Holiday rentals in Wellington

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Wellington

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

1 of 1 pages1 / 1
Top guest favourite
An open-plan living area features wooden beams and brick walls, with a spacious dining table surrounded by upholstered chairs. Natural light floods the space through large windows, highlighting the relaxed atmosphere. A staircase leads to a loft area, and a view of the pool can be seen outside.
Home in Franschhoek
4.92 out of 5 average rating, 156 reviews

Nooks Pied-a-Terre | Architecturally Stunning Home

Our stunning home is a 5 min walk into the village and its award winning restaurants, shops and galleries. Black Elephant, Chamonix, Dieu Donne winery's and the famous Winetram are just a short walk away. Nooks is sumptuous, private, cosy, relaxing, full of original art, high ceilings, log fires, beautiful generous spaces and mountain views. Nooks comes alive at night and is great for couples, solo adventurers, who want to be near the soul of this beautiful village. We take up to 4 adults max.

Top guest favourite
A spacious deck features a wood-fired hot tub surrounded by wooden planters, complemented by comfortable outdoor chairs. Lush greenery fills the background, enhancing the tranquil setting. Sunlight illuminates the area, creating a warm atmosphere for relaxation.
Farm stay in Stellenbosch
5 out of 5 average rating, 258 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.

Guest favourite
A sweeping view of the Hawequa Mountains is visible in the background, characterized by rugged peaks and lush greenery. The well-positioned accommodation features a spacious deck, while the surrounding landscape displays a blend of trees and natural terrain, providing a direct connection to nature.
Flat in Wellington
4.88 out of 5 average rating, 123 reviews

Heuwels

Feast your eyes on the stunning mountain scenery and fill your senses with nature's beauty, smells and sounds in a home away from home. The self-catering unit is conveniently located for outdoor enthusiasts as it's surrounded by both mountain biking/hiking routes, wine farms and great local restaurants. An absolute paradise for birdwatchers. Also, an ideal breakaway far enough from city noises yet close enough to popular amenities. The unit also has its own lush green lawn to enjoy a picnic.

Top guest favourite
A spacious balcony features two modern lounge chairs facing a panoramic view of the Hout Bay Valley and Helderberg mountains. The area is enclosed by a sleek railing, and the sliding glass doors provide seamless access to the interior space.
Flat in Hout Bay
4.93 out of 5 average rating, 441 reviews

Endless Views & Privacy

Our studio apartment opens up onto a 40sq meter balcony with a panoramic view of the Hout Bay Valley and the Helderberg mountains beyond. Large sliding doors disappear into the walls creating an unimpeded indoor/outdoor flow while the elevated position protects your privacy. The open plan bathroom faces onto an enclosed secret garden which includes a frame-less glass shower. The unit has a fully equipped kitchenette and is serviced daily except weekends and public holidays.

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, 152 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 modern guest apartment is set amidst lush greenery and gravel pathways. The structure features a light exterior and a sloped roof, with large windows and a balcony that provides views of the surrounding vineyards and farmland.
Flat in Stellenbosch
4.99 out of 5 average rating, 270 reviews

Apartment on Windon vineyard,Stellenbosch

A beautiful open plan guest apartment in the Winelands.It has magnificent views ,is beautifully furnished and is quiet and peaceful.There is a kitchenette( microwave,no oven)en suite bathroom( shower only)dining area and balcony.It’s airy & light.Guests are able to walk on the farm to stretch their legs and take in the beautiful views and fresh air or watch the zebras,springbok and wildebeest in the game camp. It is Located 7 km from the town center of Stellenbosch

Top guest favourite
A quaint cottage is enveloped by lush vines, with a welcoming front porch featuring two chairs. The roof is made of metal, and wooden doors and windows complement the natural surroundings. Soft light accents the stone pathway leading to the entrance.
Cottage in Wellington
4.97 out of 5 average rating, 228 reviews

Vineyard Cottage at Bosman Wines

A serene, beautifully styled cottage with layered textures, soft neutral tones, and thoughtful finishes throughout. It features a cosy lounge, a well-appointed kitchen, and a dreamy en-suite bedroom designed for restful comfort. Set on the 8th generation Bosman Family Vineyards, the cottage offers sweeping vineyard views and an authentic sense of countryside living. A scenic 10-minute walk leads to the cellar, where a complimentary tasting awaits.

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 Wellington
4.97 out of 5 average rating, 106 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
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
4.98 out of 5 average rating, 498 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
The eco cabin is set against a backdrop of mountains, featuring a modern design with large glass panels that provide views of the natural surroundings. A wooden deck extends from the structure, leading towards a landscaped area with lush greenery and scattered rocks.
Cabin in Bain`s Kloof Pass
4.96 out of 5 average rating, 130 reviews

Bainskloof Mountain Eco Retreat - Black Pearl

Welcome to the Black Pearl! Discover a special place that boasts breathtaking mountain views from every room. This beautifully appointed cabin is equipped with all the amenities you could want and is thoughtfully designed to provide all the comforts you need for a rejuvenating getaway. Escape the ordinary and immerse yourself in the serenity of this remarkable destination.

Top guest favourite
Home in Bain`s Kloof Pass
4.96 out of 5 average rating, 178 reviews

Magical Bainskloof Pass Getaway at Rocky Falls #1

Rocky Falls Cottage is an off-grid, spacious cottage offering ideal holiday accommodation. It is large enough for a family or group of friends, but it's still cosy enough for a couples getaway. Tucked away in the mountains of Bainskloof, Rocky Falls Cottage is set within a beautiful private nature reserve, offering peace, privacy, and natural surroundings.

Top guest favourite
A modern guesthouse is mirrored in the serene water of a pond, surrounded by green lawns and trees. The structure features a spacious terrace with outdoor seating, inviting relaxation and views of the clear blue sky and distant mountains.
Holiday home in Wolseley
4.98 out of 5 average rating, 152 reviews

Orchard Stay

We offer country living at its best. A self-catering guesthouse nestled between pear orchards, Orchard Stay offers you space and freedom inside and out. Comfort is a priority in this two bedroom farm house with both rooms having en-suite bathrooms and wow factor views of the orchards and Mostertshoek Mountain.

Popular amenities for Wellington holiday rentals

When is the best time to visit Wellington?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$109 SGD$115 SGD$100 SGD$101 SGD$102 SGD$103 SGD$107 SGD$101 SGD$106 SGD$96 SGD$98 SGD$106 SGD
Avg. temp22°C22°C21°C18°C15°C13°C13°C13°C15°C17°C19°C21°C

Frequently Asked Questions

  • What are the best places to stay in Wellington?

    Stays are frequently suggested around the town center, historic neighborhoods, and wine farm areas, each offering unique views and easy access to local attractions. Guesthouses and cottages are common options.

  • What are the best things to do in Wellington with kids?

    Discover family vineyards offering garden spaces, visit local nature reserves, or join interactive workshops at craft markets. Outdoor play areas and petting zoos can also be found around the town.

  • What are some of the best things to do in Wellington?

    Explore local wine estates, hike in the Limietberg Nature Reserve, and stroll the historic town center with its craft and food markets. Scenic viewpoints and heritage sites round out popular activities.

  • How is the weather in Wellington?

    Wellington has warm, dry summers around 62–81°F (17–27°C), and cooler, wetter winters with temperatures typically between 45–69°F (7–21°C). Rain is more common from late autumn through winter, so waterproof layers are helpful.

  • When is the best time to visit Wellington?

    Late spring to early autumn is often recommended for mild temperatures and sunny days, especially during harvest season at the vineyards. Winter brings cooler weather and greener landscapes.

  • What are the best places to visit in Wellington?

    Wine estates, the Wellington Museum, and scenic spots in Limietberg Nature Reserve are often recommended for visitors. The historic town center has galleries, markets, and heritage sites to explore.

  • What are some hiking trails in Wellington?

    Explore the trails in the Limietberg Nature Reserve, which has paths winding through mountain landscapes and rivers. Several routes around the Wellington area offer views, indigenous flora, and opportunities for family walks.

  • What are some family activities we can do in Wellington?

    Families enjoy nature walks in reserves, visiting local farms for fruit picking or animal encounters, and exploring community markets. Town parks and scenic picnic spots are frequently suggested for relaxed outings.

  • What are some of the best day trip ideas from Wellington?

    Popular day trips include exploring nearby wine regions, mountain nature reserves, or visiting towns known for their historic architecture and markets. Scenic drives through the countryside are often recommended.

  • Are there any pet friendly accommodations available in Wellington?

    Pet friendly accommodations are available in Wellington, with many guesthouses, cottages, and farms welcoming pets. Hosts often provide outdoor spaces and easy access to walking trails.

  • What are some local tips for visiting Wellington?

    Many visitors pack layers for the changing mountain weather and explore small, family-run wine farms for authentic tastings. Bringing sun protection and reusable water bottles is often suggested for outdoor adventures.

  • What is Wellington known for?

    Wellington is known for its wine estates, agricultural heritage, and beautiful mountain scenery. The town’s historic architecture, community markets, and locally rooted traditions are often highlighted by visitors.

  • What are the best hidden gems to explore in Wellington?

    Wellington has artisan workshops, local craft markets around the town center, and historic church sites that are often recommended. Small farm stalls and wine farms with tastings are frequently suggested by locals.

  • What are the best foods to try in Wellington?

    Wellington has locally produced cheeses, farm-style breads, and Cape Dutch-inspired dishes. Wine pairings and fresh fruit from nearby orchards are frequently suggested by residents.

  • What should I bring for a trip to Wellington?

    Bring comfortable walking shoes, layers for changing weather, sun protection such as hats and sunscreen, and a reusable water bottle for outdoor activities. A small backpack is useful for market visits and hikes.

  • What is the nightlife in Wellington like?

    Wellington has relaxed bars, wine cellars, and venues around the town center where you can enjoy live music, local flavors, and social evenings. The atmosphere is friendly and often rooted in the area's wine culture.

  • What are the most popular events or festivals in Wellington?

    Wellington hosts wine harvest festivals, community events at local markets, and seasonal celebrations tied to agriculture and regional heritage. Music performances and craft fairs are also frequently suggested.

  • Are there family friendly vacation rentals in Wellington?

    Wellington has a range of family friendly vacation rentals, including guesthouses, cottages, and homes often found near vineyards or scenic hills. Many hosts provide amenities suitable for children and larger groups.

Quick stats about holiday rentals in Wellington

  • Total holiday rentals

    Explore 140 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 2,990 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 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

    60 properties have a dedicated workspace

  • Wifi availability

    120 of Wellington holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wellington rentals

  • 4.9 Average rating

    Wellington stays are highly rated by guests – averaging 4.9 out of 5!