Chesters Vacations from $1,260

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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.
Sir Charles Guest House

Sir Charles Guest House

3 out of 5
Price was $3,533, price is now $1,260 per person
$1,260
per person
Feb 15 - Feb 20
found 2 hours ago
Roundtrip non-stop flight included
New York (JFK) to North Eleuthera (ELH)
9.8/10 Exceptional! (19 reviews)
Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

4 out of 5
Price was $4,543, price is now $2,093 per person
$2,093
per person
Mar 3 - Mar 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nassau (NAS)
8/10 Very Good! (3,391 reviews)
Restaurant food was just middleing. Nothing special. Everything by app

Reviewed on Jan 10, 2026

Winfield Manor 3 Bedroom Home

Winfield Manor 3 Bedroom Home

3 out of 5
Price was $4,709, price is now $2,397 per person
$2,397
per person
Feb 15 - Feb 20
found 2 hours ago
Roundtrip non-stop flight included
New York (JFK) to Governor's Harbour (GHB)
No reviews
Grand Hyatt Baha Mar

Grand Hyatt Baha Mar

4.5 out of 5
Save 100% on your flight
Price was $2,900, price is now $1,711 per person
$1,711
per person
Mar 3 - Mar 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nassau (NAS)
8.6/10 Excellent! (4,596 reviews)
The room services was spotless, the 99%of the staff was courteous, the amenities were unbelievable!!!

Reviewed on Jan 9, 2026

Aqua Vista 2 Bedroom Home

Aqua Vista 2 Bedroom Home

3 out of 5
Price was $6,010, price is now $3,605 per person
$3,605
per person
Feb 15 - Feb 20
found 2 hours ago
Roundtrip non-stop flight included
New York (JFK) to Governor's Harbour (GHB)
No reviews
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Chesters Hotel Deals

Chesters Bonefish Lodge

Chesters Bonefish Lodge

3 out of 5
Chester's Bay Chesters Acklins Island
$286 nightly
The price is $315 total per night from Jan 11 to Jan 12
$315 total
Jan 11 - Jan 12
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 $1,260 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.