
Vacation rentals in Caledon
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Top-rated vacation rentals in Caledon
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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

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.

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.

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

BushBaby Cabin
BushBaby Cabin is perfect for a romantic get-away. A log cabin beautifully nestled in the milkwood forest, just 20mins from Hermanus - secluded from the busyness of life. Situated by the Botriver lagoon, with a private path for access, this hidden gem brings you to nature's doorstep. Look out for the roaming wild horses and a variety of bird-life. BushBaby is in Meerenbosch with communal pool, tennis courts and table tennis access. Ideal to catch summer sun or a warm, cozy fire in winter.

Luxury Ocean Front Retreat For Two
Uninterrupted ocean views in one of the most sought after locations. Direct garden access leads to manicured lawns and access to the sea. The town centre is a short drive or a stroll away, with many dining options. The Hermanus Golf Club, a premier 27-hole course, is around the corner. The flat is three bedrooms with ensuite bathrooms, a fully equipped kitchen with a gas stove, open plan lounge. There is a TV with streaming options, uncapped WiFi. Lastly, a 5kW inverter keeps power on 24/7.

Cottage on Fir Hermanus
Superb non-smoking garden cottage at the back of the main house. It sleeps 4 guests in two very luxurious en-suite double bedrooms (Air conditioned) with spacious TV- lounge and small kitchenette. (Well equipped). Expect good quality linen and fluffy towels and unexpected little luxuries. A sparkling pool, free parking and Fibre Wi-Fi on the premises. Guests can enjoy the garden and pool at leisure. It is completely separate and private as only one other person resides in the main house.

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.

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

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.

Berseba 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.

COSY Kaleidoscope cottage, near beach and trials
Welcome to freestanding Kaleidoscope Cottage, nestled among the Hibiscus trees with a private varandah overlooking a 25 m pool. It is part of Wil Ahhh - a private property, 5minutes from Grotto Beach. It is designed to celebrate the outdoor lifestyle of Voëlklip, the beach suburb of Hermanus and its beautiful sea and mountain landscape.
Popular amenities for Caledon vacation rentals
Other great vacation rentals in Caledon

Amiel's Cottage

Stoepsit - 2-bedroom farm cottage

Mayflower Cottage

Seaview Container Studio

Heuningkloof Eco Cottage Greyton

Seafront Villa - Whale Bay Luxury Retreat

Bird's Nest Cottage in Stanford

Rocklands Studio
When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ206 | ﺩ.ﺇ198 | ﺩ.ﺇ198 | ﺩ.ﺇ206 | ﺩ.ﺇ217 | ﺩ.ﺇ202 | ﺩ.ﺇ206 | ﺩ.ﺇ206 | ﺩ.ﺇ239 | ﺩ.ﺇ198 | ﺩ.ﺇ195 | ﺩ.ﺇ198 |
| Avg. temp | 22°C | 22°C | 21°C | 18°C | 15°C | 13°C | 13°C | 13°C | 15°C | 17°C | 19°C | 21°C |
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 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 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.
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.
Quick stats about vacation rentals in Caledon

Total vacation rentals
Explore 60 vacation rentals in Caledon

Nightly prices starting at
Caledon vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

Verified guest reviews
Over 910 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
60 of Caledon vacation rentals include wi-fi 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
Destinations to explore
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- Voëlklip Beach
- Babylonstoren
- Stellenbosch University
- Grotto Beach (Blue Flag)
- Jonkershoek Nature Reserve
- Waterkloof Wine Tasting Lounge
- Idiom Restaurant & Idiom Wine Tasting Centre
- Cavalli Estate
- Fernkloof Nature Reserve
- De Zalze Golf Club
- Boschendal Wine Estate
- Rust en Vrede Wine Estate
- Tokara Wine Estate
- Babylonstoren Wine Estate
- Haute Cabrière - the home of Pierre Jourdan
- Delaire Graff Estate
- Hermanus Beach Club
- ATKV Goudini Spa
- Waterford Wine Estate
- La Motte Wine Farm & Restaurant
- Kolkol Mountain Lodge
- Stark-Condé Wines
- De Hollandsche Molen
- Greenways Golf Estate




