Family-friendly vacation rentals in Woodside

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Top-rated family-friendly rentals in Woodside

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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, 418 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, 278 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

An open living area displays a green couch adjacent to a wooden coffee table. A bookshelf filled with books stands against one wall. A farmhouse-style dining table with black chairs is positioned near the kitchen, which features a window allowing natural light to enter.

Vacation home in Greytown

4.98 out of 5 average rating, 112 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 and dining area features a comfortable dark sofa with decorative pillows. A glass coffee table sits on a textured rug, accompanied by a selection of books. A dining table with chairs is visible, and large windows allow natural light to fill the space.

Guesthouse in Carterton

4.99 out of 5 average rating, 172 reviews

White shed, modern rustic

Our rural shed is a spacious self-contained getaway with sun and views of the surrounding countryside. It is best suited for 2 guests, but can accomodate 4, with a queen size bed upstairs and a fold-out sofa in the living room. A fold out bed is available for children. We stock the kitchenette with free range eggs, locally made bread, homemade jam, butter, milk, tea and coffee. There’s a BBQ available. We’re 5 minutes walk to the Carterton shops and near the railway station.

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)

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, 137 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 light blue house with a welcoming yellow door is framed by a white picket fence. The porch is adorned with a bench and features multiple windows, allowing natural light to illuminate the entrance. A tall tree is visible beside the home.

Home in Greytown

4.91 out of 5 average rating, 103 reviews

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.

Top guest favorite

A charming cottage features a rustic exterior adorned with greenery, set against a vibrant sunset sky. Warm light glows from the windows, while a gravel pathway leads to a welcoming front entrance surrounded by manicured hedges and colorful plants.

Cottage in Greytown

4.97 out of 5 average rating, 206 reviews

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.

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

4.89 out of 5 average rating, 287 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 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, 156 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 living area features a comfortable striped sofa and two floral armchairs, enhancing the cozy setting. A wooden coffee table sits in the center, complemented by a neutral rug. Light streams through multiple windows, illuminating the space and reflecting a blend of indoor and outdoor elements.

Home in Greytown

4.95 out of 5 average rating, 124 reviews

Greytown Cottage: Fixed Fiber, Sky TV, Linen.

Refurbished and fully insulated 1950's 2 Bedroom 100sqm Cottage perfectly located in central Greytown. Just a 3 minute walk from the main shops. Quality Bed Linen/Towels provided. Cleaning Fee included. HeatPump that heats cottage in minutes. Air Con for the hot summer months. Two bikes (and helmets) available for use. 6 Free Range eggs from owners pet Hens on arrival. Note: Hens not kept at property :) Table Tennis Table in garage.

Top guest favorite

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, 397 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.