Family-friendly vacation 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 favorite

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, 368 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 favorite

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, 424 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 favorite

A bright red train exterior is visible, featuring multiple windows and doors. Outdoor seating includes wooden benches and a rectangular dining table, positioned on a paved surface. Lush greenery surrounds the area, creating a serene rural atmosphere.

Train in Upper Hutt

4.87 out of 5 average rating, 391 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 favorite

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, 238 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 favorite

The property is set in a scenic rural landscape, featuring a modern single-story house surrounded by lush greenery. Rolling hills and fields extend into the distance, under a clear blue sky. A gravel driveway leads up to the residence, enhancing the property’s inviting atmosphere.

Farm stay in Masterton

4.97 out of 5 average rating, 135 reviews

Spacious B&B suite on a lifestyle (7 acre)property

You can be as involved as you wish on this family-friendly lifestyle block property. You can feed the chooks and pigs, walk through our paddocks mingling with the pet sheep and collect fresh eggs and veggies from the garden or just relax in the tranquil setting of our "Tui Suite" and enjoy the view of the Tararua ranges and we'll let you just be. Well equiped self-contained suite - suits maximum of 2 adults and 2 children, comfortable beds and hearty breakfast provisions provided.

Top guest favorite

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

4.98 out of 5 average rating, 204 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 favorite

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, 221 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 favorite

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, 255 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.

Guest favorite

The spacious bedroom features a double bed dressed in light linens, complemented by decorative pillows and a soft throw. Modern art hangs above the bed, and a cozy armchair with patterned cushions is positioned nearby, enhancing the room's inviting atmosphere.

Guest suite in Upper Hutt

4.9 out of 5 average rating, 292 reviews

Guest Suite - Master bedroom with ensuite, 2 beds

Tidy master bedroom located downstairs from the main house. It has its own entrance, private bathroom ensuite, and outdoor seating area to enjoy the peaceful and quiet surroundings. Close to all amenities with a 2-minute drive or 10-minute walk to New World supermarket, park, railway, and bus stop. Quick and easy access to the motorway. Please note the location on the map below. We are approximately a 10-minute drive to Upper Hutt and a 30-minute drive to Wellington.

Top guest favorite

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.

Guesthouse in Featherston

4.97 out of 5 average rating, 541 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.

Top guest favorite

The exterior view of the Tui Suite is highlighted by a softly illuminated patio with two woven chairs. Large glass doors provide a glimpse into the serene interior, with views of distant mountains and a tranquil evening sky in shades of blue.

Guesthouse in Western Lake

4.99 out of 5 average rating, 189 reviews

Tui Suite at Wairarapa's Lakeview Lodge

Welcome to our luxury peaceful escape location. Just 60 minutes from Wellington, your private suite overlooks Lake Wairarapa and is surrounded by farmland, bush and lake views and includes your own private spa and gardens - a perfect place to escape, gaze at the night sky, and relax. Single nights available Sunday-Thursday, no cleaning fees, a light breakfast is included, and a kitchen and BBQ are available for self-catering.

Top guest favorite

Guesthouse in Waingawa

4.94 out of 5 average rating, 153 reviews

Let the countryside recharge your soul

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