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Vacation rentals in Caledon

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Top-rated vacation rentals in Caledon

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

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Top guest favorite
A small balcony features a round table with a yellow mug and a jar. Two wooden chairs are nearby, and a blanket is draped over one. The scene includes a view of the sea through a wide opening, enhancing the relaxing atmosphere.
Apartment in Hermanus
4.95 out of 5 average rating, 509 reviews

Westcliff Balcony Room

Welcome to this serene and spacious upstairs apartment - with a pool on the one side and a balcony with amazing sea view on the other side. The room itself is warm, cosy and arty. There is plenty of storage, places to sit and relax, access to the pool and safe off street parking. What I love about the room is the feeling you get when you're there... it seems to say 'you're on holiday.. relaaaaxx'. Other 2 apts on the property: /h/westcliff-pool-room-hermanus /h/westcliff-garden-room-hermanus

Top guest favorite
Double doors with glass panels open to a cozy lounge area visible through the entrance. A wooden deck features a dining table with chairs, surrounded by lush greenery that provides a sense of privacy.
Apartment in Onrus River,
4.98 out of 5 average rating, 192 reviews

Oak & Owl Self-catering Cottage

Come see the whales and taste the wine! Romantic, self-catering cottage with quality finishes in secure estate, Onrus – 30 min walk to beach. Nestled among trees, safe, private, own entrance. Sleeps 2 adults in en-suite bedroom + 2 adults/children on bunk beds in lounge (no children under 2 years plse). Free sherry & firewood! Wi-fi, DSTV, Netflix, free parking. Sun deck with gas BBQ. Quality linen. Aircon. Markets, wine routes & nature walks. Note: There are stairs. GENERATOR FOR LOADSHEDDING

Guest favorite
A heated Jacuzzi with jets is positioned on a private deck, offering expansive views of the sea and surrounding landscape. The wooden structure is complemented by a small side table, with the horizon stretching into the distance under a clear sky.
Guest suite in Vermont
4.84 out of 5 average rating, 303 reviews

Kersbos penthouse situated in Vermont Hermanus

This private unit is situated in Vermont Hermanus, the top floor of a 3 storey house, where you have seaviews on the one side and mountain views on the other. We are 900 m from the well known walkways and about 1.2 km from Davies Pools. 10 km from city centre. There are wine farms, golf courses, fishing, whale watching, hiking trails, art galleries, good restaurants amongs other thing to visit . Wake up to the sound of breaking waves. Sunrise and sunsets are something to enjoy from the stoep. .

Top guest favorite
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, 104 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 favorite
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, 115 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 favorite
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
4.93 out of 5 average rating, 176 reviews

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 favorite
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, 139 reviews

Treyntjes River 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

Guest favorite
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, 265 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 favorite
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, 120 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 favorite
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, 374 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 favorite
The spacious room features a queen bed with a decorative headboard and crisp linens. A kitchenette area is visible in the background, equipped with a microwave and bar fridge. Natural light enters through the windows, highlighting a seating area with wicker chairs.
Guest suite in Hermanus
4.98 out of 5 average rating, 675 reviews

BOUTIQUE ROOM 1 lush luxurious cosy Spoil yourself

This room provides the perfect, cosy spot to make your Hermanus stay unforgetable. Spacious with crisp linen and towels, queen bed, coffee kitchenette, microwave, bar fridge and luxury bathroom. Totally separate from the house for privacy with own entrance. Located within walking distance from cliff paths, whale watching spots, restaurants, golf course, beaches, hiking trails, cycling etc. Ideal for couples, business travelers or solo adventurers.

Top guest favorite
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
4.98 out of 5 average rating, 445 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.

Popular amenities for Caledon vacation rentals

When is the best time to visit Caledon?

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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 vacation rentals in Caledon

  • Total vacation rentals

    Explore 70 vacation rentals in Caledon

  • Nightly prices starting at

    Caledon vacation rentals start at € 9 per night before taxes and fees

  • Verified guest reviews

    Over 870 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Caledon vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Caledon rentals

  • 4.5 Average rating

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