Family-friendly holiday rentals in South Wairarapa District

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Top-rated family-friendly rentals in South Wairarapa District

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
The exterior of a standalone suite is visible, featuring a warm red tiled roof and light-colored walls. French doors invite natural light, surrounded by potted plants on a paved surface. A small side door leads to a private entrance, framed by a white picket fence.
Guest suite in Upper Hutt
4.94 out of 5 average rating, 380 reviews

Chatsworth Retreat

Nestled amongst native trees in iconic Chatsworth Road, this accommodation provides privacy in a standalone location. Located next to our home, this is a separate suite and bathroom which has TV, bar fridge, some kitchenette amenities and a heater. Great overnight location after work commitments, a family occasion or for a weekend away. This is a very quiet location with a short drive or ten-minute walk to Silverstream Village, Supermarket, Railway Station, restaurants and a local Gastro pub.

Top guest favourite
A rustic wooden table is set with two glasses of red wine and a bottle, accompanied by a freshly baked cake on a cutting board. The background showcases a verdant landscape, with hills and trees partially shrouded in mist, creating a serene outdoor scene.
Cottage in Carterton
4.94 out of 5 average rating, 435 reviews

Provence French Cottage - a Wairarapa retreat.

Wonderful eco-sustainable French style cottage built of stone and native timber with picturesque views of the river valley and mountains. Near to Carterton, Greytown and Masterton. Drink pure artesian spring water while listening to abundant birds and sitting on your veranda. Go for a bush walk in the National Park across the river, go biking, play golf - or visit the vineyards and restaurants for a vibrant time. This is an adventure escape that is close to the vibrant Wairarapa 'good life'!

Guest favourite
Train in Upper Hutt
4.87 out of 5 average rating, 398 reviews

Tiny House Train-Eco stay

Thank you for renting the train as this really helps me. The train runs on solar power, all your water is spring water and is a great example of up cycling and recycling. The tiny house train is located on a 10 acre/4.2 hectare organic blueberry farm and was restored in 2018 and turned into a tiny house in May 2019. There is a cozy log burner plus electric blanket and heat pumps. There is a smart TV Netflix supplied . Wifi is Starlink with laptop friendly kitchen table. Self checkin after 2pm.

Top guest favourite
The exterior of the guest unit is visible, featuring a sleek, modern design with large glass sliding doors. A gravel pathway leads to the entrance, surrounded by minimal landscaping. The background showcases sprawling views of the Wairarapa countryside under a partly cloudy sky.
Guest house in Masterton
4.98 out of 5 average rating, 113 reviews

Self contained with spectacular views

This newly built self contained guest unit has uninterrupted beautiful views from the bedroom and private outside space. Located near Masterton golf club, you can be at Mt Bruce, Castlepoint, Riversdale, or Greytown and Martinborough for beaches, vineyards, tramping or boutique shopping within 20-45 minutes. Ideal for a couple or solo traveller there is a private outside BBQ and patio space, wifi and car parking on site. The unit is a 4km paved walk to The Queen Elizabeth Park and CBD

Top guest favourite
The exterior of a spacious retreat features a black-paneled structure with large windows. A well-kept lawn surrounds the area, complemented by seating arrangements and a barbecue station under the shade of lush trees, offering a serene outdoor living space.
Barn in Waihakeke
5 out of 5 average rating, 240 reviews

The Good End of the Shed.

A world away from the world -Just 5 mins from Greytown. Situated on a small organic farm in a beautiful garden. Super comfy bed, stylish, mid century decor. Wake up to birdsong, star-gaze from the outside bath while listening to the call of the ruru. Loll by the pool or borrow the bikes to go exploring. Free breakfast of good coffee, homemade muesli & fruit, artisan bread and spreads. Free-range eggs & bacon available for you to cook for $20 pp. Drive on parking, heat pump, wifi & tv.

Top guest favourite
A cozy window seat is surrounded by soft cushions and paired with a round table adorned with flowers. Sunlight filters through the large windows, offering views of green paddocks and a wooden fence in the distance, creating a serene and inviting dining nook.
Cottage in Martinborough
4.93 out of 5 average rating, 145 reviews

The Gatehouse - vintage cottage with rural views

Relax on the window seat with views over farmland in this charming vintage cottage. The deck is a sunny peaceful spot for morning coffee and, at night, for taking in the stars of the internationally renowned Wairarapa Dark Sky. The plumpy fireside sofa is perfect for sinking into with a glass of wine. The Gatehouse is only six minutes drive from Martinborough and 11 minutes to Greytown. It has two bedrooms with queen beds, a kitchen/dining space and bathroom with high pressure shower.

Top guest favourite
An outdoor dining area features a wooden table surrounded by chairs, with a warm fire burning in a modern fireplace nearby. The exterior of the home showcases two sets of glass doors, offering a view into the interior, against a backdrop of a colorful sunset.
Home in Masterton
4.97 out of 5 average rating, 223 reviews

#1 Guest Pick - 5 o’clock Somewhere

Contemporary and modern escape on 1 ha of gorgeous woodland, located just 7 mins from Masterton. Fully air-conditioned, this hidden gem has 3 spacious bedrooms 2 bathrooms, (master ensuite). Step outside to the terraced gardens bursting with colour - grab a cold one and lounge in the sun. Enjoy the spa pool under the stars or gather around the outdoor fire. Perfect for families, friends, or a quiet weekend away! 🍻 Book now, rarely available, this stunning spot is just for you.

Top guest favourite
The cottage features a light-colored exterior, with large windows allowing ample natural light. A welcoming outdoor deck is framed by low shrubs, leading to a gravel pathway. The peaceful vineyard setting is visible in the background, enhancing the serene environment.
Cottage in Dyerville
4.99 out of 5 average rating, 229 reviews

Hamden Estate Cottage

Enjoy a stay on our Martinborough vineyard. The cottage is nestled amongst the vines and offers a peaceful retreat from the city. We are 8 kilometres from the centre of Martinborough heading south on the way to Lake Ferry. You can enjoy a leisurely wine tasting at our cellar door with David who is always happy to talk wine. We will also transport you to Martinborough so that you can spend the day investigating local wineries or dine at one of the town's fine restaurants.

Top guest favourite
A modern guesthouse exterior features a spacious deck with outdoor seating, overlooking rolling green hills and a clear blue sky. The surrounding landscape includes well-maintained grass and planting, providing a tranquil rural setting.
Guest suite in Moonshine Valley
4.99 out of 5 average rating, 269 reviews

Modern rural living

Described by a former guest as "a premium destination for those seeking beauty, comfort & a flawless experience" come see it for yourself. Situated high in the hills, kick back & relax in this calm, stylish space. Experience the isolation of rural living, but with the knowledge you are only 20-30 minutes from Porirua City, Hutt Valley & Wellington City. Built in 2021, the guesthouse has all the modern amenities you need including it's own carpark, lounge, kitchen & bathroom.

Top guest favourite
A compact cabin is set against a captivating night sky filled with stars, including the Milky Way. The cabin features large windows that reflect the celestial view. A grassy area surrounds it, adding to the peaceful ambiance of the surroundings.
Guest house in Featherston
4.97 out of 5 average rating, 554 reviews

Cosy Cabin ~outdoor bath~stars~donkeys

Our self-contained, double-glazed, fully insulated compact cabin is well appointed. It stands alone on our 3 acre lifestyle property, private from our house with fabulous views to the Remutakas. There is an outdoor dining area with a BBQ. Relax in the ~outdoor bath~ under the stars in front of the wee fire (kindling & wood supplied). We have a small dog (Lucy), sweet Huntaway (Ruby), donkeys (Phoebe, Anna & Lily) & August (cat). All very friendly.

Guest favourite
An open-plan studio features a spacious bed with a soft green throw, complemented by a cozy couch. A kitchenette with appliances is visible alongside a dining table for two. Natural light fills the room through glass doors, leading to an outdoor area.
Guest house in Upper Hutt
4.82 out of 5 average rating, 179 reviews

Tucked away in Trentham

A lovely open plan studio with Queen bed, couch, dining table, smart tv and kitchenette area. Surrounded by native and succulent gardens. Modern ensuite-style bathroom, with shower. Kitchenette includes a fridge, microwave, toaster and kettle. The cabinets contain plates, bowls, cups and cutlery, sharp knives and chopping boards. Milk, drinking water, teas, coffee and sugar provided. One dedicated off-street car park by the bnb entrance.

Top guest favourite
Guest house in Waingawa
4.95 out of 5 average rating, 175 reviews

Let the countryside recharge your soul

A little slice of country just 5 minutes from Masterton. A cosy cottage with rural views across to the Tararua ranges. Sit on the patio and enjoy the dark sky views. Perfect weekend escape to enjoy all that the Wairarapa has to offer. A short drive to the Star Safari observatory, Mount Holdsworth, Carterton, Greytown and half an hour to Martinborough's wineries. If you are travelling for work, we are only a minute off the main highway.

Popular amenities for South Wairarapa District family-friendly rentals