excellent! (222 reviews)

4th year, of 5 day stays, 4 months in a row, staying at Valentines Resort and Marina. Location and amenities were a strong 4 star in the beginning. But each year has gotten worse. Room maintenance has deteriorated but worse has been the staff and dining / bar area. Quality and speed of service and food has gotten horrible. Seems to be plenty of wait staff available but little desire to be attentive or diligent in their duties. Meanwhile menu choices have reduced and quality of food preparation has declined. Food / bar quality and service is a huge part of any resorts amenities. This decline can only be laid on management. It is a shame to see this decline as Valentines was a great experience all around. And could be again.

Reviewed on Jun 16, 2025

The Cove Eleuthera

Save 100% on your flight

$2,311

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

9.2/10 Wonderful! (250 reviews)

The Cove feels like your own tropical island. Very quiet and the food at the restaurant was fresh and delicious. If you’re looking to get away and truly relax in the peaceful Caribbean, The Cove is your place!

Reviewed on Jul 23, 2025

Pink Sands Resort

$2,472

per person

Dec 12 - Dec 15

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

8.6/10 Excellent! (119 reviews)

Very private and stunning beach!

Reviewed on Mar 16, 2025

Don't see what you're looking for?

See all available trips from Columbus to Windermere Island

View all trips

4 Night Adventure vacations in Windermere Island

Price found within the past 48 hours. Click for updated prices.

Daddy Joes

$750

per person

Jan 2 - Jan 6

found 1 day ago

Roundtrip flight included

New York (JFK) to North Eleuthera (ELH)

9.6/10 Exceptional! (125 reviews)

Property is across the street from mind-blowingly beautiful beach. Owners were welcoming and communicative about car rental, etc and food at the restaurant is great

Reviewed on Aug 3, 2025

Tingum Village Hotel

$998

per person

Nov 28 - Dec 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

8.4/10 Very Good! (339 reviews)

This is a gem , clean room , friendly staff. Juanita have all your needs ,she has contact for everything in Harbour island and Eleuthera. We stayed off season and she made sure we had everything we needed during our stay. Nice on site restaurant as well! Can’t go wrong!

Reviewed on Sep 1, 2025

Valentines Resort & Marina

Save 100% on your flight

$2,165

per person

Jan 2 - Jan 6

found 1 day ago

Roundtrip flight included

New York (JFK) to North Eleuthera (ELH)

8.8/10 Excellent! (222 reviews)

4th year, of 5 day stays, 4 months in a row, staying at Valentines Resort and Marina. Location and amenities were a strong 4 star in the beginning. But each year has gotten worse. Room maintenance has deteriorated but worse has been the staff and dining / bar area. Quality and speed of service and food has gotten horrible. Seems to be plenty of wait staff available but little desire to be attentive or diligent in their duties. Meanwhile menu choices have reduced and quality of food preparation has declined. Food / bar quality and service is a huge part of any resorts amenities. This decline can only be laid on management. It is a shame to see this decline as Valentines was a great experience all around. And could be again.

Reviewed on Jun 16, 2025

Don't see what you're looking for?

See all available trips from Columbus to Windermere Island

View all trips

How can I book the best Windermere Island adventure trips?

Choose your own adventure in Windermere Island, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.

How can I plan the perfect Windermere Island family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Windermere Island. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.

Can I book all-inclusive Windermere Island adventure vacation packages?

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.

Why should I book a Windermere Island adventure vacation for couples?

Book a Windermere Island couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

How can I find the best deals on adventure packages in Windermere Island?

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.

Can I book an adventure vacation package in Windermere Island with free cancellation and/or flexible dates?

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.