Chelston holiday rentals

We found 231 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Chelston that are perfect for your trip. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, including parking and a garden. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Chelston

Showing deals for:20 Nov - 27 Nov

Dining
Exterior
Interior
Family Room
Exceptional
(9 reviews)

Luxurious 4 Bedroom Oceanside house with pool

Sandys Parish

9% off
AU$13,517
for 7 nights, 1 home
AU$1,931 per night
includes taxes & fees
Luxurious 4 Bedroom Oceanside house with pool
Patio
Sound Winds from Harrington Sound
Sitting Room
Sitting Room
Exceptional
(12 reviews)

Sound Winds 5 bedroom waterfront estate w tennis court

Hamilton Parish

9% off
AU$21,210
for 7 nights, 1 villa
AU$3,030 per night
includes taxes & fees
Sound Winds 5 bedroom waterfront estate w tennis court
Living area
Private kitchen
Interior
Room
Exceptional
(8 reviews)

Charming 1-bedroom apartment centrally located to all that Bermuda has to offer

Devonshire Parish

9% off
AU$2,067
for 7 nights, 1 apartment
AU$295 per night
includes taxes & fees
Charming 1-bedroom apartment centrally located to all that Bermuda has to offer
Stairs leading to upper patio deck and wheelchair accessibility leading to pool
View of wheelchair accessibility walkway from upper patio deck
Spacious Bathroom
Spacious living and dining areas - 3rd and/or fourth guests will sleep here
Exceptional
(9 reviews)

'RIPPLE WATERS' - More for Less - Great One Bedroom Pool House

Southampton Parish

9% off
AU$3,164
for 7 nights, 1 apartment
AU$452 per night
includes taxes & fees
'RIPPLE WATERS' - More for Less - Great One Bedroom Pool House
Living Room.
Dining
Island feel bedroom. with queen bed
Kitchen, indoor dining table/island plus everything you need.
Exceptional
(6 reviews)

New! Rennovated 1-bedroom condo. Walk to beach & waterfront restaurants.

Town of St. George

8% off
AU$4,004
for 7 nights, 1 apartment
AU$572 per night
includes taxes & fees
New! Rennovated 1-bedroom condo. Walk to beach & waterfront restaurants.
view from bed in bedroom on a rainy day
Tucker's Point golf course less than a 5-minute ride away
serene, peaceful, tranquil, HIDDEN OASIS
unobstructed water views + yard space
Exceptional
(24 reviews)

Hidden Oasis • Tucked Away • Unobstructed Water Views • East end

Hamilton Parish

9% off
AU$2,210
for 7 nights, 1 apartment
AU$316 per night
includes taxes & fees
Hidden Oasis • Tucked Away • Unobstructed Water Views • East end

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Chelston getaway

Learn about the unique charm of Chelston with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Chelston

Do you want to discover attractions to visit while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Chelston a one-of-a-kind holiday spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Fairmont Southampton Golf Club (3.3 mi / 5.2 km)
  • Bermuda Aquarium Museum and Zoo (BAMZ) (4 mi / 6.5 km)
  • Bermuda Fun Golf (4.7 mi / 7.6 km)
  • Port Royal Golf Course (5.6 mi / 9 km)
  • Tucker's Point Golf Club (6.2 mi / 10 km)
  • Mid Ocean Golf Club (6.3 mi / 10.1 km)

Exploring the natural landscape of Chelston

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Chelston is a great spot to appreciate mother nature. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Elbow Beach (0.5 mi / 0.7 km)
  • Bermuda Botanical Gardens (1.4 mi / 2.3 km)
  • Warwick Long Bay (2.1 mi / 3.3 km)
  • Horseshoe Bay (3 mi / 4.8 km)
  • Church Bay (4.4 mi / 7 km)
  • Black Bay Beach (4.6 mi / 7.5 km)

Travelling to and around Chelston

Fly into St. George's (BDA-L.F. Wade Intl.), the closest airport, located 7.3 mi (11.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Chelston when booking a holiday rental?
When considering a holiday rental in Chelston, Bermuda, the area offers a delightful blend of tranquillity and accessibility. One of the more appealing neighbourhoods is near the waterfront, where you're treated to stunning views of the ocean and easy access to serene beaches. The proximity to popular attractions such as the Bermuda Aquarium, Museum and Zoo makes it an ideal spot for families and nature enthusiasts alike.In terms of available properties, Chelston features a variety of options, from charming villas to modern apartments, suiting different tastes and budgets. The sense of community in this area is complemented by local amenities, including quaint cafes and shops, creating an inviting space for visitors.
What are the top attractions in Chelston?
In Chelston, Bermuda, visitors can enjoy a variety of attractions that showcase the island's natural beauty and cultural heritage. The nearby Elbow Beach is renowned for its soft pink sands and crystal-clear waters, providing an idyllic setting for sunbathing and water sports. For those interested in history, the National Museum of Bermuda, located in the nearby Dockyard area, offers fascinating exhibits detailing the island's maritime past.The charming streets of Chelston are lined with pastel-coloured homes and lush gardens, creating a picturesque environment for leisurely strolls. Additionally, the area is close to the stunning Botanical Gardens, where visitors can explore a diverse collection of tropical plants and enjoy tranquil walking paths. Golf enthusiasts may also appreciate the proximity to the esteemed Mid Ocean Club, known for its challenging course and breathtaking ocean views.
Are all fees included in the Chelston holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chelston holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chelston with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chelston holiday homes?
You can find great discounts on holiday homes in Chelston on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chelston holiday home booking on Stayz?
To find Chelston holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chelston?
A long-stay holiday home in Chelston is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chelston holiday home?
Book your Chelston holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chelston?
Prices for holiday homes in Chelston vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chelston to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.