Chelston Holidays

    deals illustration
    Better together
    Save up to S$134 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Chelston

Hamilton Princess & Beach Club - a Fairmont Managed Hotel
Hamilton Princess & Beach Club - a Fairmont Managed Hotel
4.5 out of 5
76 Pitts Bay Road, Pembroke Parish
Fully refundableReserve now, pay when you stay
The price is S$1,068 per night from 20 Jul to 21 Jul
S$1,068
20 Jul - 21 Jul
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Very friendly staff."

Reviewed on 17 Jun, 2025

Hamilton Princess & Beach Club - a Fairmont Managed Hotel
Grotto Bay Beach Resort
Grotto Bay Beach Resort
4 out of 5
11 Blue Hole Hill, Bailey's Bay, Hamilton Parish
The price is S$921 per night from 8 Jul to 9 Jul
S$921
8 Jul - 9 Jul
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Very convenient to the airport. The pool and beach are good but can get crowded. Many people elect the all inclusive option so you do get families with children. I did not elect all inclusive but we could eat at the restaurants in a pay as you go. Dive and snorkel trips to the reef(s) available on ..."

Reviewed on 20 Jun, 2025

Grotto Bay Beach Resort
The St. Regis Bermuda Resort
The St. Regis Bermuda Resort
5 out of 5
34 Coot Pond Road, Town of St. George
The price is S$1,585 per night from 23 Jun to 24 Jun
S$1,585
23 Jun - 24 Jun
includes taxes & fees
8.8/10 Excellent! (199 reviews)
"Very beautiful property and stay, perfect place for relaxing. Can be a little expensive, but it was definitely worth it."

Reviewed on 10 Jun, 2025

The St. Regis Bermuda Resort
See all 269 properties in Chelston
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.

Frequently asked questions

How much does a Chelston holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Chelston costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chelston?
If you're hoping to score a cheap Chelston holiday package, consider travelling in January, February and March. You'll typically find better prices on hotels and flights during these months --- perfect for a budget-friendly getaway.
How many days is enough for Chelston?
Generally, a handful of days is enough to visit the top sights during your Chelston holiday. However, if you prefer to have some time to kick back or take day trips, consider extending your trip.
How to find the best Chelston package deals?
Use Expedia's filter tool to find some great Chelston package deals. When you begin your search, simply 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 Chelston package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book a Chelston holiday as a package?
You can enjoy significant savings on your next Chelston getaway by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Chelston?
Enjoy incredible discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Chelston adventure.
How to plan a trip to Chelston?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favourite season and the activities available will also help you decide when to escape to Chelston.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to experiences and flights. Your accommodation will likely be the biggest expense during your trip to Chelston.
  3. Decide how long to go for: Now that you know more about Chelston, you can work out the perfect length of your holiday. Pull together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Combine your airfare and accommodation: After you've nailed down your trip dates and duration, lock in the right Chelston holiday package for you.

Popular places to visit

Bermuda Botanical Gardens

3.5/5(6 reviews)

Explore the lovely green spaces of Bermuda Botanical Gardens and enjoy the golf courses in Paget Parish. Wander the beautiful beaches and seaside in the area.

Bermuda Botanical Gardens

What to do in Chelston

Bermuda Beach Bonfire with Dark and Stormy Cocktail Included

Bermuda Beach Bonfire with Dark and Stormy Cocktail Included

S$276
per adult
Bermuda Beach Bonfire with Dark and Stormy Cocktail Included
Bermuda Railway Trail and Off The Beaten Path Walking Experience

Bermuda Railway Trail and Off The Beaten Path Walking Experience

S$161
per adult
Bermuda Railway Trail and Off The Beaten Path Walking Experience
Kona, Sailing along the North Shore of Bermuda

Bermuda Private Catamaran:Snorkeling, Shipwrecks & Cliff Jumping

S$1,412
per traveller
Bermuda Private Catamaran:Snorkeling, Shipwrecks & Cliff Jumping
See all activities in Chelston

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.