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Holiday houses in Caledon

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Top-rated holiday rentals in Caledon

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

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Top Guest favourite
A private boma area features a fire pit surrounded by colorful rock formations and shrubs. Two lounge chairs with striped cushions face a small table set with wine glasses, offering a scenic view of the distant mountains under a softly lit sky.
Guest suite in Sir Lowry's Pass
5 out of 5 average rating, 257 reviews

Intaba Studio Tranquil Getaway w/style & character

An ideal escape, our Studio is a private, self-catering garden unit located on the mountainside on a 300 Ha farm , with a pool (shared), & beaches closeby (15 min). Off the Grid - own power supply & fresh spring water extracted high in the mountains. Panoramic views over sea and mountain landscapes , surrounded by fynbos and wild birdlife , close to Capetown (55 km), airport, (40km) shopping amenities (7km) . Unwind after a busy day and relax at your private boma or around the pool.

Top Guest favourite
Large glass doors open to a serene view of a natural pond, framed by soft drapes. A cozy seating area is visible, with a plush sofa adorned with neutral cushions. Outside, a small bistro table and chairs are positioned on the lawn, enhancing the tranquil setting.
Farm stay in Worcester
4.99 out of 5 average rating, 102 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
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
5 out of 5 average rating, 110 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

Guest favourite
A wood-fired hot tub is positioned on a wooden deck, overlooking expansive views of the rolling hills and valleys below. The cloudy sky adds depth to the landscape, while greenery borders the foreground, creating a serene environment.
Home in Overberg District Municipality
4.94 out of 5 average rating, 174 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.

Top Guest favourite
A modern tiny home is nestled among trees, showcasing its sleek exterior with a corrugated design. Large glass windows reflect the surrounding greenery, while a wooden deck accommodates outdoor seating. Lush grass and plants frame the structure, creating a serene forest setting.
Tiny home in Baardskeerdersbos
4.96 out of 5 average rating, 142 reviews

Cosy Forest-Tinyhouse with fireplace.

Nestled in a poplar forest, this tiny home is perfect for a couple wanting to venture into the platteland & escape their daily routines. Sheltered in the summer by a lush canopy, in winter, stripped bare, inviting in the blue skies. In stormy cold weather a combustion oven works it's magic warming "THE TINY" making for cosy winter cuddling! The small forest forms part of LOKAL, a 1ha property, with an vegetable garden , Orchards of fruit & nuts, some chickens & the Garden Cottage.

Guest favourite
The open-plan lounge and dining area features a central wooden table surrounded by classic chairs. A cozy seating arrangement with woven chairs sits beside a rustic broom. Light enters through windowpanes, illuminating the clay-tiled floor and highlighting the textural elements of the thatched-roof interior.
Cottage in Greyton
4.86 out of 5 average rating, 263 reviews

Potato Patch Self Catering Cottage

This versatile thatched roofed cottage is centrally located in a private setting offering contemporary country comfort with a dash of history. It is one of the two cottages located on the owners property with its own entrance and secluded garden. The cottage consists of 3 en suite bedrooms furnished with king sized beds. The rates are based on 2 people sharing a room. Using additional rooms comes with an additional charge. Pets are permitted on request at an additional charge.

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, 116 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 small bird with bright yellow-green plumage is perched above its nest, surrounded by vibrant green foliage. Two chicks with open beaks can be seen in the nest, nestled within soft twigs and leaves, awaiting nourishment from their parent.
Guest suite in Stanford
4.96 out of 5 average rating, 373 reviews

Studio suite, kingsize bed, private garden

Escape to a wonderland of rural tranquility. The Bird House is perfect for a weekend getaway, Garden Route stopover or longer stay for touring the Overberg-Hermanus area. Nestled in its own private garden, the stylish suite offers a well-equipped kitchenette, cosy seating & table for eating/work. Relax in the private bird-filled garden, enjoy a braai & experience starlight quiet. Convenient proximity to wedding venues, wine & cheese farms & places for fine food.

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
4.95 out of 5 average rating, 137 reviews

Treyntjes River Cottages

Treyntjes Rivier Cottages are about 9 km from Caledon and 25 km from Hermanus. The cottage offer accommodation for up to 4 guests. The cottage consist of 2 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, TV and WIFI Braai facilities are available in the garden. Please note: no day visitors are allowed

Top Guest favourite
The cottage features a modern design with a sturdy grey exterior and a sloped roof. A covered porch with comfortable seating invites relaxation. Lush green grass surrounds the structure, complemented by neatly trimmed bushes. A warm sunset casts a gentle glow over the setting.
Farm stay in Stellenbosch
4.97 out of 5 average rating, 439 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.

Top Guest favourite
A spacious lawn extends from a modern garden annex, bordered by neatly trimmed hedges. Large windows reflect the sky, while a wooden bench under a leafy tree offers a serene spot to relax. The backdrop features rolling hills and distant mountains.
Farm stay in Elgin
4.99 out of 5 average rating, 106 reviews

Best Elgin views in serene setting with pool

The Annex at Tree Tops, is a spacious and well-appointed garden annex with incredible views, adjoining the main homestead. This is the perfect couples’ retreat in which to recharge your batteries while overlooking the magnificent Elgin valley. Offering a wood-burning fireplace (free wood provided) for winter and a plunge pool for summer.

Top Guest favourite
A large window offers a panoramic view of the surrounding mountains and ocean, reflecting the vibrant blue sky with scattered clouds. The glass showcases a glimpse of the interior, with cozy cushions visible on a nearby seating area.
Loft in Pringle Bay
4.94 out of 5 average rating, 274 reviews

Dreamcatcher

Dreamcatcher House and its "Above"is a wonderful Place to enjoy Nature and Life around a little magical place called Pringle bay. Between the ocean, the mountains and the sky lies plenty of opportunity to live the moment and create unforgettable memories. Pringle bay, our house and "Above" are looking forward to host and meet you.

Popular amenities for Caledon holiday rentals

When is the best time to visit Caledon?

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Avg. price$99 NZD$95 NZD$95 NZD$99 NZD$104 NZD$97 NZD$99 NZD$99 NZD$114 NZD$95 NZD$93 NZD$95 NZD
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Frequently Asked Questions

  • How much does it cost to stay in bed and breakfast rentals in Caledon?

    Experience the best of Caledon with our bed and breakfast rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

  • Do guesthouse rentals in Caledon have free parking?

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

  • Do bed and breakfast rentals in Caledon have wifi?

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

  • 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.

  • What are the most popular amenities for Bed And Breakfast Rentals in Caledon?

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

  • 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 80 vacation rentals in Caledon, over 70 vacation rentals in Middleton, and over 80 vacation rentals in Bergsig.

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 $18 NZD per night before taxes and fees

  • Verified guest reviews

    Over 870 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Caledon holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Caledon rentals

  • 4.5 Average rating

    Caledon stays receive an average rating of 4.5 out of 5 from guests