Vacation rentals with a pool in Masterton District

A Little Bit Special

The “Garden Shed’ is a country haven furnished to a high level yet lies just minutes drive to the cafes, gallery, restaurants & parks of Masterton. Take your wine onto the huge deck or ease into the outdoor bath and enjoy the vast galaxy that is the Wairarapa Dark Sky Reserve. You’ll find a coffee machine, microwave, Bluetooth speaker, Apple TV & WIFI. Wander across a paddock & discover the owner’s NZ Gardens Trust 5 Star Garden of National Significance. You’re very welcome to enjoy the pool.

The Good End of the Shed.

A world away from the world -Just 5 mins from Greytown. Situated on a small organic farm in a beautiful garden. Super comfy bed, stylish, mid century decor. Wake up to birdsong, star-gaze from the outside bath while listening to the call of the Ruru. Loll by the pool or borrow the bikes to go exploring. Free breakfast of good coffee, homemade muesli & fruit, artisan bread and spreads. Free-range eggs & bacon available for you to cook for $25 pp. Drive on parking, heat pump, wifi & tv.

The Victorian Villa - Masterton

This 1907 Victorian Villa built entirely of beautiful New Zealand native timber features five bedrooms, four of which are currently set up for guests. (two queen, one double and two single beds) Located on popular Renall Street it's only a short 5-10min walk to Renall Street Train Station or to Masterton's town center where you'll find cafes, shops, cinema and restaurants. Or take a day trip to Wairarapa's iconic beaches- Castlepoint and Riversdale, both are only a 45min drive away.

Hidden Valley Getaway

Hidden Valley Homestay, more commonly known as "The Winery", was once a working vineyard/ winery, known as the Hidden Valley Vineyard. The winery building was built in 1999 out of strawbales. Current owners, and your hosts, Bridget and Jono Hartnell (who live onsite) have recently converted this characteristic building into a fully functional, modern and charming house. Spacious in size, this nearly 200 square metre house is the perfect getaway for family and friend groups.

Riversdale/Homewood Farm Retreat

This fully restored 1870’s one bedroom cottage is waiting for you to enjoy. Located on a historic sheep and beef farm, this cute cottage was originally built for the station cook and in later years has housed the overflow of family guests until its full refurbishment in 2018. Come and relax in the luxurious surroundings away from civilization. The cottage is located on a picturesque part of the Wairarapa coast which has been in the current owners family since the 1870’s.

Summer is here. The Pool is open.

Modern settler cottage on historic Wairarapa property. Hosted by Brigid and Richard. Sleeps up to 8, DIY breakfast. Well-equipped kitchen. Continuous hot water. Unlimited Wifi, 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.

Apt Le Petit. Ideal for a quiet getaway.

Very private and petit but centrally located with a 2 minute walk to the Greytown shops. Ideal for dining out or that morning brunch, with all restaurants and cafes within strolling distance. Perfect location for wedding 'bus pick ups' Although attached to the main house, you have your own separate entry to the apartment which is situated in lovely garden surrounds. There is plenty of off street parking and if you’re feeling energetic there are 2 bikes available.

Fresh oasis near the heart of Masterton

This spacious self-contained apartment is central for Masterton and the Wairarapa region. Town is 800m away & within 20-45mins you can be at Mt Bruce, Castlepoint, Riversdale, or Greytown & Martinborough for vineyards & boutique shopping. Ideal for a couple; with the addition of a king single sofa-bed in the lounge. The bathroom is accessed via the bedroom. Convenient carparking is right on the street, with the option for off-street parking by request.

Heritage 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). Pls note the cottage is attached to the main house but with private access. Discover Greytown's charm and the beauty of Wairarapa. Book now for a serene getaway!

Fantail Cottage, Greytown

Recently named a 2025 Best Family Stay finalist, Fantail Cottage is perfect for relaxing, refreshing, and reconnecting. This spacious 3-bedroom home features beautiful grounds, mature trees, a heated plunge pool (Nov–Mar), spa, indoor and outdoor fires, and wrap-around decks. Enjoy a fully equipped kitchen, separate laundry, and a ground-floor master with ensuite. Upstairs offers two large bedrooms and a full bathroom with separate bath and shower.

Greytown Urban Retreat

Welcome to "Greytown Urban Retreat' our little peace of centrally located paradise. You will love our peaceful oasis, surrounded by lush greenery just 5 minutes walk to the stylish, boutique village of Greytown. Perfect for Summer and Winter - modern, new & double glazed. Pool, outdoor loungers, pickle ball and a fan for the summer and Spa, heater, books, board games for winter. Plus…’Cherry on the top’ - Outdoor Fire for all seasons!

Central Masterton Sleepout with Pool

Keep it simple at this peaceful and centrally located sleepout in Masterton. Only a short walk to the main street shopping precinct which includes some great bars and restaurants. This sleepout provides everything you need for a night or two away in the Wairarapa. It's tastefully decorated with Queen bed, double glazing and its own entrance for easy self check-in and check-out. Tea and Coffee / WiFi & Freeview provided.