Chelston Holidays

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Top hotels in Chelston

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$1,124 per night from 2 Sept to 3 Sept
S$1,124
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (228 reviews)
"Nice hotel clean and very attentive staff nice beach and pool areas"

Reviewed on 14 Aug, 2025

The St. Regis Bermuda Resort
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$712 per night from 9 Sept to 10 Sept
S$712
9 Sept - 10 Sept
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"This is my second time at this resort and I noted that they have made major additions during COVID. The location of this resort is excellent for an active traveller as you can easily jump on the bus in both directions. We even took the bus from the airport but it is only possible with small carry-ons. ..."

Reviewed on 19 Aug, 2025

Grotto Bay Beach Resort
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$743 per night from 24 Aug to 25 Aug
S$743
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Can’t go wrong with the Princess!"

Reviewed on 17 Aug, 2025

Hamilton Princess & Beach Club - a Fairmont Managed Hotel
See all 273 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.

Popular places to visit

Bermuda Botanical Gardens

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
Make the Most of Your Time Together!

East End Excursion: Private Guided Family Tour in Bermuda

S$122
per adult
East End Excursion: Private Guided Family Tour in Bermuda
Kona, Sailing along the North Shore of Bermuda

Bermuda Private Catamaran:Snorkeling, Shipwrecks & Cliff Jumping

S$1,407
per traveller
Bermuda Private Catamaran:Snorkeling, Shipwrecks & Cliff Jumping
See all activities in Chelston

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.

* 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.