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Holiday rentals in Caledon

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Caledon

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A cozy living area features a large window with sliding glass doors opening to a serene view of the pond. Natural light floods the space, highlighting the textured curtains and woven pendant lights. A plush sofa is complemented by a patterned rug and indoor plants.
Farm stay in Worcester
4.98 out of 5 average rating, 146 reviews

Lily Pond

Lily Pond, is a luxurious guest house just an hour and a half from Cape Town. Lily Pond is set on a natural pond brimming with incredible bird life, creating a serene atmosphere unmatched anywhere else. With no other cottages in sight and located on a picturesque wine farm, it offers a rare blend of privacy and luxury. The indulgent outdoor bath overlooking the pond, combined with the beautiful walking trails, enhances the sense of peace and seclusion, making this retreat truly one of a kind.

Top guest favourite
Home in Stanford
4.96 out of 5 average rating, 167 reviews

Ferrybridge river house

FERRYBRIDGE HOUSE Loadshedding proof • pet friendly • family friendly • remote work friendly • ideal for birdwatchers • not available over public holiday weekends, Christmas and New Years. Located right on the river with sweeping views, our beloved family holiday home is ideal for family getaways, gatherings with friends, business retreats, and quiet weekends away. Please note we don’t accommodate parties, and only accept guests over 25 years of age, with prior reviews and a 4.5+ rating.

Top guest favourite
A wooden deck features a hanging swing chair overlooking expansive views of the landscape and mountains beyond. A wood-fired hottub is visible, with steam rising gently into the air, and modern outdoor furniture is arranged for relaxation.
Cabin in Riviersonderend
4.98 out of 5 average rating, 148 reviews

Ribbok

Ribbok is situated on a working farm in the Overberg Area. Surrounded by beautiful Renosterbos veld overlooking the Riviersonderend Mountains. Modern self-catering unit that includes the following: Single Bedroom with king size bed Bathroom with shower, toilet, basin Fully equipped kitchen fitted with a gas stove, fridge, microwave, airfryer, toaster, cutlery,crockery Coffee, tea, sugar are provided Free wifi Airconditioning Large deck Wood-fired hottub Braai facilities Fire Wood is provided

Top guest favourite
A stunning view of mountain peaks is captured at sunset, revealing warm hues illuminating the rocky surfaces. The foreground features a wooden deck with a soft, light-colored fabric draped over a chair, enhancing the serene atmosphere surrounding the cabin.
Cabin in Stellenbosch
5 out of 5 average rating, 116 reviews

Camissa farm. Gorgeous views and a Hottub too!

This stylish and romantic cabin for 2 floats over the Banhoek valley and enjoys exquisite mountain views of outstanding natural beauty. It is the newest in our collection of 6 private serviced eco cabins on a beautiful 60 hectare regenerative farm in the Banhoek nature conservancy. There are hiking trails for you to explore, a hot tub and infra red sauna to luxuriate in and wild swimming to enjoy. Refresh your soul in this natural paradise and renew your connection with nature and yourself.

Top guest favourite
The living area features comfortable seating with decorative cushions, a natural fiber coffee table, and warm wooden beams overhead. Floor-to-ceiling glass doors provide expansive views of the surrounding vineyards and mountains, while light enters freely from the open space.
Earthen home in Stanford
4.99 out of 5 average rating, 100 reviews

Vineyard Cottage | Goodluck Homestead

Off-grid eco cottage situated on a working regenerative farm in the heart of the Overberg, with panoramic views towards Walker Bay and the Kleinriviersberg mountains. Surrounded by fynbos and vineyards, this cottage has pure spring fed water, a wood fired hot tub, solar power so is not affected by load shedding. Guests are welcome to wander around the farm, swim and fish in the dams, and meander through the veggie gardens We regret no babies, children or pets are allowed for safety reasons.

Guest favourite
The interior of a contemporary unit reveals large glass windows showcasing expansive views of rolling hills and farmlands. A wooden dining table is positioned near the windows, complementing a cozy wood-fired braai area. A wood-fired hot tub, framed by stone, invites relaxation.
Home in Overberg District Municipality
4.93 out of 5 average rating, 207 reviews

Berseba The Buchu Box

Welcome to The Buchu Box, a contemporary self-catering unit nestled within an essential oils farm, offering breathtaking vistas of the picturesque Overberg in Western Cape. This eco-friendly pod promises a luxurious retreat suitable for couples, solo travelers, and families seeking an escape. Indulge in the epitome of relaxation with our wood-fired hot tub, providing a serene oasis with panoramic views that will leave you spellbound. We have a carbon copy of this unit, The Peppermint Box.

Guest favourite
Home in De Kelders
4.94 out of 5 average rating, 133 reviews

Oceanfront Villa 4br/4ba pool wifi, solar power

Whale Huys is a Self-catering, direct oceanfront villa with panoramic views of Walker Bay and the Klein Rivier Mountains. Perfect for a relaxing holiday away, just 2 hours from Cape Town. With its stunning views and just the sounds of nature, Whale Huys seems far removed from the busy hustle and bustle of our daily lives. but is close to the wineries and renowned country restaurants the area is famous for. Outdoor and cultural activities abound. Just 5 min. from Gansbaai for shopping.

Guest favourite
An outdoor stoep features a fire pit surrounded by a stone enclosure and a comfortable sofa. Warm light from the fire contrasts with the evening sky, while glass doors offer a view into the open-plan kitchen and lounge area.
Cottage in Sandbaai
4.99 out of 5 average rating, 134 reviews

Cosy Seaside Cottage | Hot Tub & Fire Pit

A neat comfortable flat in a peaceful neighbourhood, a 500m walk away from the Onrus to Sandbaai coastal path. Great locations for swimming, surfing, diving or just catching some sun rays. If you like mountain biking or hiking the mountains are also just around the corner. The stoep features a wood fired hot tub and fire pit and looks towards the mountains and a stand of bluegums which attracts a lot of bird life. The flat is on our property but is completely separate with secure parking.

Top guest favourite
An outdoor area features a hexagonal hot tub surrounded by grassy space. A picnic table with benches is positioned beneath a large umbrella, while a braai area with a grill stands nearby, offering a scenic view of the surrounding landscape.
Cottage in Caledon
4.94 out of 5 average rating, 157 reviews

Treyntjes Rivier Cottages

Treyntjes Rivier Cottages are about 9 km from Caledon and 25 km from Hermanus. It can accommodate up to 4 persons Two bedrooms each with their own en-suite bathroom. The main bedroom with a king size bed, the second bedroom with 2 single beds. The kitchen is fully equipped and the living area offers couches, Smart TV and WIFI Braai facilities are available in the garden. We no longer allow brides or grooms to get ready at our cottages on the day of their wedding. No day visitors

Top guest favourite
A rustic exterior view of a cottage features large wooden sliding doors surrounded by vibrant greenery. A stone path leads to the entrance, with well-maintained flower beds flanking the sides, complemented by a modern roof and solar panels overhead.
Cottage in Cape Winelands District Municipality
4.99 out of 5 average rating, 152 reviews

Heidi's Barn, Franschhoek

Situated on a small holding 5km outside Franschhoek, opposite the exquisite La Motte Wine Estate, Heidi’s Barn offers the perfect self-catering base from which to explore the Winelands. A fire pit, outdoor dining area and a large swimming pool (shared with one other cottage) are perfect for summertime relaxation while an indoor wood-burning fireplace and wooden floors throughout make for a cosy winter escape. The barn runs on mains power with solar back up for load shedding.

Top guest favourite
A modern freestanding bathtub is positioned within a wooden structure, partially hidden by lush green foliage. Natural light filters through slatted walls, creating a serene and tranquil space.
Farm stay in Stellenbosch
4.98 out of 5 average rating, 500 reviews

Romantic cottage with a pool AND an open air tub!

RiverStone Cottage lies at the foot of the majestic Simonsberg mountain with panoramic views in all directions. Whether you are relaxing under vast oaks or at the plunge pool and watching the sunset turn the mountains pink or are an early bird and watching the sun rise behind cheeky, pointed Botmanskop, there are moments aplenty to ooh and aah at the majesty that surrounds this very special place.

Guest favourite
A modern pod is positioned on a gentle slope overlooking a serene body of water. Surrounding hills frame the landscape, while patches of burnt vegetation indicate recent changes. The sky above is overcast, contributing to a calm atmosphere.
Shipping container in Villiersdorp
4.95 out of 5 average rating, 102 reviews

Exquisite panoramic one bedroom Mountain Eco Pod

Enjoy panoramic views in your own romantic slice of nature. Kitted out with your own wood-fired hot tub, luxurious down bedding & high thread count white linen, it’s the perfect romantic getaway. Situated on the mountain above an apple and pear farm on the edge of the Theewaterskloof.

Popular amenities for Caledon holiday rentals

When is the best time to visit Caledon?

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Avg. price$93 SGD$94 SGD$87 SGD$72 SGD$75 SGD$70 SGD$72 SGD$72 SGD$83 SGD$84 SGD$84 SGD$91 SGD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Caledon?

    Caledon has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Caledon?

    Experience the best of Caledon with our apartment rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Caledon?

    Yes! Work meets play with ease at over 30 vacation rentals in Caledon featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Caledon vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Caledon, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Caledon?

    Make yourself at home in Caledon by choosing from our most frequently booked neighborhoods. We have over 70 vacation rentals in Caledon, over 70 vacation rentals in Middleton, and over 70 vacation rentals in Bergsig.

  • Do guesthouse rentals in Caledon have wifi?

    Absolutely! We offer over 10 guesthouse rentals with wifi in Caledon. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Caledon have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Caledon. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Guesthouse Rentals in Caledon?

    Enhance your stay in our Guesthouse Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Caledon

  • Total holiday rentals

    Explore 70 holiday rentals in Caledon

  • Nightly prices starting at

    Caledon holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 980 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Caledon holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Caledon rentals

  • 4.6 Average rating

    Caledon stays receive an average rating of 4.6 out of 5 from guests