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Holiday rentals in Wellington

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Top-rated holiday rentals in Wellington

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

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Top guest favourite
A charming white cottage is set against a clear blue sky, surrounded by greenery. Wooden windows and a pergola enhance the rustic design. A fence encloses the property, providing an inviting space for outdoor enjoyment.
Cottage in Wellington
4.96 out of 5 average rating, 136 reviews

Olifantskop Cottage - Cosy Farm Stay

Enjoy the best of the Cape Winelands in this cosy 2 bedroom (4 people) farm cottage. Situated between two big dams, the cottage offers beautiful views stretching as far as Table Mountain on a sunny day. We allow catch-and-release Bass fishing and you are welcome to take a stroll around the farm to see the cows and many calves that roams next to the dams. The farm is 75 km from Cape Town International Airport and 6 km outside Wellington - the closest town. We'd love to host you on our farm!

Top guest favourite
The bedroom is illuminated by natural light, featuring a spacious bed with light linens. A wooden beam ceiling adds character, while large windows provide views to the outside. A door leads to an en-suite bathroom, complementing the simple yet stylish décor.
Guest suite in Courtrai
4.96 out of 5 average rating, 199 reviews

Stylishly renovated cottage

Our free standing stylishly renovated cottage is situated at the back of the property and has it’s own private garden courtyard. Fully equipped modern kitchen, living room, bedroom with skylight, Q-XL bed & en-suite bathroom. The cottage has AC, Wifi, smart TV (Netflix, Prime vid), an alarm and 24 hr patrol vehicle in this beautifull, quiet street of the neighbourhood. We are a young, lively family of 4 and some related sounds might be heard. Easy access to mountain for runs, walks, mtb.

Guest favourite
Aerial view of a log cabin with a thatched roof and a rondavel, surrounded by lush fynbos and breathtaking mountain landscapes. The gravel road is visible leading to the property, set in a tranquil countryside environment with expansive views of the surrounding hills.
Cabin in Wellington
4.95 out of 5 average rating, 73 reviews

Exclusive Mountain Retreat

Situated on foot of Bainskloof Pass in Wellington, away from everything and surrounded by pristine fynbos nature, this Logcabin with a Rondavel offers true countryside feeling with a fantastic view and complete privacy. A luxurious escape into Cape Winelands, an hour drive from the city of Cape Town. This property has its own power supply and is protected by an electric fence (no baboons). A gravel road leads up, which doesn't require a 4x4 or SUV only good ground clearance of the vehicle.

Top guest favourite
A bright living space features a large window allowing natural light to fill the room. Two comfortable chairs with intricate designs and a leather sofa are arranged around a central coffee table. A modern refrigerator is visible in the background, complementing the homey atmosphere.
Flat in Milnerton
4.9 out of 5 average rating, 48 reviews

Life is Beautiful

La Vita e Bella is a Modern self catering apartment, located in a safe neighbourhood for two persons to share and it has a separate entrance with a private braai area and access to the swimming pool. The apartment is connected to the main house’ solar system which ensures that the lights, tv and wifi stay on during load-shedding. It is well equipped, including gas/electric stove, air-fryer, microwave oven, coffee machine, kettle, toaster, airconditioning, washing machine and dryer.

Top guest favourite
A secluded cottage features a stone base with white columns and a dark metal roof. Vines grow over the front porch, which includes two chairs and small tables. Lush green grass surrounds the entrance, enhancing the natural surroundings of vineyards and mountains.
Cottage in Wellington
4.97 out of 5 average rating, 212 reviews

Vineyard Cottage at Bosman Wines

Secluded cottage surrounded by vineyards and mountains with romantic, farm-style décor, open-plan kitchen, vineyard-covered front and back porch overlooking the beautiful Wellington wine valley. Fresh white linen bedding, private bathroom and a room with a view of the vineyards and the nursery vines. Small splash pool (cold water) in the backyard, private garage for parking, wine cellar on the farm, we include a complimentary wine tasting. Home to world renowned mountain bike trails.

Top guest favourite
A rustic exterior view of a cottage features large wooden sliding doors surrounded by vibrant greenery. A stone path leads to the entrance, with well-maintained flower beds flanking the sides, complemented by a modern roof and solar panels overhead.
Cottage in Cape Winelands District Municipality
4.99 out of 5 average rating, 115 reviews

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.

Top guest favourite
A spacious garden features well-maintained grass and tall trees casting gentle shadows. The cottage is situated in the background, framed by vibrant greenery and distant mountains, creating a serene outdoor setting ideal for relaxation.
Flat in Wellington
5 out of 5 average rating, 14 reviews

Tranquil garden cottage - Acorn cottage

A stunning garden cottage located on a small holding just outside the small town of Wellington. Surrounded by vineyards and mountain views, this cottage is an ideal place to relax. Located close to but separate from the family home the cottage is completely private, has its own small plunge pool, a large garden to relax in and a deck overlooking a small dam. Fully equipped for self catering with a kitchenette. Very romantic and beautifully decorated

Top guest favourite
A serene outdoor space features a sparkling pool surrounded by lush greenery. Sun loungers are positioned beside the water, while trees provide natural shade. The home is visible in the background, blending harmoniously with the tranquil garden setting.
Guest suite in Milnerton
4.98 out of 5 average rating, 100 reviews

Beautiful country house set in lush garden

This stylish home located near the Wellington town center, schools, Huguenot College and CPUT, is hosted by Antoinette. It's the ideal spot for professional long stays, parents of students, wedding guests or explorers of the winelands looking for accommodation in the beautiful country town of Wellington, South Africa. [This property do have a back-up power system, therefor guests won't experience any loadshedding.]

Top guest favourite
A cozy sitting area is furnished with a woven chair and a matching side chair. A wooden table is positioned between them, topped with a small floral arrangement and candles. Soft light filters through a frosted window in the corner.
Flat in Milnerton
4.95 out of 5 average rating, 37 reviews

La Rose Quartier

La Rose Quartier offers a French-inspired retreat, blending beauty and comfort in every detail. With soft pastel tones and floral accents, this cozy space is perfect for couples or solo travelers seeking relaxation. Enjoy coffee on the terrace or unwind after a day of exploring. Located near wine farms and wedding venues, La Rose Quartier provides a peaceful escape with easy access to local attractions.

Guest favourite
A comfortable sleeping area features a spacious bed with soothing blue linens and decorative pillows. Two bedside tables, each with a lamp, offer soft illumination. A minimalist artwork of mountains adorns the wall above the bed, while a folding clothes rack is positioned to the side.
Flat in Milnerton
4.93 out of 5 average rating, 27 reviews

Queens Haven

Queens Haven, situated in Wellington the Heart of the Cape Winelands, is everything you need and more! With astonishing views and the excitement of Cape Town and its surroundings at your finger tips, you don’t want to miss out! Whether it’s for business or pleasure. Enjoy some Wine or Vineyards in the nearby towns which are only a short drive away! Queens Haven, where excitement and comfort awaits…

Top guest favourite
The cottage features a modern design with a sturdy grey exterior and a sloped roof. A covered porch with comfortable seating invites relaxation. Lush green grass surrounds the structure, complemented by neatly trimmed bushes. A warm sunset casts a gentle glow over the setting.
Farm stay in Stellenbosch
4.97 out of 5 average rating, 436 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.

Guest favourite
An outdoor space featuring a concrete bathing tub with steps leading up to it, positioned beneath a slatted roof. The entrance to the cottage is framed by open double doors, revealing a welcoming interior. Simple decor elements are visible, including a small table and a decorative wall piece.
Flat in Wellington
5 out of 5 average rating, 12 reviews

Naby Owl Cottage 2

Our charming Owl cottage, offers an intimate retreat for up to two guests. But can also convert into a two bedroom space suitable for friends traveling together, the space is designed with comfort and tranquility in mind, featuring an en-suite bathroom and a outdoor tub with hot water and candle-light where you can unwind while soaking in the breathtaking views of the surrounding mountains.

Popular amenities for Wellington holiday rentals

When is the best time to visit Wellington?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$98 SGD$102 SGD$107 SGD$103 SGD$104 SGD$105 SGD$109 SGD$103 SGD$108 SGD$74 SGD$94 SGD$104 SGD
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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Wellington?

    Four-legged friends are welcome in Wellington. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do guesthouse rentals in Wellington have free parking?

    Absolutely! We offer over 10 guesthouse rentals with free parking in Wellington. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Wellington?

    Wellington has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Wellington?

    Experience the best of Wellington 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.

  • What are the most popular amenities for Bed And Breakfast Rentals in Wellington?

    Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Where should I stay in Wellington?

    Make yourself at home in Wellington by choosing from our most frequently booked neighborhoods. We have over 310 vacation rentals in Wellington, and over 310 vacation rentals in Wellington.

  • Do apartment rentals in Wellington have wifi?

    Absolutely! We offer over 20 apartment rentals with wifi in Wellington. Enjoy a tailored experience with all the comforts you desire.

  • Are there Wellington vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 80 vacation homes with pools in Wellington, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Wellington have a kitchen?

    Absolutely! We offer over 20 apartment rentals with a kitchen in Wellington. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Wellington have air conditioning?

    Absolutely! We offer over 20 apartment rentals with air conditioning in Wellington. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Wellington

  • Total holiday rentals

    Explore 130 holiday rentals in Wellington

  • Nightly prices starting at

    Wellington holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,720 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    110 of Wellington holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wellington rentals

  • 4.8 Average rating

    Wellington stays are highly rated by guests – averaging 4.8 out of 5!