Holiday houses in Woodside

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Top-rated holiday rentals in Woodside

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The cottage is framed by a lush garden, featuring seating areas and a picnic table on a grassy lawn. A separate Annexe with a blue roof is visible to the left. Mature trees and colorful flowers enhance the tranquil outdoor setting.
Cottage in Greytown
4.99 out of 5 average rating, 111 reviews

Bumblebee Cottage Greytown

We had this cottage purpose built 20 years ago and have furnished and appointed it with love and care. One queen bedroom, one king single bedroom and Annexe 3 m away with double bed, electricity and linking deck to Bumblebee. Town water, gas water heating, in a large tree-clad garden, you have privacy + space + parking. New heatpump. Water feature. GHD! Electric blankets. Unsuitable for children under 3. Dogs must be on leash outside as we are rural. No cleaning fees. All linen supplied.

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
4.95 out of 5 average rating, 455 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, 287 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
An outdoor dining area features a wooden table surrounded by chairs, with a warm fire burning in a modern fireplace nearby. The exterior of the home showcases two sets of glass doors, offering a view into the interior, against a backdrop of a colorful sunset.
Home in Masterton
4.97 out of 5 average rating, 239 reviews

#1 Guest Pick - 5 o’clock Somewhere

5 o’clock Somewhere is a modern, contemporary escape on 1 hectare of gorgeous mature deciduous woodland, located only 7 mins from Masterton. Fully air-conditioned, this hidden gem has 3 spacious bedrooms with 2 bathrooms, (the master is ensuite). Step outside to the mature terraced gardens are bursting with colour - grab a cold one and lounge in the sun or enjoy the spa pool under the stars and gather around the outdoor fire. Perfect for families, friends, or a quiet weekend away! 🍻

Guest favourite
A spacious wooden deck features an outdoor dining area with a round table and four white metal chairs. Large glass doors lead into the interior space, while lush greenery and gardens are visible in the background under a shaded canopy.
Home in Dalefield
4.83 out of 5 average rating, 226 reviews

Rose End Escape

This peaceful abode is set amongst beautiful gardens and luscious farming plains, making for the perfect spot for a break away from the city. With only a hop, skip and a jump, you are a short 5 minute drive from shopping till you drop in Greytown, and wandering the beautiful daffodil fields of Carterton. If nature is more your thing, within a few minutes drive you could also find yourself trekking the picturesque tracks of the Waiohine Gorge or visiting the vineyards of Martinborough.

Top Guest favourite
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
4.99 out of 5 average rating, 221 reviews

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 for self-catering. ** not suitable for children or pets **

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, 328 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 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, 109 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 favourite
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, 218 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.

Top Guest favourite
Yurt in Greytown
4.98 out of 5 average rating, 596 reviews

Greytown Yurts - Luxurious Glamping Experience

Greytown yurts is luxury accommodation with all the fun and appeal of glamping but with total comfort. There is a ducted heat pump to keep you comfortable all year round. The interior offers a luxurious and calming environment, with beautiful views across our garden. It has a very comfortable king size bed (183 x 203 cm), with superior linen, bedding, towels and robes. There is a one off cleaning fee added to the price.

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, 417 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.

Top Guest favourite
An outdoor bath is positioned on a wooden deck, overlooking rolling green hills under a soft sunset glow. Fresh linens are draped nearby, and a glass is placed on the edge, complementing the serene atmosphere of the expansive landscape.
Cabin in Dyerville
4.96 out of 5 average rating, 432 reviews

The Hut

The hut is a beautifully crafted off the grid cabin located located on a sheep and beef farm, Daisybank, just minutes out of Martinborough . Open the doors right up on a nice day and enjoy the fresh air or cozy up with a blanket on the couch in front of the fire when the weather makes you want to bunker down. The outdoor bath is the icing on the cake to allow you to take in the views while relaxing in the tub

Popular amenities for Woodside holiday rentals

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