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 wireless internet?

Absolutely! We offer over 10 bed and breakfast 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 bed and breakfast rentals on Airbnb with pools?

Yes! Dive into the perfect getaway at one of over 10 bed and breakfast rentals 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 80 vacation rentals in Bergsig, and over 80 vacation rentals in Caledon.

Vacation rentals in Caledon

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Caledon

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A modern cabin exterior is showcased, featuring large windows that invite natural light. A spacious deck with two chairs and a grill offers outdoor seating and relaxation, surrounded by lush green hills in the background.

Farm stay in Stellenbosch

4.98 out of 5 average rating, 247 reviews

Lakeside cabin with wood fired hot tub

Rosemary cottage is one of three cabins which rest on the edge of a lake in the heart of the Banhoek conservancy. It is a light filled, modern cabin with a wood fired hot tub, direct access to endless hiking and the finest mountain biking trails in the western cape. Although it is intended as a two person cabin, there is an open queen sized pod attached to the living room which can sleep 2 children or an extra guest for a small extra fee. There is an infrared sauna below the dam for you to use.

Top guest favorite

Farm stay in Stellenbosch

4.99 out of 5 average rating, 198 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.

Top guest favorite

A cozy lounge area features two wicker chairs with white cushions, framing a glass table. Large sliding glass doors provide a view of palm trees and the ocean beyond, allowing natural light to fill the space. Soft neutral tones create a serene atmosphere.

Apartment in Hermanus

4.93 out of 5 average rating, 121 reviews

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.

Guest favorite

The interior of a contemporary unit reveals large glass windows showcasing expansive views of rolling hills and farmlands. A wooden dining table is positioned near the windows, complementing a cozy wood-fired braai area. A wood-fired hot tub, framed by stone, invites relaxation.

Home in Overberg District Municipality

4.94 out of 5 average rating, 159 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 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.

Top guest favorite

A sandy beach is framed by gentle dunes, with sparse vegetation peeking through. In the background, a prominent rock formation catches the warm light of sunset, while a clear sky transitions from soft blue to subtle orange hues.

Guesthouse in Pringle Bay

5 out of 5 average rating, 129 reviews

Spectacular ocean views @ 38 on Penguin Studio

Unwind whilst taking in the spectacular 270 degree ocean and mountain views from the comfort of this luxury Pringle Bay studio. Just 100m from the rocky shoreline you will not only be awed by the views but will hear and feel the waves crashing onto the rocks. * Uncapped WiFi (works during load shedding) * King Size Bed * Flat screen TV with Netflix, AppleTV+ and YouTube * Fully equipped kitchen * Fireplace * Heated towel rail * Handheld bidet * Great coffee * Lockable Safe * Hair Dryer

Top guest favorite

A secluded garden pathway is framed by wooden fencing and lush greenery. Planters filled with various plants line the gravel path, inviting exploration. Natural textures and earthy tones create a harmonious atmosphere, enhanced by the gentle curves of the landscape.

Guest suite in Stanford

4.96 out of 5 average rating, 359 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.

Guest favorite

An outdoor area features a hexagonal hot tub surrounded by grassy space. A picnic table with benches is positioned beneath a large umbrella, while a braai area with a grill stands nearby, offering a scenic view of the surrounding landscape.

Cottage in Caledon

4.94 out of 5 average rating, 126 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 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

Guest favorite

A covered patio features comfortable seating arrangements and overlooks a splash pool, surrounded by well-maintained grass. The backdrop includes vineyards and mountains, enhancing the serene environment of the property.

Farm stay in Worcester

4.96 out of 5 average rating, 269 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.

Guest favorite

A circular fire pit is surrounded by seating, with six guests gathered around. Soft lighting from hanging bulbs creates an inviting atmosphere. Lush greenery frames the scene, offering a peaceful outdoor space for socializing in the evening.

Cottage in Greyton

4.86 out of 5 average rating, 249 reviews

Potato Patch Self Catering Cottage

This versatile thatched roofed cottage offers contemporary country comfort with a dash of history. It is one of the two cottages located on the owners property offering its own entrance and private 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. A five minute walk will get you to the village Centre.

Top guest favorite

A cottage with a spacious deck overlooks a private plunge pool, framed by well-manicured shrubs and an expansive lawn. The sky displays a gradient of colors as the sun sets, creating a peaceful atmosphere. The structure features a chimney and large windows that allow for natural light.

Farm stay in Stellenbosch

4.97 out of 5 average rating, 395 reviews

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.

Superhost

A tranquil view from the verandah features a wood-fired hot tub beside a dark, reflective surface. Two glasses are positioned nearby, with rolling green hills and distant mountains providing a scenic backdrop under a clear sky.

Farm stay in Bot River

4.79 out of 5 average rating, 285 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.

Guest favorite

A serene landscape is captured, featuring a calm pond reflecting the surrounding greenery and rolling hills. Indigenous shrubs and grasses border the water, with distant farm structures slightly visible under a clear sky. The gentle colors of nature evoke a tranquil atmosphere.

Cabin in Grabouw

4.95 out of 5 average rating, 251 reviews

Brookelands Stone Cottage

Brookelands Stone Cottage is tucked away in a magical wooded setting amid indigenous trees and shrubs in the Elgin Valley. Situated on a small working apple, pear and grape farm it has all the trappings of a romantic hideaway, but within easy access of all that the area has to offer.

Vacation rentals for every style

Get the amount of space that is right for you

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Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Caledon vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Caledon

Guest favorite

A modern bathroom features a white porcelain toilet next to a sleek, wall-mounted sink. The sink is complemented by a stylish countertop, and a contemporary mirror reflects the light from overhead fixtures. Light wood flooring contrasts with the soft-colored walls and window coverings.

Home in Caledon

4.94 out of 5 average rating, 78 reviews

The Pepper Tree

Top guest favorite

A well-equipped kitchen is displayed, featuring a gas stove with multiple burners. A view of lush greenery and distant mountains can be seen through a window, framing the serene outdoor environment. Kitchen utensils and a kettle are arranged neatly on the counter.

Home in Greyton

5 out of 5 average rating, 15 reviews

Garden Cottage

Superhost

An outdoor patio area features a wooden dining table surrounded by matching chairs, positioned under a covered roof. A stone fireplace is visible in the background, with a view of lush green fields and distant hills beyond. Natural light enhances the inviting outdoor space.

Farm stay in Caledon

4.88 out of 5 average rating, 17 reviews

The Cottage at Black Eagle

Top guest favorite

A serene landscape captures a calm body of water reflecting the clear blue sky. Lush greenery borders the water's edge, while distant mountains create a stunning backdrop against the horizon. A dirt path runs alongside the water, inviting exploration of the natural surroundings.

Guesthouse in Villiersdorp

5 out of 5 average rating, 87 reviews

Kliprivier Cottage

Guest favorite

A modern pod is positioned on a gentle slope overlooking a serene body of water. Surrounding hills frame the landscape, while patches of burnt vegetation indicate recent changes. The sky above is overcast, contributing to a calm atmosphere.

Shipping container in Villiersdorp

4.95 out of 5 average rating, 64 reviews

Exquisite panoramic one bedroom Mountain Eco Pod

Top guest favorite

A rectangular lap pool is positioned on a stone terrace, surrounded by a vast natural landscape. Two loungers are placed near the pool, and the backdrop features dramatic mountains under a clear blue sky, enhancing the tranquil setting.

Home in Greyton

4.95 out of 5 average rating, 22 reviews

Heuningkloof Eco Cottage Greyton

Guest favorite

A charming single-story home is framed by lush greenery, featuring a welcoming entrance with white steps leading to a porch. The light green exterior complements the natural surroundings, while the inviting front door is bordered by a decorative grille.

Townhouse in Caledon

4.83 out of 5 average rating, 42 reviews

De Hoekhuys: wedding guests, remote working

Top guest favorite

Townhouse in Caledon

4.96 out of 5 average rating, 54 reviews

Town and Country Self-catering Accommodation

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Quick stats about vacation rentals in Caledon

Total rentals
70 properties
Nightly prices starting at
ﺩ.ﺇ37 before taxes and fees
Total number of reviews
820 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 wireless internet?
Absolutely! We offer over 10 bed and breakfast 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 bed and breakfast rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 bed and breakfast rentals 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 80 vacation rentals in Bergsig, and over 80 vacation rentals in Caledon.

Vacation rentals in Caledon

Top-rated vacation rentals in Caledon

Vacation rentals for every style

Popular amenities for Caledon vacation rentals

Other great vacation rentals in Caledon

Quick stats about vacation rentals in Caledon

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Rentals with a pool

Rentals with dedicated workspaces

Frequently Asked Questions

Destinations to explore