Guesthouse holiday rentals in South Wairarapa District

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Top-rated Guesthouses in South Wairarapa District

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Guest favourite
The cottage exterior features a light-colored wood facade with a covered porch. Two sets of chairs are positioned in front of large glass doors, providing a place to relax. Surrounding greenery and flower beds enhance the outdoor space, inviting a connection with nature.
Guesthouse in Upper Hutt
4.93 out of 5 average rating, 117 reviews

'The Cottage'

‘The Cottage’, is a cosy, self-contained cottage situated in the lovely Kaitoke countryside, a 40 minute drive from Wellington; 20 from the Wairarapa and 10 from Upper Hutt. 'The Cottage', is also the perfect location for access to the Rimutaka Incline Trail and Aston Norwood Gardens & Cafe. It is a modern two-bedroomed cottage, which could accommodate up to four guests. From the lounge, you can enjoy watching the animals play in the paddock below or the birds fluttering around in the trees.

Top Guest favourite
A private outdoor area is presented, featuring a small table with two red chairs on a concrete patio. Colorful tiles decorate one wall, while a grassy area and trees provide a natural backdrop. Sunshine brightens the space, creating a welcoming atmosphere.
Guesthouse in Upper Hutt
4.94 out of 5 average rating, 139 reviews

The OverFlo

The OverFlo is a cozy, compact self-contained space with private access & courtyard, situated in the picturesque Kaitoke countryside. Refurbished to a high standard & attention to detail, it offers a peaceful, comfortable getaway, in a delightful private rural setting. Upper Hutt, Brewtown & the railway station are just 10min away & 20 min from the Wairarapa, the wine trail & the many cafes, restaurants & boutique shops. Wellington & all that this vibrant city has to offer is a 40 mins drive.

Top Guest favourite
The exterior of the house showcases a single-story structure with a light grey facade. A spacious carport is visible, providing sheltered parking. A small wooden deck extends from the front entrance, inviting access to the garden area, which features well-maintained grass and landscaping.
Guesthouse in Upper Hutt
4.98 out of 5 average rating, 156 reviews

Poets Block Haven in Upper Hutt

Enjoy our 1 bedroom house that is 5 min drive from the Upper Hutt city centre with quick access to the motorway to Wellington City. Open plan full kitchen, dining room and lounge with everything you would need to cook a meal. Separate bedroom with a new queen bed. If required a single bed can be added to the lounge to provide extra guest. Bathroom with new shower, toilet and vanity. Washing machine and dryer in the bathroom and a clothes line. Off street parking for two cars. Pet friendly.

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.
Guesthouse in Masterton
4.98 out of 5 average rating, 109 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 golf club, you can be at Mt Bruce, 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

Guest favourite
A private outdoor area features a wooden deck leading to a hot tub, surrounded by lush greenery and flowering shrubs. A small black table and chairs are positioned nearby, inviting relaxation in a serene setting.
Guesthouse in Carterton
4.9 out of 5 average rating, 247 reviews

Kererū Rest Take time amongst nature

Kererū Rest is in a semi rural position, enjoy relaxing on the deck or in the private outside beautiful bath. There is a bar fridge/freezer, toaster and kettle. Breakfast selection provided eg: muesli, bread, butter, spreads, orange juice,milk, teas and fresh plunger coffee. This may work for travellers who don't plan on spending vacation time cooking although a gas barbeque is available (see photo) Greytown is five minutes away providing boutique shopping and a variety of dining.

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.
Guesthouse in Carterton
4.99 out of 5 average rating, 177 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 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, 549 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 favourite
A modern guest house is set against a clear blue sky, framed by lush greenery. The building features large glass doors leading to a welcoming interior. A neatly maintained lawn extends in the foreground, enhancing the outdoor setting.
Guesthouse in Martinborough
4.98 out of 5 average rating, 151 reviews

Amberley Guest House

Enjoy the best of both worlds! Amberley Guest House is a modern two bedroom self contained retreat nestled on two acres on the edge of Martinborough The guest house has its own entry meaning you can be completely private and independent It offers a welcoming and comfortable lounge, dining and kitchen area with two bedrooms and a modern bathroom Sit back and relax on the large deck with comfy couches and enjoy the setting sun in peace and quiet

Guest favourite
An open-plan studio features a spacious bed with a soft green throw, complemented by a cozy couch. A kitchenette with appliances is visible alongside a dining table for two. Natural light fills the room through glass doors, leading to an outdoor area.
Guesthouse in Upper Hutt
4.81 out of 5 average rating, 177 reviews

Tucked away in Trentham

A lovely open plan studio with Queen bed, couch, dining table, smart tv and kitchenette area. Surrounded by native and succulent gardens. Modern ensuite-style bathroom, with shower. Kitchenette includes a fridge, microwave, toaster and kettle. The cabinets contain plates, bowls, cups and cutlery, sharp knives and chopping boards. Milk, drinking water, teas, coffee and sugar provided. One dedicated off-street car park by the bnb entrance.

Top Guest favourite
Guesthouse in Waingawa
4.95 out of 5 average rating, 168 reviews

Let the countryside recharge your soul

A little slice of country just 5 minutes from Masterton. A cosy cottage with rural views across to the Tararua ranges. Sit on the patio and enjoy the dark sky views. Perfect weekend escape to enjoy all that the Wairarapa has to offer. A short drive to the Star Safari observatory, Mount Holdsworth, Carterton, Greytown and half an hour to Martinborough's wineries. If you are travelling for work, we are only a minute off the main highway.

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, 194 reviews

Tui Suite at Wairarapa's Lakeview Lodge

Welcome to our luxury 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 kitchen and BBQ are available for self-catering.

Top Guest favourite
A heated pool is surrounded by a clean, tile deck and lush greenery, including trees and flowering shrubs. The pool area is fenced for privacy, with steps leading to the well-maintained grounds, creating an inviting outdoor space.
Guesthouse in Woodside
5 out of 5 average rating, 120 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 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!

Popular amenities for South Wairarapa District guesthouses