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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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Farm stay in Stellenbosch

5 out of 5 average rating, 118 reviews

Stay on a Working Flower Farm in a Modern Home

Soak up the secluded splendor of this modern farmhouse in the Cape Winelands. A new expansive view awaits at every turn—admire one side of the mountain range in the light-filled entrance hall, and take in the other from the spacious sitting room that brings the outdoors in with a full-size maple tree and sliding glass doors. Colorful textiles and eclectic art objects collected from around the world enliven the farmhouse interiors, where leafy greens and flowers fill each room. Take a dip in the outdoor 15m pool, then enjoy a meal near a wood-burning fireplace on the outdoor patio. Modern house with farm interior. Access to all areas including own pool and garden. Open plan kitchen and living areas with access to verandah and vegetable garden. Will be welcome and greeted by myself ,always available by phone or text . The farmhouse is set in a secluded area just a short drive away from the quaint town of Stellenbosch, ripe with many fruit orchards and wine vineyards—some date as far back as the 1650s. Foodies would be wise to pit stop at Foliage, an award-winning restaurant listed as one of the “World’s 50 Best” restaurants. Own transport is recommended, but Uber is available if needed, guests use them often successfully. Gay friendly. Perfectly located.

Farm stay in Stellenbosch

4.99 out of 5 average rating, 154 reviews

Hidden gem in the heart of the winelands..

A little forest in the heart of the Winelands cuddles this secret gem #jangroentjiecottage close to a dam fed by the fynbos covered Helderberg. a Selfcatering hideaway that sleeps two with a fireplace, braai and a woodfired hottub. Within walking distance from Taaibosch, Pink Valley and Avontuur Wine and stud farm. Just across the R44 Ken Forrester Wines is luring. For the outdoor enthusiasts Helderberg provide trails for hiking and mtbiking and our dam covers swimming, rowing and sundowners.

Home in Franschhoek

4.99 out of 5 average rating, 145 reviews

Mongoose Manor, walk to wine estates and town.

This is the most perfect ever listing. Privacy, location, quality. FULLY SOLAR POWERED. Completed by a top designer, breathtaking views of the mountains and wine valley, next to Le Lude champagne estate and restaurant, on an equestrian estate. And under 10 minutes walk to the centre of town, 5 minutes to Le Lude or Haute Cabriere estates, the monument, museum etc. There is even a friendly water mongoose named Tilly who will come to visit! NO CHILDREN of any age allowed, including infants.

Tiny home in Baardskeerdersbos

4.96 out of 5 average rating, 118 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.

Home in Franschhoek

4.99 out of 5 average rating, 101 reviews

Pure opulence in a heavenly setting

In an exquisite continuation of the splendour offered by Paloma in Camps Bay , comes our most ambitious and luxurious project to date. With 5* ratings from the most discerning of guests, now offers a luxurious space for larger groups in the heart of the idyllic village of Franschoek. 1) Location, location, location..., 2) With endless luxury, 3) Four ample bedrooms, all en-suite, 4) Beautiful communal areas, inside and out, including a large pool, 5) A beautiful established garden.

Guest suite in Stanford

4.96 out of 5 average rating, 330 reviews

Studio suite; king or 2 single 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.

Yurt in Bot River

4.97 out of 5 average rating, 240 reviews

Southern Yurts - Private Forest View Yurt

Yurts are a unique weekend escape - in 2018, Southern Yurts brought this memorable getaway experience to the Overberg! At Forest View Yurt you can enjoy the comfort of your own private Yurt, including a well equipped kitchen cabin and bathroom with an outdoor shower. Watch the sun set over the nature conservancy from your elevated sundowner deck, plan a hike or walk on one of our many trails, or just relax in the candle-lit hot tub under the stars.

Vacation home in Overberg District Municipality

4.94 out of 5 average rating, 125 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 travellers, and families seeking an unforgettable 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.

Farm stay in Worcester

4.96 out of 5 average rating, 228 reviews

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.

Cottage in Caledon

4.94 out of 5 average rating, 100 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 5 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 and a sofa bed in the living area. The kitchen is fully equipped and the living area offes couches, TV and WIFI Braai facilities are available in the garden.

Farm stay in Bot River

4.82 out of 5 average rating, 260 reviews

Dithe Rosemary Hut

Welcome to The Rosemary Hut, a charming rustic retreat nestled within an essential oils farm, offering panoramic views of the stunning Overberg in Western Cape. What sets this unit apart is its unique construction, with hay bales forming the inner walls, exuding rustic charm and warmth. This delightful cottage provides the perfect setting for a romantic escape like no other.

Loft in Pringle Bay

4.93 out of 5 average rating, 227 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.

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Popular amenities for Caledon vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Caledon

Cottage in Cape Winelands District Municipality

4.97 out of 5 average rating, 32 reviews

Heidi's Barn, Franschhoek

Shipping container in Villiersdorp

4.88 out of 5 average rating, 33 reviews

Delightful two bedroom luxe eco pod with hot tub

Home in Gansbaai

5 out of 5 average rating, 37 reviews

Ocean Retreat, Romansbaai Beach & Fynbos Estate

Farm stay in Grabouw

5 out of 5 average rating, 39 reviews

Adorable 2 bedroomed lake side cottage on a farm-

Tiny home in Villiersdorp

5 out of 5 average rating, 27 reviews

Little Light House - No Loadshedding/WiFi/Solar/AC

Cabin in Hermanus

4.96 out of 5 average rating, 28 reviews

Picturesque Lagoon Cabin on Klein River Hermanus

Farm stay in Cape Winelands District Municipality

5 out of 5 average rating, 8 reviews

Ouma Celia Cottage

Home in Hermanus

4.95 out of 5 average rating, 19 reviews

Southwinds Estate

Quick stats about vacation rentals in Caledon

Total rentals
60 properties
Nightly prices starting at
R181 ZAR before taxes and fees
Total number of reviews
720 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 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 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 wireless internet?
Absolutely! We offer over 10 guesthouse rentals with wireless internet 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.
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 Middleton, over 70 vacation rentals in Bergsig, and over 70 vacation rentals in Caledon.

Destinations to explore