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Vacation rentals in Wellington

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Top-rated vacation 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, 135 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!

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
4.94 out of 5 average rating, 70 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. A luxurious escape into Cape Winelands, an hour drive from the city of Cape Town. This property has its own power supply (no load shedding) 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.
Apartment in Milnerton
4.96 out of 5 average rating, 46 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, 209 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
Cottage in Paarl
4.96 out of 5 average rating, 126 reviews

Mon Repos, free standing cottage, Paarl, Cape Town

Free standing and spacious cottage on a large Heritage dwelling in the heart of old Paarl. Secured, gated, off-street private parking leads onto onto patio and garden. Renovated to a modern space with functional kitchenette, living area and en suite bathroom . The property is ideally situated within walking distance of restaurants and coffee shops. Boys and Girls High Schools are within short walking distance, (300/450m). This is an ideal base from which to explore surrounding areas.

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.
Apartment in Wellington
5 out of 5 average rating, 13 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, 99 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.
Apartment in Milnerton
4.94 out of 5 average rating, 36 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.

Top 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.
Apartment in Milnerton
4.96 out of 5 average rating, 24 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, 430 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.

Top 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.
Apartment in Wellington
5 out of 5 average rating, 11 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.

Top guest favourite
A panoramic view of the mountains surrounding the area is captured, showcasing the rugged terrain under a clear blue sky. Lush vineyards and a small town are visible at the base, highlighting the region's natural beauty and agricultural landscape.
Farm stay in Cape Winelands District Municipality
4.97 out of 5 average rating, 35 reviews

Hexberg se Kop

Enjoy your stay at this secluded two bedroom house on a working wine farm. This property offers uninterrupted views of the Hawekwa, Paarl, Paardeberg and Kasteelberg mountains. Whether you chose to spend your time sipping wine on one of the several adjacent farms or exploring Wellingtons world class hiking and cycling trails, Hexberg se Kop will not disappoint.

Popular amenities for Wellington vacation rentals

Quick stats about vacation rentals in Wellington

  • Total rentals

    130 properties

  • Nightly prices starting at

    $14 CAD before taxes and fees

  • Total number of reviews

    2.7K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    80 properties have a pool