Chelston Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Chelston

Coco Reef Bermuda

Coco Reef Bermuda

3.5 out of 5
3 Stonington Circle Paget Parish
The price is S$637 per night from 20 Jul to 21 Jul
S$637
20 Jul - 21 Jul
includes taxes & fees
8.4/10 Very good! (1,006 reviews)
"The property itself was very nice and we had a beautiful view of the beach. The room was clean for the most part. The location of the hotel was great. It was right between Hamilton and the beaches on the South Shore as well as on a central bus route. The only things that I had issues with was that ..."

Reviewed on 8 Jul, 2026

Coco Reef Bermuda
Dawkins Manor Hotel

Dawkins Manor Hotel

3 out of 5
29 St. Michaels's Road Paget Parish
8.4/10 Very good! (160 reviews)
"I had a great stay at Dawkins Manor Hotel while I was in Bermuda. The property was very clean and comfortable, and Celia was absolutely lovely to deal with. The rooms are a bit dated, but had all the amenities I needed throughout my stay. The area where the hotel is located was safe and quiet, and ..."

Reviewed on 6 Jul, 2026

Get rates
Dawkins Manor Hotel
Hamilton Princess & Beach Club - A Fairmont Hotel

Hamilton Princess & Beach Club - A Fairmont Hotel

4.5 out of 5
76 Pitts Bay Road Pembroke Parish
Fully refundableReserve now, pay when you stay
The price is S$1,209 per night from 2 Aug to 3 Aug
S$1,209
2 Aug - 3 Aug
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"The staff at The Hamilton is top notch but the room this time was a real disappointment. This is our third time visiting within 12 months. We have always booked the Fairmont Gold Room. Previously we have had wonderful balcony rooms with beautiful views. This time we were given a room overlooking ..."

Reviewed on 7 Jul, 2026

Hamilton Princess & Beach Club - A Fairmont Hotel
See all 266 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.

What to do in Chelston

A Bermuda Exquisite Experience with FREE Scenic Ferry Return

A Bermuda Exquisite Experience with FREE Scenic Ferry Return

S$97
per adult
A Bermuda Exquisite Experience with FREE Scenic Ferry Return
Restless Native Catamaran Sail and Snorkel Tour

Restless Native Catamaran Sail and Snorkel Tour

S$123
per adult
92% of travellers recommend
Restless Native Catamaran Sail and Snorkel Tour
Crystal Cave, St. George and Tobacco Bay Beach

Crystal Cave, St. George and Tobacco Bay Beach

S$194
per adult
Crystal Cave, St. George and Tobacco Bay Beach
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.

Explore a world of travel with Expedia

* 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.