Chelston holiday homes

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

Family Room
Exterior
Interior
Dining
Exceptional
(9 reviews)

Luxurious 4 Bedroom Oceanside house with pool

Sandys Parish

9% off
NZ$16,225
for 7 nights, 1 home
NZ$2,318 per night
includes taxes & fees
Luxurious 4 Bedroom Oceanside house with pool
Sitting Room
Sound Winds from Harrington Sound
Patio
Gym with Tempo.fit
Exceptional
(12 reviews)

Sound Winds 5 bedroom waterfront estate w tennis court

Hamilton Parish

9% off
NZ$25,658
for 7 nights, 1 villa
NZ$3,665 per night
includes taxes & fees
Sound Winds 5 bedroom waterfront estate w tennis court
Interior
Private kitchen
Room
Living area
Exceptional
(8 reviews)

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

Devonshire Parish

9% off
NZ$2,439
for 7 nights, 1 apartment
NZ$348 per night
includes taxes & fees
Charming 1-bedroom apartment centrally located to all that Bermuda has to offer
Spacious Bathroom
View of wheelchair accessibility walkway from upper patio deck
Spacious living and dining areas -
3rd and/or fourth guests will sleep here
Enjoy a refreshing dip in our 20'x40' pool! There's also a gas BBQ grill.
Exceptional
(9 reviews)

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

Southampton Parish

9% off
NZ$3,817
for 7 nights, 1 apartment
NZ$545 per night
includes taxes & fees
'RIPPLE WATERS' - More for Less - Great One Bedroom Pool House
Island feel bedroom. with queen bed
Dining
Kitchen, indoor dining table/island plus everything you need.
Living Room.
Exceptional
(6 reviews)

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

Town of St. George

8% off
NZ$4,924
for 7 nights, 1 apartment
NZ$703 per night
includes taxes & fees
New! Rennovated 1-bedroom condo. Walk to beach & waterfront restaurants.
serene, peaceful, tranquil, HIDDEN OASIS
Tucker's Point golf course less than a 5-minute ride away
view from bed in bedroom on a rainy day
living room with sofa, armchairs, and twin bed
Exceptional
(24 reviews)

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

Hamilton Parish

9% off
NZ$2,611
for 7 nights, 1 apartment
NZ$373 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

Why visit Chelston

  • Picturesque Beaches: Chelston boasts stunning coastal spots perfect for sunbathing and swimming, ideal for a relaxed getaway.
  • Vibrant Urban Parks: Enjoy family-friendly picnics and leisurely strolls in well-kept urban parks.
  • Charming Streets: Wander through dynamic streets that capture the local culture and history.
  • Quaint Architecture: Admire high-ceilinged, romantic buildings that add unique character to the village.
  • Outdoor Adventures: Embrace a blend of coastal walks and urban exploration for an active holiday.

Top attractions near Chelston

Chelston, Paget Parish, Bermuda offers a blend of outdoor adventures and urban explorations. Visitors can enjoy its picturesque beaches, vibrant streets, and welcoming urban parks, perfect for family outings or a cultural day out. Whether you're relishing a coastal stroll or exploring the city's dynamic culture, Chelston provides a refreshing escape with plenty of local charm for every traveller.

  • Marley Beach: A coastal haven with a relaxed beach vibe, perfect for soaking up the sun and enjoying the soothing sounds of the ocean, all within 1.6km from Chelston.
  • Bermuda Society of Arts: An arts centre celebrating culture and creativity, offering local exhibitions and creative workshops, located 1.6km away from Chelston.
  • Perot Post Office: A charming historic building, rich in cultural heritage and local stories, just 1.6km from Chelston.

Things to do recommended for couples

Looking for a romantic getaway in Chelston, Paget Parish? Enjoy a sunset stroll along the stunning South Shore beaches or indulge in a candlelit dinner at a local restaurant. Don't miss a scenic bike ride through lush landscapes, perfect for creating unforgettable memories together.

Things to do recommended for families

Families will enjoy exploring the charming streets of Chelston and the scenic coastal paths, as well as engaging in interactive local activities designed for kids. Discover the authentic Bermudian experience during your stay in Paget Parish.

Things to do recommended for groups

Groups visiting Chelston can enjoy a delightful day at the beautiful Horseshoe Bay Beach, indulge in local cuisine at nearby restaurants, and explore the scenic trails of the Bermuda Railway Trail, perfect for a refreshing group hike with stunning coastal views.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chelston

Whether you're travelling with a group, as a family, with your pets, or seeking extended stays, be sure to apply the appropriate filters. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chelston with a group: Think about how many bedrooms you'll require, as well as any amenities like a fully equipped kitchen or outdoor space for group activities. The good news is that you can easily filter for these options and more on Vrbo.
  • Traveling to Chelston with young kids: Traveling with little ones can be demanding. It’s important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. It’s also wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Chelston: For many, a family holiday isn’t complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring everyone feels at home.
  • Planning for a long term stay visiting Chelston: If you're in search of holiday rentals with special offers for stays of a month or longer, you've come to the right spot. By using the appropriate filters, you can easily discover and save on monthly rentals. Don't forget to consider including options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Chelston

Discover the charm of Chelston, Paget Parish, Bermuda, where you can enjoy the stunning scenery and friendly atmosphere. Explore the beautiful Grape Bay Beach, ideal for sunbathing and swimming, or relax on the large lawns that invite family-friendly picnics. The village features high ceilings in its quaint architecture, adding to the romantic feel, making it a perfect spot for an outdoor getaway. Chelston offers a delightful blend of relaxation and adventure for all visitors.

  • Warwick Parish: Warwick Parish is a vibrant city just 3km from Chelston, offering an enticing blend of beachside charm and outdoor adventure. The scenic bay and family beach provide a perfect backdrop for a range of leisurely pursuits, from playing a round of golf at the local course to simply enjoying the ocean breeze. The area's mix of natural beauty and recreational facilities makes it an appealing destination for travellers seeking both relaxation and active experiences.
  • Paget Parish: Situated in the heart of Paget Parish, Chelston enjoys close proximity to this city, where travellers are drawn to its inviting beaches and stunning outdoor settings. The picturesque bay and family beach offer a scenic retreat, ideal for those looking to unwind or partake in outdoor activities. With golf courses and general recreational spots accessible nearby, Paget Parish provides a balanced mix of nature and leisure opportunities.
  • Hamilton: Only 2km from Chelston, Hamilton promises a refreshing escape with its blend of outdoor and beach experiences. The local attractions, including a beautiful bay and family beach, invite visitors to explore and enjoy leisurely walks along the shore or a round of golf. Hamilton’s close proximity not only provides easy access to its natural scenery but also enhances its appeal as a destination for a relaxed yet engaging holiday experience.

Best time to go to Chelston

If you're planning a trip to Chelston, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January65.8°F (18.8°C)Light RainMostly Cloudy
February64.9°F (18.3°C)Light RainMostly Cloudy
March64.4°F (18.0°C)Light RainMostly Cloudy
April66.6°F (19.2°C)Light RainMostly Sunny
May70.2°F (21.2°C)Light RainMostly Sunny
June75.4°F (24.1°C)Light RainMostly Sunny
July79.5°F (26.4°C)Light RainMostly Sunny
August81.3°F (27.4°C)Light RainMostly Sunny
September79.9°F (26.6°C)Light RainMostly Sunny
October76.3°F (24.6°C)Light RainMostly Sunny
November71.6°F (22.0°C)Light RainMostly Cloudy
December68.2°F (20.1°C)Light RainMostly Cloudy

Booking with Vrbo is a breeze

Are you keen to save on your upcoming holiday? Consider being flexible with your travel dates, as prices can differ. Moreover, extending your stay can often result in considerable savings. To discover the ideal Vrbo property that suits your budget, simply use our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board gives you a dedicated space to kickstart fresh adventures, keep your plans rolling, or review and organise your bookings. Your saved or booked properties are neatly sorted into Potential, Upcoming, or Current Trips. Discover more about Trip Boards at: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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

How much does it cost to rent a holiday home in Chelston?
The average price for a holiday home in Chelston can vary based on factors like length of stay, property type and season. Whether you'd like a sprawling house with room for friends and family or a quaint cottage for just you and your sweetheart, just enter your dates of travel to view stays with amazing value.
How much does it cost to rent a beach house in Chelston?
The average price for a holiday home by the beach in Chelston depends on when you're travelling and the style and size of property you want. You can quickly and easily find prices on Bookabach by entering the dates you'll be travelling. Then use our handy filter tool to choose the number of bedrooms and amenities that you prefer, such as air conditioning, a pool and WiFi.
What are the top attractions for families in Chelston?
Keeping the kids occupied during your Chelston holiday is easy with these top family-friendly attractions:
  • Bermuda Botanical Gardens
  • Masterworks Museum of Bermuda Art
  • Paget Marsh and Nature Reserve
How old do you have to be to rent a holiday home in Chelston?
We recommend checking with the Chelston holiday home you'd like on Bookabach as the age limit differs. However, it's normally 16, 18 or 21.
How long can I rent a holiday home in Chelston for?
How long you can book a holiday home in Chelston is up to the property. Just enter your selected dates to view a list of options offering extended stays. With a range of amenities such as air conditioning and laundries, as well as some offering weekly or monthly discounts, you're sure to get somewhere perfect to call your home away from home in Chelston.

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