Family-friendly vacation 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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Top guest favorite
A cottage exterior presents a welcoming entrance, featuring a bench beneath hanging flower baskets. Glass double doors lead into the space, with a gray concrete porch providing access. The roof is sloped, and a grassy landscape is visible in the background.
Guesthouse in Tauwharenīkau
4.94 out of 5 average rating, 160 reviews

Gorgeous country cottage - 1 bedroom

Set amongst 3.3 hectares, surrounded by farmland and completely independent from our homestead, you will find a welcoming cottage to relax and restore. Perfectly positioned between Featherston (6 minutes), Greytown (9 minutes) and Martinborough (11 minutes), you are spoilt for choice. Whether it be vineyards, cafes and boutique shops you are after or bike trails, exploring the local lakes and landscape it’s all on your doorstep. There is good 4G cell-phone coverage. Check-in is by lock-box.

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, 428 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 favorite
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, 281 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 favorite
Vacation home in Greytown
4.97 out of 5 average rating, 119 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 favorite
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, 309 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 favorite
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, 143 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.

Guest favorite
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, 288 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 favorite
The cottage exterior features a light gray facade with white decorative trim and a bright yellow door. Surrounding gardens are lush with greenery and vibrant flowers. The entrance is framed by soft foliage, creating a welcoming atmosphere in a serene outdoor setting.
Cottage in Greytown
4.97 out of 5 average rating, 197 reviews

Country Bliss : charming historic cottage

Country Bliss Cottage is an original historic Greytown cottage its origins dating back to the 1880's . The cottage still retains its original character and charm but with modern day comforts. The garden is private and sunny with an abundance of bird life, mature fruit trees and cottage garden flowers. The decor is a mixture of vintage and new with quality furnishings throughout . A roaring log-fire with all firewood supplied makes for a cosy winter retreat.

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, 545 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 bedroom features a spacious bed adorned with neutral-toned linens. A desk and chair are positioned near a window, allowing natural light. Soft grey curtains frame the window, and an open doorway leads to a cozy sitting area with floral-patterned furniture.
Guesthouse in Greytown
4.97 out of 5 average rating, 162 reviews

Boutique Greytown cottage

Nestled in the back garden of a century-old house, is a sunny, self-contained, private cottage. Two sets of french doors open into a private garden. The cottage is 3 minutes walk to the vibrant centre of Greytown with cafes and boutique shops. A continental breakfast is provided. Discounts are provided for longer stays. A small foldaway bed is available at an additional fee for one child under 12. Otherwise the maximum number of guests is two.

Top guest favorite
The front patio of the cottage features seating arrangements with white wicker furniture, surrounded by vibrant flowers. The cottage showcases classic architecture with a corrugated metal roof and decorative eaves, and the entrance is accentuated by two windows with black curtains.
Guesthouse in Woodside
5 out of 5 average rating, 119 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 cruiser bikes and 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 favorite
Guesthouse in Waingawa
4.94 out of 5 average rating, 161 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.

Popular amenities for Woodside family-friendly rentals