Chesters Vacations from $971

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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.
Grand Hyatt Baha Mar

Grand Hyatt Baha Mar

4.5 out of 5
Save 100% on your flight
Price was $1,434, price is now $971 per person
$971
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nassau (NAS)
8.6/10 Excellent! (4,387 reviews)
The biggest set back was the staff, they can learn to be friendlier. For the amount of money spent they should step up the hospitality.

Reviewed on Aug 25, 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 $3,143, price is now $1,527 per person
$1,527
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nassau (NAS)
8/10 Very Good! (3,177 reviews)
The staff was amazing! They were friendly, accommodating, and helpful. Couldn’t ask for better service.

Reviewed on Aug 24, 2025

Grand Isle Resort & Residences

Grand Isle Resort & Residences

4 out of 5
Save 100% on your flight
Price was $3,479, price is now $2,123 per person
$2,123
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GGT)
9.2/10 Wonderful! (394 reviews)
This is the secret jewel of our trip. I’ll never go back to Atlantis, but I will definitely be back to the Exumas. Grand Isle staff are friendly and attentive. We stayed in a 3 bedroom villa and it was perfect. IT perfectly compliments the beauty of the Great Exuma island.

Reviewed on Aug 16, 2025

Abaco Beach Resort and Boat Harbour Marina

Abaco Beach Resort and Boat Harbour Marina

3.5 out of 5
Save 100% on your flight
Price was $2,395, price is now $1,588 per person
$1,588
per person
Nov 1 - Nov 8
found 5 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Marsh Harbour (MHH)
8.2/10 Very Good! (302 reviews)
I did not like the bed, too many screeching sounds .

Reviewed on Aug 24, 2025

Goldwynn Resort & Residences

Goldwynn Resort & Residences

5 out of 5
The Grove
Save 100% on your flight
Price was $1,915, price is now $1,358 per person
$1,358
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nassau (NAS)
9.4/10 Exceptional! (396 reviews)
Great place, good food and superb attention. 100% recommended. Beach needs a cleanup, too much seaweed on the sand when you get in the water feels sketchy on the feet.

Reviewed on Aug 24, 2025

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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 Aug 26 to Aug 27
$315 total
Aug 26 - Aug 27
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
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.

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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 $971 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.