Vacation rentals in Woodside

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Top-rated vacation rentals in Woodside

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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

Tui Suite at Wairarapa's Lakeview Lodge

Welcome to our 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 kitchenette and covered BBQ are available. Same day check in may be available. ** not suitable for children or pets **

4.99 out of 5 average rating, 245 reviews

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

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.

4.99 out of 5 average rating, 292 reviews

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

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'!

4.95 out of 5 average rating, 474 reviews

Top guest favorite

Home in Woodside

Greytown Cottage & Cabin | Outdoor bath | Dark Sky

Nestled beneath the Tararua Ranges, opposite the Greytown Bike Trail, our new cottage & cabin (completed 2025) offers a peaceful Wairarapa escape designed with adults in mind. • Private outdoor bath • Enjoy the Wairarapa Dark Sky Reserve • Boutique shops, cafés and supermarket 2.5km away • 3 mins to Woodside Station • Just 1 hour from Wellington Enjoy a relaxing getaway or midweek work retreat. Work remotely during the day, then walk, bike, soak in the outdoor bath and enjoy Greytown’s cafés.

5.0 out of 5 average rating, 56 reviews

Top guest favorite

An open-plan living area is visible, with large glass doors revealing a serene outdoor setting at dusk. Contemporary light fixtures illuminate the space, complemented by a comfortable seating arrangement. A well-maintained garden area and wooden decking extend the interior to the tranquil surroundings.

Home in Masterton

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

4.97 out of 5 average rating, 274 reviews

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

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

4.93 out of 5 average rating, 339 reviews

Top guest favorite

An outdoor deck features a dining table surrounded by wooden chairs, shaded by a large umbrella. Rolling green fields and distant hills provide a scenic backdrop under a clear blue sky with scattered clouds.

Home in Ahiaruhe

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.

5.0 out of 5 average rating, 105 reviews

Top guest favorite

The exterior of a charming cottage with a light blue facade is shown. Two small tables with chairs are positioned on the front porch, while neatly trimmed hedges and a decorative lemon tree adorn the garden, complemented by a pathway leading to the entrance.

Cottage in Greytown

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!

4.98 out of 5 average rating, 126 reviews

Top 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

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.

4.91 out of 5 average rating, 114 reviews

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

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.

4.97 out of 5 average rating, 229 reviews

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

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.

4.91 out of 5 average rating, 434 reviews

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

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. The maximum number of guests is two.

4.97 out of 5 average rating, 206 reviews