Chesters Vacations from $1,115

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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.
British Colonial - Nassau

British Colonial - Nassau

4 out of 5
Downtown Nassau
Save 100% on your flight
Price was $1,792, price is now $1,115 per person
$1,115
per person
Mar 30 - Apr 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nassau (NAS)
8.6/10 Excellent! (2,034 reviews)
Friendly staff, small shower, more food options at resort would be ideal.

Reviewed on Feb 23, 2026

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

4 out of 5
Price was $3,629, price is now $1,740 per person
$1,740
per person
Apr 28 - May 3
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Nassau (NAS)
8/10 Very Good! (3,391 reviews)
The room was OK I don’t feel as though the air conditioning was working thoroughly. I also feel that the bed was not that comfy.

Reviewed on Feb 25, 2026

Grand Hyatt Baha Mar

Grand Hyatt Baha Mar

4.5 out of 5
Save 100% on your flight
Price was $2,750, price is now $1,650 per person
$1,650
per person
Apr 11 - Apr 18
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Nassau (NAS)
8.6/10 Excellent! (4,596 reviews)
One of the best resorts I have ever stayed at!!

Reviewed on Feb 25, 2026

Viva Fortuna Beach by Wyndham, A Trademark All Inclusive

Viva Fortuna Beach by Wyndham, A Trademark All Inclusive

3.5 out of 5
Price was $1,797, price is now $1,200 per person
$1,200
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Freeport (FPO)
6.8/10 (1,001 reviews)
Rooms were clean could use some updating but otherwise perfect for what we needed. Staff very nice and accomodating. Outdoor space awesome!

Reviewed on Feb 17, 2026

Goldwynn Resort & Residences

Goldwynn Resort & Residences

5 out of 5
The Grove
Save 100% on your flight
Price was $2,113, price is now $1,442 per person
$1,442
per person
Apr 28 - May 3
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Nassau (NAS)
9.2/10 Wonderful! (427 reviews)
Hotel is only 3 years old. Everyone was pleasant. Real close to other restaurants. But the restaurant on property was fantastic

Reviewed on Feb 23, 2026

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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 Feb 26 to Feb 27
$315 total
Feb 26 - Feb 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
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 $1,115 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.