
Holiday rentals 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 – 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

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. .

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

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.

Mountain & Sea Cottage
A neat comfortable flat in a peaceful neighbourhood, a 500m walk away from the Onrus to Sandbaai coastal path. Great locations for swimming, surfing, diving or just catching some sun rays. If you like mountain biking or hiking the mountains are also just around the corner. The stoep features a wood fired hot tub and fire pit and looks towards the mountains and a stand of bluegums which attracts a lot of bird life. The flat is on our property but is completely separate with secure parking.

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

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

The Otters Oarsman / Stanford Riverside Retreat

Berseba Rosemary Hut

FARMHOUSE @ Porcupine Hills Guest Farm

Eden Annex, off-grid, wi-fi, pool, views

Ocean Retreat, Romansbaai Beach & Fynbos Estate

Rivergate | Stable Cottage

Seaview Container Studio

Hemels in Hermanus (sleeps 4, on request sleeps 6)
When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 49 | € 47 | € 47 | € 49 | € 51 | € 48 | € 49 | € 49 | € 56 | € 47 | € 46 | € 47 |
| 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 € 9 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 & child-friendly amenities

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
70 of Caledon holiday rentals include wifi 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
Destinations to explore
- Cape Town Holiday rentals
- Plettenberg Bay Holiday rentals
- Hermanus Holiday rentals
- Langebaan Holiday rentals
- Stellenbosch Holiday rentals
- Knysna Holiday rentals
- Franschhoek Holiday rentals
- Southern Suburbs Holiday rentals
- Mossel Bay Holiday rentals
- Betty's Bay Holiday rentals
- George Holiday rentals
- Breerivier Holiday rentals
- Babylonstoren
- Erinvale Estate Hotel and Spa
- Jonkershoek Nature Reserve
- Waterkloof Wine Tasting Lounge
- Grotto Beach (Blue Flag)
- Idiom Restaurant & Idiom Wine Tasting Centre
- Fernkloof Nature Reserve
- Voëlklip Beach
- Worcester Golf Club
- Cavalli Estate
- De Zalze Golf Club
- Bugz Family Playpark
- Klein-Drakensteinberge
- Paserene Wine Farm & Wine Tasting in Franschhoek
- Arabella Golf Club
- Agulhas National Park
- Grotto Beach
- Haut Espoir
- Die Plat
- Die Gruis
- Tokara Wine Estate
- Druk-My-Niet Wine Estate
- Nederburg Wines
- Vergenoegd Löw The Wine Estate




