Chesters Vacations from $748

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Your Chesters Vacation

Our Chesters vacation packages offer endless opportunities to discover new sights, sounds and sensations. And with all the planning taken care of, you can chill out and enjoy your city escape just like you deserve. Devils Backbone is just one of the big-ticket attractions to include on your itinerary during a trip to Chesters. Don't put off visiting this destination any longer. Your dream Chesters vacation is a few quick clicks away with Expedia.

The Latest Chesters vacation packages

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

Sky Beach Club

4 out of 5
Price was $1,075, price is now $748 per person
$748
per person
Aug 9 - Aug 13
found 2 days ago
Roundtrip non-stop flight included
Dallas (DFW) to Governor's Harbour (GHB)
8.6/10 Excellent! (105 reviews)
I highly recommend staying at Sky Beach Club to anyone visiting Eleuthera in the future. The room was clean, communication was always clear, and the staff was friendly and responsive. All around a great place to stay!

Reviewed on May 9, 2026

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

4 out of 5
Save 100% on your flight
Price was $3,935, price is now $2,074 per person
$2,074
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Nassau (NAS)
8/10 Very Good! (3,852 reviews)
All of the staff were exceptional! Beautiful spirited people. I Love me some Bahamians.

Reviewed on May 28, 2026

Viva Fortuna Beach by Wyndham, A Trademark All Inclusive

Viva Fortuna Beach by Wyndham, A Trademark All Inclusive

3.5 out of 5
Save 100% on your flight
Price was $1,546, price is now $907 per person
$907
per person
Aug 15 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Freeport (FPO)
6.8/10 (1,010 reviews)
The food was excellent, the water temperature and sand are great. The service was good. However They should clean the seaweeds on the shore and do something about the rocks upon entering the water not to injure people.

Reviewed on May 22, 2026

Saint Francis Resort

Saint Francis Resort

3.5 out of 5
Save 100% on your flight
Price was $2,104, price is now $1,354 per person
$1,354
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to George Town (GGT)
9.2/10 Wonderful! (162 reviews)
We enjoyed our getaway. Beautiful views of bay and ocean. Our room overlooked the turquoise ocean water. What a spectacular way to wake up and fall asleep with sound and sight of waves. Staff was very kind. Family style place-don’t expect luxury here. Rooms are clean and has coffee machine with pods and mini fridge. Wonderful time to chill and let go as it’s a simple island lifestyle. Enjoyed use of kayaks exploring waters and surroundings. .

Reviewed on May 4, 2026

Pink Sands Resort

Pink Sands Resort

4 out of 5
Save 100% on your flight
Price was $6,904, price is now $4,807 per person
$4,807
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to North Eleuthera (ELH)
8.6/10 Excellent! (122 reviews)
Friendly customer service, beautiful room and great food!

Reviewed on Jan 20, 2026

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Chesters Hotel Deals

Chesters Bonefish Lodge

Chesters Bonefish Lodge

3 out of 5
Chester's Bay Chesters Acklins Island
$230 nightly
The price is $253 total per night from May 29 to May 30
$253 total
May 29 - May 30
Total with taxes and fees
Chesters Bonefish Lodge
Chester's Highway Inn Bone Fish Lodge

Chester's Highway Inn Bone Fish Lodge

4 out of 5
Chester's Bay Chesters Acklins Island
Get rates
Chester's Highway Inn Bone Fish Lodge
Nature's Delight Lodge

Nature's Delight Lodge

3 out of 5
Queen's Highway Colonel Hill Crooked Island
Get rates
Nature's Delight Lodge
See all 4 properties in Chesters
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 Chesters Vacation Packages

Chesters Essential Information

Language
English
Currency
Bahamian dollars
Closest Airport
Colonel Hill Airport (CRI)
Max Temp Winter
75ºF
Max Temp Summer
80ºF

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Frequently asked questions

How much does a Chesters vacation package cost?
You can pick up a vacation package to this top destination from $748 on Expedia. But how much your vacation to Chesters costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Chesters?
If you're looking to snag a cheap Chesters vacation package, consider traveling in June, September and December. You're likely to find lower prices on flights and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Chesters?
Typically, a handful of days is enough to visit the major sights during your Chesters vacation. However, if you prefer to have more time to unwind or take day trips, think about extending your itinerary.
How to find the best Chesters package deals?
Use Expedia's filter tool to find some great Chesters package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Chesters package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chesters vacation as a package?
You can enjoy significant savings on your Chesters break by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to browse the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chesters?
If you're planning a spontaneous Chesters adventure, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Chesters vacation packages?
Your Chesters trip is meant to be a relaxing escape from your busy life, not a source of money-related stress. So to allow you that extra flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.