Holiday Rentals in Chelston

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Holiday Rentals in Chelston

Holiday Home in Paget

10.0 out of 10, Exceptional, (4)
"Fantastic property- conveniently located and as advertised! "
Canada
Adam M.
Entire Private Vacation Villa 3 Bedrooms Pool nr Beach in Bermuda.

Aparthotel in Pembroke Parish

3.5 star property
8.6 out of 10, Excellent, (182)
"Great little quaint local property, clean, a quiet and walkable to Front street shops and restaurants. "
United States
Jennifer
The price is €325
includes taxes & fees
30 Nov - 1 Dec
Rosemont Guest Suites

Apartment in Warwick Parish

3.0 star property
9.4 out of 10, Exceptional, (53)
"Excellent stay Will return "
United States
Sherri
Seven Arches

Holiday Home in Devonshire

9.8 out of 10, Exceptional, (128)
"Loved this rental! The owner is so nice, the location is beautiful, and the house is so spacious. Very chill environment, probably not great for anyone who want to be in the center of the action. My group had an amazing time, the ocean access got a little hairy because of the impending hurricane, but when the water was calm, it was perfection. Would definitely stay here again!"
United States
Constance f.
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!

Aparthotel in Pembroke Parish

3.0 star property
8.8 out of 10, Excellent, (93)
"Place was really clean and big, Roslyn was very caring and helpful. Great place to stay!!!!"
United States
Henry
Windsong Guest Apartments

Cottage in Somerset Village

9.8 out of 10, Exceptional, (167)
"As always, Perfect location. Perfect host. Perfect water. "
United States
LU S.
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....

Cottage in Smiths

10.0 out of 10, Exceptional, (125)
"The hosts, Chris and Gail are wonderful. Tilly, their dog, is adorable. The pool house was perfect for us. We went to Bermuda for a wedding, and stayed for a week. We had plenty of room. You can’t beat the location. We highly recommend this property to anyone!"
United States
Dawn
Pool House Studio In A Garden Setting + EV chargers

Villa in Somerset village

10.0 out of 10, Exceptional, (41)
"Nice, spread out house that provides indoor and outdoor space to congregate but also privacy in bedrooms and bathrooms. 2 minute walk to beach with chairs and umbrellas and 5 minute walk to Somerset long bay beach. Walkable to good size grocery store, a few takeout restaurants and bus stop. The nooks and crannies of the property are amazing. Hammock, moon gate, benches, outdoor showers, so many birds and gorgeous lush foliage surround the house. "
United States
Heather D.
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!

Apartment in Devonshire

10.0 out of 10, Exceptional, (3)
"It is an amazing place**so many amenities.Joe and Florence are Very nice and Helpful!!!Highly recommended them and the apartment ; } "
Canada
Garth W H G.
Charming 1-bedroom apartment centrally located to all that Bermuda has to offer

Holiday Home in Smith's Parish

9.2 out of 10, Wonderful, (40)
"Property location is a 10! This house is directly across from John Smith's Bay, one of the best beaches in Bermuda. Beach chairs and umbrellas are provided in addition to all necessary kitchen/bath amenities. Bus stops are conveniently located close by. Well stocked grocery store is a quick bus ride away. Property could use some updating, but did not deter our wonderful vacation."
United States
Betty R.
Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style

Apartment in Southampton

9.8 out of 10, Exceptional, (136)
"Perfect location - lovely stay - great hostess - thank you Lorna x"
United Kingdom
Susan H.
Spacious Beachfront and Private Resort living

Holiday Home in Southampton

10.0 out of 10, Exceptional, (123)
"Amazing property and amazing host "
United States
Robert C.
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course

Apartment in Pembroke

10.0 out of 10, Exceptional, (2)
"Clean, comfortable and exactly as advertised. Close to all amenities and a great location for all of the activities we had planned - good Bermuda value!"
Canada
Thomas W.
Tranquil, Roomy Getaway - Close to City of Hamilton

Apartment in Paget Parish

10.0 out of 10, Exceptional, (2)
"Location "
United Kingdom
clare a.
Tiny Studio in fabulous Smith's Parish at John Smith's Bay Beach

Apartment in 5 Cross Bay Road

10.0 out of 10, Exceptional, (150)
"Wendell was an absolutely awesome host! Very friendly and willing to help whenever possible! You can’t beat a better location, just a short walk to the beach and the view is absolutely spectacular! We truly enjoyed our stay in Bermuda! Thank you, Wendell! "
United States
Jim M.
LOCATION! LOCATION! - Whispering Waves Apt, at Cross Bay Private Estate & Beach

Cottage in Southampton Parish

9.2 out of 10, Wonderful, (7)
"A small, clean, well-equipped apartment that is a great jumping off point for exploring the wonders of Bermuda."
United States
Claire A.
Coral Suite - close to beaches/kayaks/dock/stunning views/EVcharger

Holiday Home in Southampton

10.0 out of 10, Exceptional, (74)
"We were all amazed at the beach view from the house. It was so perfect and we would all stay again there. Jessica was a great hostess who answered every and all our questions and requests. I give this hour a 10 out of 10Stay here, you won’t regret it. "
United States
jackie k.
Stunning Views of Horseshoe Bay Beach. Enjoy the sounds of the lapping waves!

Apartment in Sandy's

9.8 out of 10, Exceptional, (98)
"A well provisioned and conveniently located accommodation, with a charming and hospitable host."
Canada
Alix W.
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!

Cottage in Warwick

9.8 out of 10, Exceptional, (102)
"Perfect location, clean and Nice accommodation "
France
Olivier M.
Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.

Apartment in Sandys

10.0 out of 10, Exceptional, (93)
"Great sunset from the lawn, great snorkeling, and a comfortable bed. "
United States
James W.
Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment
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.
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Top Chelston Hotel Reviews

Find out more about Chelston

Everything you need to know about Chelston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chelston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chelston holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chelston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chelston. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chelston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chelston holiday rentals we have selected for you start as low as €325 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chelston rentals

At Expedia, we put the best Chelston holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chelston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chelston holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chelston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Chelston?

Yes, there are holiday rentals close to the most popular sights in Chelston, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chelston has to offer?

Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach: This highly rated holiday home rental in Chelston is located next to a golf course, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

What’s there to see and do in Chelston?

Explore the area and family-friendly sights such as Bermuda Aquarium Museum and Zoo (BAMZ), or get out into nature at a spot like Elbow Beach. Front Street and Fort Hamilton are a couple of places you'll find in the wider area.

What’s a holiday rental in Chelston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chelston. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for small groups.