Chelston Holidays

  • Plan, book, travel with confidence

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

Top hotels in Chelston

Cambridge Beaches Resort & Spa
Cambridge Beaches Resort & Spa
4 out of 5
30 Kings Point Road Somerset, Mangrove Bay, Sandys Parish
The price is S$662 per night from 2 Apr to 3 Apr
S$662
includes taxes & fees
2 Apr - 3 Apr
9.2/10 Wonderful! (960 reviews)
"We went for our honeymoon and it was perfect, quiet but fun,beautiful beaches and our room was amazing."

Reviewed on 13 Mar,2025

Cambridge Beaches Resort & Spa
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$527 per night from 1 Apr to 2 Apr
S$527
includes taxes & fees
1 Apr - 2 Apr
9/10 Wonderful! (1,001 reviews)
"I have stayed at Grotto Bay 3 times and it just get better and better. The addition to the dining and rooftop areas turned out beautiful. The property is gorgeous and so well maintained. The restaurant breakfast is amazing and we ate lunch and dinner there as well. All very good food. I will be returning ..."

Reviewed on 19 Mar,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
The price is S$675 per night from 6 Apr to 7 Apr
S$675
includes taxes & fees
6 Apr - 7 Apr
9/10 Wonderful! (1,000 reviews)
"Spectacular! Before we arrived in Bermuda, the concierge team was reaching out to ensure everything we needed was in place. We were greeted at the doors with such warmth and then swisked off to the Fairmont lounge for a private check-in. The suite was awesome (large, breathtaking view, huge bathroom, ..."

Reviewed on 13 Mar,2025

Hamilton Princess & Beach Club - a Fairmont Managed Hotel
See all 259 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$290
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$168
per adult
Bermuda Railway Trail and Off The Beaten Path Walking Experience
Bermuda Rum Swizzle Sip & Sample Tour

Bermuda Rum Swizzle Sip & Sample Tour

S$350
per adult
Bermuda Rum Swizzle Sip & Sample Tour
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.