Family-friendly holiday rentals in Woodside

Unbelievable Peace at Underhill Cottage B+B

You’ll love my place - the peacefulness of the setting, comfy bed and tranquility of the countryside. Wake to native birds singing. Close to parks, public swimming baths, walks & the train. 15 Minute walk from Featherston Township with its quirky shops, cafes and famous Cheese Shop. Designed for couples seeking a quiet retreat, or overseas guests seeking a touch of country life. Also caters for up to 2 additional guests using the bedsettee (additional charge applies). English + German spoken

Longforde Cottage

Welcome to Longforde, a very special, charming and beautifully furnished cottage attached to our main home but completely independent with your own access and landscaped to ensure your absolute privacy. Set on 4 acres of stunning gardens, each room has private rural views of the countryside and Tararua ranges. We are located at the end of one of Greytowns most beautiful streets, a walkable 2km into the shops and cafes. As well, we are on a popular walking and biking route to the Waiohine river.

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'!

A-Frame. Price now includes all service fees.

The house for all seasons, occasions and ages. Double glazed with new thermal curtains. Heat pump and log burner in downstairs living room and heatpump in upstairs bedroom to keep you cosy in winter and cool in summer. The grounds are spacious and private. Great for playing games, BBQ and evening drinks on the sun-drenched deck or in front of the outdoor fireplace. Toys, board games, bikes and sports equipment are provided. Fully fenced. Dog friendly - $25 per stay. Please include in booking

​5 o'clock Somewhere: Premium Wairarapa Escape

Awesome | escape ​exquisite Architecture, peaceful, completely private, woodland retreat, 7 minutes from Masterton. High-spec, contemporary home, secluded getaway with all-season comfort. ​Clean, minimalist interiors with three bedrooms and two bathrooms (master ensuite). Light-filled rooms and curated design with exquisite landscape garden views. ​Terraced gardens changing with the seasons. Lazy evenings in the spa under the Wairarapa Dark Sky by the outdoor fire with a glass of wine

The View

On a plateau overlooking the Ruamahanga river valley is our cosy two bedroom fully self contained cottage. The views are jaw dropping, backdropped by the Tararua Ranges. On the river flats below, summer crops form a patchwork of different colours. Above, the big sky can be an endless blue or filled with rolling banks of cloud and truly spectacular sunsets. At night the wondrous canopy of stars is why the region is an official International Dark Sky Reserve. It’s all utterly peaceful.

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 $25 pp. Drive on parking, heat pump, wifi & tv.

1890s Charming Country Cottage with garden

Escape to this loveable 1890s cottage on a 2.6‑hectare organic garden estate. Sleeps 6 in 3 cosy bedrooms, perfect for creative retreats, family weekends or nature lovers—yet just a short drive from town. It has a wood fire, heaters and electric blankets. The cottage is well decorated and equipped with essentials. There is one queen, one double, and two single beds, all with quality linen IMPORTANT: The double room is accessed through the single bedroom. Please note before booking.

Historic Charm - Tranquil Setting - Walk to Town

Step into the historic charm of Kowhai Cottage, nestled in Greytown's tranquil settings. A stone's throw from the main street, this 1900s cottage offers a serene escape with a sunlit garden and shady outdoor settings, cosy fire, and tasteful furnishings. Perfect for families or groups, enjoy a fully-equipped modern kitchen, laundry and air-conditioning, all within walking distance of the town's delights, and a short drive to the nearby vineyards. The picture perfect getaway!

Picture Perfect in the heart of the Greytown

From the front gate to the rear sunny garden, this beautifully appointed villa is near the heart of Greytown Village situated on the main road, perfect for couples, family and friends. A three bedroom 2 bathroom house on a private spacious fully fenced property, with on-site parking. Just a casual stroll away is Greytown's Village with its renowned cafes, restaurants, bars and boutique shopping. A roaring log-fire with all firewood supplied plus Wi-Fi and 2 smart TV's.

Gorgeous Garden Cottage

Kew Cottage Idyllic character home nestled in a much loved cottage garden. Tasteful in decor the cozy living spaces flow seamlessly to the sun-drenched garden. Enjoy al fresco dining under the grapevines or finish the day with toasted marshmallows on the outdoor open fire. Comprising two bedrooms, one bathroom two heat pumps, large utility space and much more. This home away from home is centrally located and an easy walk to central Greytown- shops cafes and bars.

Woodside Suite: peaceful semi-rural life

You’ll love our location, enjoy the peace and quiet. We are rural but with all the benefits of being within walking distance of town, just 10 minutes. We are also located on the road that leads to Woodside railway station. Our home is good for couples or travelers who are looking for a bit of rest and relaxation. We have also set up a Guidebook for some local pointers.