Chesters Vacations from $719

Book a Hotel + Flight or Car together to unlock savings

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.
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 $1,315, price is now $719 per person
$719
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Freeport (FPO)
6.8/10 (1,005 reviews)
Entertainment was really good,very talented people,and the staff was very nice...beach was beautiful, but the Food was lacking everything seemed very generic...We didnt get to experience the reservation restaurants so I cannot review those,but the buffet was left to be desired...

Reviewed on Sep 8, 2025

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

4 out of 5
Price was $2,249, price is now $1,138 per person
$1,138
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nassau (NAS)
8/10 Very Good! (3,250 reviews)
The bar was good and very well attended Air conditioned was good and cold

Reviewed on Oct 9, 2025

Rosewood Baha Mar

Rosewood Baha Mar

5 out of 5
Save 100% on your flight
Price was $2,690, price is now $1,662 per person
$1,662
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nassau (NAS)
9/10 Wonderful! (329 reviews)
The pool, hot tub, resort restaurants and the beach was wonderful, the service excellent. The casino it is just for entertainment purposes on my respective opinion, you never win .

Reviewed on Sep 22, 2025

Goldwynn Resort & Residences

Goldwynn Resort & Residences

5 out of 5
The Grove
Save 100% on your flight
Price was $1,678, price is now $1,114 per person
$1,114
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nassau (NAS)
9.2/10 Wonderful! (409 reviews)
My partner and I had a wonderful stay here! The hotel was spotless from top to bottom — everything felt so clean and well taken care of. The food was absolutely amazing (we honestly looked forward to every meal), and the beach and pool areas were just perfect — crystal-clear water, soft sand, and breathtaking views of the turquoise Bahamian ocean. The atmosphere was peaceful yet vibrant, and the staff were kind and attentive throughout our stay. Specially Maria at the restaurant OIA!!! We will definitely plan another stay. It was the perfect mix of relaxation and indulgence. We can’t wait to come back!

Reviewed on Oct 4, 2025

The Cove at Atlantis

The Cove at Atlantis

5 out of 5
Save 100% on your flight
Price was $3,485, price is now $2,356 per person
$2,356
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nassau (NAS)
8.6/10 Excellent! (1,004 reviews)
Everything was amazing

Reviewed on Oct 9, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chesters
View all trips

Chesters Hotel Deals

Chesters Bonefish Lodge

Chesters Bonefish Lodge

3 out of 5
Chester's Bay, Chesters, Acklins Island
Get rates
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
4 bedroom 4 bath home in crooked island bahamas perfect for Bone fishing.

4 bedroom 4 bath home in crooked island bahamas perfect for Bone fishing.

Colonel Hill
Get rates
4 bedroom 4 bath home in crooked island bahamas perfect for Bone fishing.
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.

Chesters Essential Information

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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chesters vacation package cost?
You can pick up a vacation package to this top destination from $719 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.