Chelston Vacations from $1,313

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Your Chelston Vacation

When you choose a Chelston vacation package, it's all about enjoying your escape to the fullest. Delve into the best parts of this lively city knowing that everything has been organized in advance. If your trip to Chelston includes a little sightseeing, drop by famous attractions like Elbow Beach, Bermuda Botanical Gardens and Camden House. Don't put off visiting this city any longer. Your perfect Chelston vacation is just a few clicks away with Expedia.

The Latest Chelston vacation packages

Price found within the past 48 hours. Click for updated prices.
The Reefs Resort & Club

The Reefs Resort & Club

4 out of 5
Price was $1,837, price is now $1,313 per person
$1,313
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
9.6/10 Exceptional! (1,009 reviews)
Perfect in every way!

Reviewed on Oct 25, 2025

Hamilton Princess - Fairmont Gold Experience

Hamilton Princess - Fairmont Gold Experience

5 out of 5
Save 100% on your flight
Price was $2,565, price is now $1,776 per person
$1,776
per person
Jan 19 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. George's (BDA)
9.2/10 Wonderful! (39 reviews)
Beautiful property. Delicious breakfast on the Gold floor. Amazing staff!

Reviewed on Oct 12, 2025

Azura Bermuda

Azura Bermuda

4 out of 5
Price was $2,057, price is now $1,510 per person
$1,510
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
9.2/10 Wonderful! (287 reviews)
We had a security issue with our room and asked to be moved but the staff was unable to accommodate us.

Reviewed on Oct 25, 2025

Rosedon Hotel

Rosedon Hotel

4 out of 5
Price was $2,022, price is now $1,521 per person
$1,521
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
9.8/10 Exceptional! (335 reviews)
Amazing stay and great customer service. Would absolutely return for another stay!

Reviewed on Sep 6, 2025

St George's Club Hotel

St George's Club Hotel

2 out of 5
Price was $1,738, price is now $1,353 per person
$1,353
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
9.2/10 Wonderful! (162 reviews)
Absolutely love the units. Much better than just a hotel room!

Reviewed on Oct 17, 2025

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Discover the most popular places to visit in Chelston

Bermuda Botanical Gardens

4/5(88 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

Masterworks Museum of Bermuda Art

You can spend time studying the exhibits at Masterworks Museum of Bermuda Art in Paget Parish. Wander the beautiful beaches and seaside in the area.

Masterworks Museum of Bermuda Art

Camden House

4.5/5(2 reviews)

Find out about the history of Paget Parish when you spend time at Camden House. Amble around the area's beautiful beaches or seek out the golf courses.

Camden House

What to do in Chelston

Hamilton Shopping & Sightseeing

Hamilton Shopping & Sightseeing

$100
per adult
Hamilton Shopping & Sightseeing
Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

$138
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
Crystal Caves, Hamilton Shopping and Beach Tour

Crystal Caves, Hamilton Shopping and Beach Tour

$150
per adult
94% of travellers recommend
Crystal Caves, Hamilton Shopping and Beach Tour
See all activities in Chelston

Chelston Hotel Deals

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
$465 nightly
The price is $519 total per night from Nov 21 to Nov 22
$519 total
Nov 21 - Nov 22
Total with taxes and fees
9.2/10 Wonderful! (1,012 reviews)
Best hotel

Reviewed on Oct 14, 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
$389 nightly
The price is $436 total per night from Nov 25 to Nov 26
$436 total
Nov 25 - Nov 26
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
Beautiful resort and close to airport

Reviewed on Oct 23, 2025

Grotto Bay Beach Resort
The Reefs Resort & Club

The Reefs Resort & Club

4 out of 5
56 South Shore Road, Southampton Parish
$404 nightly
The price is $454 total per night from Oct 28 to Oct 29
$454 total
Oct 28 - Oct 29
Total with taxes and fees
9.4/10 Exceptional! (1,013 reviews)
The reefs is a gorgeous and professionally run property that we would highly recommend. We would have rated the staff and service a 5 except for the bar which is staffed by bartenders that are not at all friendly or accommodating. The exception was Jennifer who was a delight! The staff in all other ...

Reviewed on Oct 25, 2025

The Reefs Resort & Club
See all 285 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.

Find the Best Chelston Vacation Packages

Chelston Essential Information

Language
English
Currency
Bermudian dollars
Closest Airport
L.F. Wade Intl. Airport (BDA)
Max Temp Winter
70ºF
Max Temp Summer
80ºF
Top Sights
Masterworks Museum of Bermuda Art, Bermuda Botanical Gardens and Camden House

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Frequently asked questions

How much does a Chelston vacation package cost?
Offering excellent value package deals from $1,313 on Expedia, you'll be pleasantly surprised at how much a vacation 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 looking to book a cheap Chelston vacation package, consider visiting in June, October and December. You'll typically find lower rates on flights and hotels during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Chelston?
The ideal duration of your Chelston vacation depends on what you'd like to see and do. Generally, a handful of days to a week will give you enough time to go to all the main attractions and discover some hidden treasures along the way.
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 vacation package well in advance.
Is it cheaper to book a Chelston vacation as a package?
You can enjoy significant savings on your next Chelston getaway by booking a personalized vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Chelston vacation packages?
If you're anything like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Chelston vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.