Chelston Holiday Rentals

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Holiday Rentals in Chelston

Our top choices for Chelston holiday rentals

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. "
The price is NZ$635
includes taxes & fees
12 Sept - 13 Sept
Rosemont Guest Suites

Seven Arches

3.0 star property
9.4 out of 10, Exceptional, (48)
"Nice property "
Seven Arches

Your Private Luxury Villa - 3 Bedrooms, House & Cottage, Pool, Walk to Beach!

10.0 out of 10, Exceptional, (1)
"Fantastic property- conveniently located and as advertised! "
Your Private Luxury Villa - 3 Bedrooms, House & Cottage, Pool, Walk to Beach!

Windsong Guest Apartments

3.0 star property
8.8 out of 10, Excellent, (93)
"Very clean and beautifully built and maintained property with friendly hosts. Will definitely stay again. "
Windsong Guest Apartments

Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!

10.0 out of 10, Exceptional, (113)
"Truly enjoyed our stay. "
Welcome To Paradise 'AAA' - OCEANFRONT Private Romantic Getaway!

Stunning sunsets, turtle watching, longtails wheeling and glow worms ....

9.8 out of 10, Exceptional, (161)
"Spent 4 nights at the cottage and had a great trip. The location can’t be beat. We used the paddle boards and kayak daily. The host Christine was super helpful even picking up our grocery order. We can’t wait to go back! "
Stunning sunsets, turtle watching, longtails wheeling and glow worms ....

Paradise at Limehouse

9.4 out of 10, Exceptional, (38)
"The room clean and comfortable."
The price is NZ$387
includes taxes & fees
17 Sept - 18 Sept
Paradise at Limehouse

LOCATION! LOCATION! on Bermuda's Gold Coast of beautiful Beaches & Restaurants

10.0 out of 10, Exceptional, (144)
"⭐️💌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"
LOCATION! LOCATION! on Bermuda's Gold Coast of beautiful Beaches & Restaurants

Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course

10.0 out of 10, Exceptional, (122)
"This beautiful home truly exceeded all our expectations. Totally equipped with everything we needed. Amazing host who went above and beyond to be sure everything was perfect! The pictures are beautiful but it is even more spectacular in person. The rooms are huge and it is such a thoughtful layout. The deck is amazing with incredible biews of horshoe bay. Cannot wait to return!"
Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course

Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment

10.0 out of 10, Exceptional, (91)
"This place is fabulous, just like in the pictures. You get your private balcony to watch the sunsets, and walk right down to the ocean for swimming and snorkeling. The owners are super nice and very helpful. The is room comfy and the bed is nice and firm. We would definitely stay here again. Small word of awareness, it is down a steep road, and can be tricky to navigate. Also it requires some up and down hilly walking to the ocean and room, just keep that in mind. Other than that, it's paradise,...
Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment

Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!

10.0 out of 10, Exceptional, (40)
"Overall a very nice property. We like to be off the beaten track and it certainly was."
Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!

Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style

9.2 out of 10, Wonderful, (38)
"I am local and I booked this cottage for family visiting for the first time. The location is across the street from my childhood beach. This made for some very happy visitors! The large window in the living room is gorgeous and was perfect for unwinding next to or watching thunderstorms. The kitchen was clean and stocked with everything you would need. The property is along a main bus route and just a few minutes away from some of my favourite restaurants, a wonderful nature preserve, and a...
Beach House Chateau West SLEEPS 5- 2 Bed 1Bath Bermy Style

Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!

9.8 out of 10, Exceptional, (126)
"the views are breath taking house needs some work but being on the water will beat any property up"
Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!

[A]MOUR AMOUR AMOUR The Heart of Hospitality

9.8 out of 10, Exceptional, (15)
"Amour is an amazing place to stay, exactly as described in the listing (actually even better). The Location is fantastic, easy access to restaurants and a short walk to the railway trail or the beach. I can't say enough about the host, Claudette goes out of her way to make you feel at home and is available for whatever you may need! I highly recommend staying with Claudette at Amour! I will always try to book her place when I return to Bermuda! "
[A]MOUR AMOUR AMOUR The Heart of Hospitality

Spacious Beachfront and Private Resort living

9.8 out of 10, Exceptional, (133)
"Will be back for sure !Would give 6 stars if possible !!!Lorna was an amazing host & made us feel like family "
Spacious Beachfront and Private Resort living

3 bedroom home with pool

10.0 out of 10, Exceptional, (8)
"Charming family home kept extremely clean with fantastic kitchen & utensils. Very comfortable beds, great AC, large rooms with fabulous storage. Lovely host / family."
3 bedroom home with pool

Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!

9.8 out of 10, Exceptional, (96)
"We loved our time at this property! The unit was beautifully setup, amazing view all day long, convenient access to bus, walkable to beach and Breezes restaurant. And to top it off the host is great too and even coordinated our transportation to and from airport. Highly recommend! "
Private and Dreamy.....Balcony, Wine, Sunset, Upstairs with its own entrance!

Private Beach at the Cliffs of Marley - Studio - Bit of Heaven

9.8 out of 10, Exceptional, (45)
"Clean and beautiful! One of the best views in Bermuda! "
Private Beach at the Cliffs of Marley - Studio - Bit of Heaven

Brand New, modern, light, delightful small apartment packed with luxuries

9.2 out of 10, Wonderful, (25)
"Love it! It was great staying here. Patrick was amazing & attentive. Definitely coming back!"
Brand New, modern, light, delightful small apartment packed with luxuries

Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.

9.8 out of 10, Exceptional, (98)
"Sand Dollar was exactly what we needed for our week in Bermuda - amazing beach & accommodations and great access to the bus line too "
Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.
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

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$387 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?

Your Private Luxury Villa - 3 Bedrooms, House & Cottage, Pool, Walk to Beach! : This holiday home rental outside of 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 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.