Holiday rentals in Upper Plain

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Upper Plain

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

%{current} / %{total}1 / 1
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.
Guest house in Western Lake
4.99 out of 5 average rating, 223 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. Same day check in may be available. ** not suitable for children or pets **

Top guest favourite
The exterior of the guest unit is visible, featuring a sleek, modern design with large glass sliding doors. A gravel pathway leads to the entrance, surrounded by minimal landscaping. The background showcases sprawling views of the Wairarapa countryside under a partly cloudy sky.
Guest house in Masterton
4.99 out of 5 average rating, 145 reviews

Self contained with spectacular views

This newly built self contained guest unit has uninterrupted beautiful views from the bedroom and private outside space. Located near Masterton hospital and golf club, you can be at Castlepoint, Riversdale, or Greytown and Martinborough for beaches, vineyards, tramping or boutique shopping within 20-45 minutes. Ideal for a couple or solo traveller there is a private outside BBQ and patio space, wifi and car parking on site. The unit is a 4km paved walk to The Queen Elizabeth Park and CBD

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, 458 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 bright living area features a comfortable couch, a dining table with chairs, and a flat-screen television on the wall. Natural light floods in through multiple windows, casting shadows on the dark carpet. Artwork is displayed on the white walls, adding character to the space.
Guest house in Masterton
4.96 out of 5 average rating, 103 reviews

Cottage nestled in estate

A fully self contained, 2 bedroom newly renovated cottage set amongst the grounds of an original 1900’s homestead with established gardens and equestrian facilities. For comfort, the cottage has air-conditioning & heating with master bedroom fitted with a ceiling fan. Underfloor heating in the bathroom and a washing machine and dishwasher in the kitchen, Weber BBQ, Nespresso coffee machine and Starlink wifi making your stay easy and comfortable. Equine facilities are available $20/day/horse.

Top guest favourite
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
4.98 out of 5 average rating, 242 reviews

​5 o'clock Somewhere: Private High-End Woodland

Awesome | Woodland Retreat ​Architectural quiet on a private hectare of mature forest, 7 minutes from Masterton. A high-spec, contemporary escape designed for seclusion and all-season comfort. ​The Space: Clean, minimalist interiors with three bedrooms and two bathrooms (master ensuite). Light-filled rooms and curated design. ​The Experience: Terraced gardens that change with the seasons. Spend evenings in the spa pool under the Wairarapa Dark Sky or by the outdoor fire with a local vintage.

Guest favourite
A charming 1920s cottage is shown with a light green exterior, surrounded by various shrubbery and trees. Flowering plants frame the entrance, which has a dark door and window accents. A wooden fence is visible, providing a clear boundary for the front yard.
Home in Masterton
4.92 out of 5 average rating, 146 reviews

Cosy cottage retreat

A 1920's cottage, that is light and warm with plenty of sunny spots, especially on the back porch. Open plan, with easy indoor/outdoor flow. Private and restful. You will love its cosy homeliness and be able to relax in its beautiful setting. With unfenced section it is unsuitable for a family with under two year olds. Easy walking distance to small supermarket, cafe, fish and chip shop and other Essentials. Two playgrounds around the corner. Or stay home with books, puzzles, games.

Top guest favourite
A path lined with grapevines stretches towards a distant cottage, set against a clear blue sky. The vibrant greenery of the vines contrasts with the well-maintained grass, inviting exploration of the vineyard's serene landscape.
Tiny home in Masterton
4.9 out of 5 average rating, 107 reviews

In The Vines

Gaze at the stars in the ink- black, Wairarapa night sky. Cottage style tiny home among vines with views towards the Tararuas. Warm, with a comfy Queen bed giving wonderful views from a sky-light. Fridge, gas cooker and basics in the handy kitchen, and a hot shower for after a day outside. A covered deck with panoramic views, and an outdoor brazier with bean bags make this a great out of town stay. 10 minutes from Masterton cafes and restaurants and well placed for exploring wine country.

Top guest favourite
The lounge area features a mix of seating options, including a white couch adorned with colorful cushions and two accent chairs. A vibrant area rug lies on the carpeted floor, and large windows allow natural light to fill the space, complemented by soft drapes.
Cottage in Masterton
4.96 out of 5 average rating, 324 reviews

Walnut Cottage, a rural idyll

Relax 10 minutes from town in a charming country cottage with all mod cons. Close enough to amenities to explore town but quiet enough to see and hear the tui's, kereru and Ruru (morepork owls) at night. There is a creek running through the bottom paddock for kids to splash in or explore for eels while you enjoy the sun on the patio. It is a great spot for a romantic getaway or a family break in the country. There are lots of walks around, animals to see and the tranquility is unbeatable.

Top guest favourite
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.
Guest house in Carterton
4.98 out of 5 average rating, 190 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 favourite
A luxury tiny house is visible, surrounded by lush gardens and farmland. The structure features wooden siding and large windows. A spacious outdoor deck enhances the view of the green lawn and trees, while native plants add a natural touch to the landscape.
Tiny home in Masterton
4.94 out of 5 average rating, 139 reviews

Halford Hideaway

This is a luxury self contained Tiny house. Nestled on the edge of a pond surrounded by expansive gardens and farmland. There are some small walking tracks to take you around the QE ll Trust wetland and ponds, and for those that are a little more energetic a walk to the top of the hill can provide you with stunning views. Perfect place to unwind, relax and enjoy an outdoor wood fire bath over looking the pond! Unfortunately cell ph reception can be patchy at the Tiny house.

Guest favourite
A black wood-burning stove is featured, with flames visible through the glass front, providing warmth and ambiance. A woven basket filled with logs is positioned alongside, and the stove is set against a light-colored wall, enhancing the cozy atmosphere.
Cottage in Upper Plain
4.92 out of 5 average rating, 345 reviews

Autumn is here, winter is coming

Modern settler cottage on historic Wairarapa property. Hosted by Brigid and Richard. Sleeps up to 8, DIY breakfast. Well-equipped kitchen. Continuous hot water. Starlink Wifi (100mbs), gas barbie, spa pool, brazier pit, trampoline, swimming pool, Smart TV, boules, board games, small book/DVD collection. Wander the 40-acre estate - native and exotic trees, orchard, lawns and paddocks. 7 minutes to Masterton by car. EV charger on site. Quiet cottage in garden setting.

Top guest favourite
The Tree House is nestled among tall trees, surrounded by vibrant purple flowers in full bloom. The wooden structure is elevated on a hillside, partially obscured by the greenery, creating a serene and secluded atmosphere.
Treehouse in Carterton
4.99 out of 5 average rating, 325 reviews

Surrounded by Nature

The Tree House is a perfect, off-the-grid retreat for nature lovers, where you can listen to birdsong, see the sunrise from the deck and hear the river flowing in the valley. Two minutes walk and you come to The Watermill Bakery serving delicious pizza on Friday evenings. The Tree House is close to a small productive lavender farm, Lavender magic, who sell cut flowers in season, and Mount Holdsworth, where you will be able to access a wide variety of walking tracks.

Popular amenities for Upper Plain holiday rentals

  1. Airbnb
  2. New Zealand
  3. Wellington
  4. Masterton
  5. Upper Plain