
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.

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

the forest chalet - Sondagskloof
Built from Larch & Spruce cured to a dark finish, this secluded one bed-roomed chalet blends into the surrounding Poplar forest nestled next to a running stream. A King size bed, a luxurious bathroom with sliding door onto deck for a indoor/outdoor shower experience. The living-room/ kitchen is stylishly furnished & is fully equipped, with under counter fridge & gas hob, and a wood burning fireplace. Big picture windows & sliding doors open onto the deck, drawing the peaceful forest inside.

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.

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.

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.

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.

Ferrybridge river house
FERRYBRIDGE HOUSE Loadshedding proof • pet friendly • family friendly • remote work friendly • ideal for birdwatchers • not ideal for parties • not available over Christmas and New Years. Located right on the river with sweeping views, our beloved family holiday home is ideal for family getaways, bridal parties, gatherings with friends, business retreats, and quiet weekends away. Please note we only accept guests over 24 y/o, with prior reviews and a 4.5+ rating.

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.

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

Vineyard House
30km outside Worcester (towards Villiersdorp) The perfect romantic getaway in beautiful and tranquil surroundings. Vineyard House is surrounded by a 360° view of vineyards and mountains. We offer a modern, private stay just outside Worcester, approximately 1½ hours drive from Cape Town. Vineyard House offer a 2 bedroom house (sleeps 4), a bathroom, fully furnished kitchen, livingroom with a fire place and a stoep looking onto the vineyards.

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.

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.
Popular amenities for Caledon vacation rentals
Other great vacation rentals in Caledon

The Otters Oarsman / Stanford Riverside Retreat

Dithe Rosemary Hut

FARMHOUSE @ Porcupine Hills Guest Farm

Upper Mountain Cottage

Hermanuspietersfontein Posmeester Cottages

Seaview Container Studio

Heart & Soul

Rolling Hills Farmstead 2 BR Eco-Chalet
Quick stats about vacation rentals in Caledon
Total rentals
70 properties
Nightly prices starting at
R174 ZAR before taxes and fees
Total number of reviews
870 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Frequently Asked Questions
How much does it cost to stay in guesthouse rentals in Caledon?
Experience the best of Caledon with our guesthouse rentals, starting at about $30 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 bed and breakfast rentals in Caledon have free parking?
Absolutely! We offer over 10 bed and breakfast rentals with free parking in Caledon. Enjoy a tailored experience with all the comforts you desire.
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.
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.
Destinations to explore
- Cape Town Vacation rentals
- Plettenberg Bay Vacation rentals
- Hermanus Vacation rentals
- Langebaan Vacation rentals
- Stellenbosch Vacation rentals
- Knysna Vacation rentals
- Franschhoek Vacation rentals
- Southern Suburbs Vacation rentals
- Mossel Bay Vacation rentals
- Betty's Bay Vacation rentals
- George Vacation rentals
- Breerivier Vacation rentals
- Babylonstoren
- Waterkloof Wine Tasting Lounge
- Erinvale Estate Hotel and Spa
- Jonkershoek Nature Reserve
- Voëlklip Beach
- Idiom Restaurant & Idiom Wine Tasting Centre
- Worcester Golf Club
- Grotto Beach (Blue Flag)
- Bugz Family Playpark
- Fernkloof Nature Reserve
- De Zalze Golf Club
- Cavalli Estate
- Paserene Wine Farm & Wine Tasting in Franschhoek
- Arabella Golf Club
- Die Plat
- Agulhas National Park
- Grotto Beach
- Haut Espoir
- Die Gruis
- Nederburg Wines
- Vergenoegd Löw The Wine Estate
- Tokara Wine Estate
- Warwick Wine Estate
- Quoin Rock