Chelston Holiday Rentals

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Holiday Rentals in Chelston

Rosemont Guest Suites
3.5 star property
8.6 out of 10, Excellent, (181)
"Great little quaint local property, clean, a quiet and walkable to Front street shops and restaurants. "
United States
Jennifer
The price is NZ$656
includes taxes & fees
26 Oct - 27 Oct
Rosemont Guest Suites
Seven Arches
3.0 star property
9.4 out of 10, Exceptional, (51)
"We had a fantastic time. The beds were supper comfy, the house was clean, beautiful decorated, landscaping was gorgeous, and the neighbors were all friendly and quiet. Will stay again."
United States
Angela
Seven Arches
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
9.8 out of 10, Exceptional, (165)
"Once again, we really enjoyed our stay. This has to be the best little cottage in Bermuda. Thank you and see you soon. Jo and Ed"
United States
JOANN L.
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!
9.8 out of 10, Exceptional, (127)
"the views are breath taking house needs some work but being on the water will beat any property up"
United States
bill f.
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!
Spacious Beachfront and Private Resort living
9.8 out of 10, Exceptional, (135)
"This is a lovely property that has all basic features and amenities for a casual comfortable stay. The location is out of this world-overlooking the ocean with just steps down to a secluded beach that feels almost like a private beach. The hosts are very welcoming and accommodating. We look forward to booking with them again. It was an absolutely incredible summer vacation. "
United States
Elena T.
Spacious Beachfront and Private Resort living
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!
10.0 out of 10, Exceptional, (117)
"The apartment was very good, clean and handy to bus stops"
Canada
Helen Yee Wun
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!
Coral Suite - close to beaches/kayaks/dock/stunning views/EVcharger
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
Windsong Guest Apartments
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
Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach
10.0 out of 10, Exceptional, (3)
"Fantastic property- conveniently located and as advertised! "
Canada
Adam M.
The price is NZ$1,252
includes taxes & fees
12 Nov - 13 Nov
Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach
Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun
9.4 out of 10, Exceptional, (30)
"Loved the uniqueness of the cottage. Comfortable and cozy. "
United States
Dorothy L.
Magical private estate:3 bed Sage Cottage,big porch near Cambridge Beaches & fun
Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........
10.0 out of 10, Exceptional, (14)
"I travel to Bermuda on business several times a year and have stayed at a host of different places from resorts/hotels to rentals and this one is hands down the best so far.Spacious and clean with all of the necessary amenities to make my stay comfortable and enjoyable.The water pressure was the best I've experience on island and having a grocery store less than a 1/2 mile away was super convenient (although it is closed on Sundays).Austin was a great host and I plan on staying with him again!"
United States
Bill M.
Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........
Location! Location! HALF PRICE SALE @ 100 Daily, November 9th - December 9th ASK
10.0 out of 10, Exceptional, (148)
"⭐️💌TOP HOST & LOCATION⭐️💌Perfect 4 Couples Looking for Serenity & a Secure Sanctuary💌⭐️40+YEAR HOST Hospitality & Guidance if Needed💌⭐️PRIVATE ACCESS TO THE BEST SOUTH SHORE~CROSS BAY BEACH⭐️💌Full Amenities on Property w/Transportation Available⭐️💌KINDNESS MATTERS as this is what Host Wendell & his family are all about💓Lynn&Mark, June 2025"
United States
Lynn
Location! Location! HALF PRICE SALE @ 100 Daily, November 9th - December 9th ASK
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!
10.0 out of 10, Exceptional, (41)
"Overall a very nice property. We like to be off the beaten track and it certainly was."
United States
Underpressure S.
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!
Waterfront 2 Bedroom Cottage, Access to Private Beach
9.6 out of 10, Exceptional, (56)
"We had a wonderful time, super clean and absolutely lovely accommodation. There’s a nice swimming area out the back. Perfectly located right beside the ferry terminal!"
Canada
Kaan C.
Waterfront 2 Bedroom Cottage, Access to Private Beach
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!
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!
Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment
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
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course
10.0 out of 10, Exceptional, (122)
"Loved the property, the incredible views and the responsiveness of host. Great location on the island. "
United States
Martha L.
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course
Smugglers Cove - Walk to City of Hamilton
10.0 out of 10, Exceptional, (49)
"This is a beautiful cottage, tropical surroundings, pool, and very attentive hosts with tons of local knowledge, that they are more than happy to share. Perfectly located for, dining, shopping, excursions and more. Book it, you be glad you did."
United States
Tom
Smugglers Cove - Walk to City of Hamilton
Wyndham Water Views
9.2 out of 10, Wonderful, (11)
"This was a great property. We really enjoyed our stay. The access to the railway walking path was really nice and the views were spectacular. "
United States
Mark Wheeler
Wyndham Water Views
Lovely private studio apartment in beautiful garden setting
9.8 out of 10, Exceptional, (25)
"Property was extremely clean, well taken care of and made our stay in Bermuda that much more enjoyable! Cannot thank the hosts enough for their hospitality. "
United States
Henry S.
Lovely private studio apartment in beautiful garden setting
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, 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 NZ$656 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?

Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!: This holiday home rental outside of Chelston is located by the ocean, and has a patio, a selection of games and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Hamilton Ferry Dock 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.