Family-friendly holiday rentals in Woodside

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Top-rated family-friendly rentals in Woodside

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

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Superhost
A small cottage is framed by overhanging willow branches and a lush garden. The building features light-colored siding with a patio area visible, surrounded by greenery and colorful flowers. The sky is clear, adding to the serene rural atmosphere.
Guesthouse in Greytown
4.81 out of 5 average rating, 181 reviews

The Brambles

Greytown has become a Mecca for boutique shopping and has some great restaurants & cafes. We are a 15min drive from Martinborough full of wineries & olive groves The Brambles is a lovingly restored 1800's outbuilding converted into a small cottage in a rural and peaceful setting. Great indoor outdoor flow to a private BBQ area, in the cottage kitchen there is a microwave, a Nespresso machine with some coffee pods & milk supplied, a 2 element electric hob and all the pots & pans you need to cook

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, 434 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'!

Top Guest favourite
A wooden platter is arranged with a selection of cheeses, crackers, and dried fruits, complemented by a bottle of Pinot Noir and two glasses of red wine. A cozy fire burns in the background, adding warmth to the inviting scene.
Cottage in Woodside
4.99 out of 5 average rating, 283 reviews

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.

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
Holiday home in Greytown
4.98 out of 5 average rating, 122 reviews

Cosy Greytown Retreat

Take a break and unwind in picturesque Greytown. There is something to see and do, whatever the season. Nestled in a quiet cul-de-sac, this two bedroom unit is perfect for a couple looking to enjoy some quiet time away. After a day of shopping or taking a bike ride along the rail trail come back to the log fire which makes for a perfect setting to sit back, relax, read a book or watch a favourite movie. Offering two bedrooms - one queen bed and one double bed for a comfortable stay.

Top Guest favourite
A spacious living area features a cozy leather sofa and two red armchairs, arranged around a central coffee table. Sliding glass doors open to a private outdoor space, framed by lush greenery. Soft lighting from overhead fixtures complements the inviting interior design.
Home in Greytown
4.93 out of 5 average rating, 312 reviews

A-Frame. Ideal for families and large groups.

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. Prior approval for pets is required ($20 per stay)

Top Guest favourite
A spacious bed is neatly made with white linens and a textured cream blanket. Decorative pillows in burnt orange and beige complement the neutral tones. A floral artwork is displayed above the bed, and natural light enters through a nearby window adorned with blinds.
Guest suite in Greytown
4.98 out of 5 average rating, 146 reviews

Potager B&B - Woodside - Greytown

On the edge of beautiful Greytown but within walking distance of coffee shops, restaurants and shops, we have created the perfect retreat. Our beautiful purpose built B&Bs are set in their own courtyard gardens within our potager garden. We supply breakfast museli, fruit, orange juice, milk, a loaf of local Ciabatta bread, butter, marmalade, jam, tea & coffee for you to enjoy at your leisure. There are views across the farmland to the Taurua Ranges and amazing night skies.

Superhost
A charming studio is surrounded by a private garden featuring lush greenery and blooming white flowers. A stone pathway leads to the entrance, which is shaded by overhanging branches. An outdoor seating area is visible, providing a serene retreat within the gardens.
Tiny home in Greytown
4.88 out of 5 average rating, 290 reviews

6 Wood Street Studio Greytown.

A very small studio located a minutes walk to Greytown supermarket, cafes, restaurants and boutique shopping. Steeped in early Aotearoa, NewZealand history, Greytown was one of the earliest towns in NZ to be settled. Magnificent stands of old trees, and beautiful gardens, Greytown is the character town of the Wairarapa and beyond. Within seven minutes you can be at Woodside railway station making access to Wellington easy as you can leave your vehicle for the return.

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.
Guesthouse in Featherston
4.97 out of 5 average rating, 552 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 favourite
Guesthouse in Waingawa
4.95 out of 5 average rating, 172 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.

Top Guest favourite
A heated pool is surrounded by a clean, tile deck and lush greenery, including trees and flowering shrubs. The pool area is fenced for privacy, with steps leading to the well-maintained grounds, creating an inviting outdoor space.
Guesthouse in Woodside
5 out of 5 average rating, 120 reviews

Cosy Cottage in Greytown

Escape to Pine Grove Cottage, a peaceful country retreat just 1.6km from Greytown village. Built-in 1865, this historic cottage offers a queen-sized bed, ensuite, living area, private patio, heat pump/air con, wifi, and a kitchenette (no cooking facilities). Enjoy a heated pool (Nov - April). Attached to the main house but with private access. Discover Greytown's charm and the beauty of Wairarapa. Book now for a serene getaway!

Top Guest favourite
A spacious bedroom features a patterned headboard and soft bedding. Nightstands with lamps sit on either side of the bed, and a natural fiber rug lies beneath. Warm lighting complements the neutral tones and creates a calming ambiance.
Guest suite in Greytown
4.91 out of 5 average rating, 405 reviews

Suite 22

100% ROMANCE GUARANTEE - Suite 22 is a 2 room self-contained suite in the front of a lovely Greytown villa. Ideal for couples wanting a romantic getaway or singles wanting a study break or some alone time. Privacy is assured. Large double bedroom & ensuite w/ shower. Separate living room & tiny kitchenette. Your own verandah & garden. A secluded outside clawfoot bath for soaking in the sun or under the stars.

Popular amenities for Woodside family-friendly rentals