
Holiday houses in Caledon
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Top-rated holiday 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

Oak & Owl Self-catering Cottage
Come see the whales and taste the wine! Romantic, self-catering cottage with quality finishes in secure estate, Onrus – 25 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

Kliprivier Cottage
Kliprivier Cottage is nestled within vineyards and surrounded by the beautiful Stettyn mountains. We are completely off-grid with solar electricity, so it's the perfect escape from the city where one can forget about load shedding and traffic for a while. We are just across the road from Stettyn Family Vineyards tasting room, where award winning wines and cheese platters can be enjoyed. We've got amazing MTB / running trials, as well as a beautiful dam to do some bass fishing and/or birding.

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

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.

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.

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 holiday rentals
Other great holiday rentals in Caledon

Berseba Rosemary Hut

FARMHOUSE @ Porcupine Hills Guest Farm

Trinity Cabin

Serenity cabin on the dam

Romantic lakeside cottage

Seaview Container Studio

Heart & Soul

Rolling Hills Farmstead 2 BR Eco-Chalet
When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $100 NZD | $96 NZD | $96 NZD | $100 NZD | $105 NZD | $98 NZD | $100 NZD | $100 NZD | $116 NZD | $96 NZD | $94 NZD | $96 NZD |
| 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 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
Destinations to explore
- Cape Town Holiday rentals
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- Franschhoek Holiday rentals
- Southern Suburbs Holiday rentals
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- Babylonstoren
- Jonkershoek Nature Reserve
- Waterkloof Wine Tasting Lounge
- Erinvale Estate Hotel and Spa
- Grotto Beach (Blue Flag)
- Idiom Restaurant & Idiom Wine Tasting Centre
- Fernkloof Nature Reserve
- Voëlklip Beach
- Worcester Golf Club
- Bugz Family Playpark
- De Zalze Golf Club
- Klein-Drakensteinberge
- Cavalli Estate
- Paserene Wine Farm & Wine Tasting in Franschhoek
- Arabella Golf Club
- Agulhas National Park
- Die Plat
- Grotto Beach
- Die Gruis
- Haut Espoir
- Vergenoegd Löw The Wine Estate
- Tokara Wine Estate
- Nederburg Wines
- Druk-My-Niet Wine Estate




