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Guesthouse vacation rentals in South Wairarapa District

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Top-rated guesthouse rentals in South Wairarapa District

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

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Guesthouse in Greytown

4.8 out of 5 average rating, 167 reviews

The Brambles

Greytown has become a Mecca for boutique shopping and has some great restaurants & cafes. We are a 15min drive from Martinborough full of wineries & olive groves The Brambles is a lovingly restored 1800's outbuilding converted into a small cottage in a rural and peaceful setting. Great indoor outdoor flow to a private BBQ area, in the cottage kitchen there is a microwave, a Nespresso machine with some coffee pods & milk supplied, a 2 element electric hob and all the pots & pans you need to cook

Feb 24 – Mar 3

R1,932 ZAR per night

Guesthouse in Upper Hutt

4.92 out of 5 average rating, 115 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 mins from the Waiarapa, the wine trail & the many cafes, restaurants & boutique shops. Wellington & all that this vibrant city has to offer is a 40 mins drive.

Oct 19 – 26

R1,371 ZAR per night

Guesthouse in Masterton

4.92 out of 5 average rating, 606 reviews

Studio 8

My place is close to restaurants and dining, family-friendly activities, public transport, shopping. You’ll love my place because of Its proximity to town, the studio is a short 2 min walk from the Queen St shopping precinct, great cafes and restaurants and only a casual 5 min stroll to QEll Park. The two storied Studio is tucked in behind the 1879 cottage with its own private deck, comfortably appointed for couples seeking a Wairarapa getaway or business travellers needing a central location.

Sep 3 – 10

R1,507 ZAR per night

Guesthouse in Carterton

4.91 out of 5 average rating, 211 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.

Jan 7 – 14

R1,402 ZAR per night

Guesthouse in Carterton

4.99 out of 5 average rating, 154 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 3, 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.

Jan 18 – 25

R2,523 ZAR per night

Guesthouse in Upper Hutt

4.97 out of 5 average rating, 253 reviews

Oak Tree Cottage

Welcome to Oak Tree Cottage A Newly built 30m2 cottage set at the rear of our property. Located in the Heretaunga/Silverstream area of Upper Hutt. Close to all transport links train/bus/motorway.A well equipped kitchenette allows for cooking with continental breakfast provided. The cottage is warm and quiet with double glazing and a heat pump/aircon. Private entrance and courtyard . Walking distance to Trentham Race course,Royal Wellington golf course and Fig tree cafe.

May 10 – 17

R1,932 ZAR per night

Guesthouse in Martinborough

4.98 out of 5 average rating, 132 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

Jan 31 – Feb 7

R3,051 ZAR per night

Guesthouse in Western Lake

4.99 out of 5 average rating, 129 reviews

Tui Suite at Wairarapa's Lakeview Lodge

Welcome to our luxury peaceful bed & breakfast escape. 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 and relax. Tui Suite at Lakeview Lodge is just 60 minutes from Wellington. Single nights available weekdays, no cleaning fees, a continental breakfast is included, and a kitchen and BBQ are available for self-catering.

Nov 19 – 26

R3,340 ZAR per night

Guesthouse in Woodside

5.0 out of 5 average rating, 104 reviews

Historic Cottage getaway 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 cruiser bikes and 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!

Jan 22 – 29

R2,270 ZAR per night

Guesthouse in Featherston

4.97 out of 5 average rating, 487 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 kune kune pig (Sophie), puppy (Lucy), donkeys (Phoebe & Anna) and August the cat.

Aug 28 – Sep 4

R1,111 ZAR per night

Guesthouse in Greytown

4.95 out of 5 average rating, 100 reviews

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. A small foldaway bed is available at an additional fee for a child under 12.

Jun 10 – 17

R1,514 ZAR per night

Guesthouse in Martinborough

4.9 out of 5 average rating, 248 reviews

A charming room in a country garden setting.

Studio 25 is a charming room in a country garden setting. It is right next door to an accessible vineyard (with tasting room) and only 5 minutes stroll from town. Facilities include heat pump, TV, ensuite shower and toilet, and basic kitchen facilities (fridge, microwave, toaster, etc.) It is ideally situated as a venue from which you can experience Martinborough hospitality.

Apr 16 – 23

R1,406 ZAR per night

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Popular amenities for South Wairarapa District guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guesthouse in Greytown

4.94 out of 5 average rating, 87 reviews

Westwood Pool House (can sleep 4 Adults)

Jul 25 – Aug 1

R2,359 ZAR per night

Guesthouse in Upper Hutt

4.94 out of 5 average rating, 95 reviews

'The Cottage'

Feb 8 – 15

R1,648 ZAR per night

Guesthouse in Martinborough

4.81 out of 5 average rating, 277 reviews

HawkRise cottage

Jul 1 – 8

R1,745 ZAR per night

Guesthouse in Greytown

4.92 out of 5 average rating, 26 reviews

Westwood Country House

Jun 13 – 20

R13,026 ZAR per night

Guesthouse in Carterton

4.85 out of 5 average rating, 212 reviews

The Buzzy Garden B&B

Mar 13 – 20

R1,284 ZAR per night

Guest house rentals with a patio

Guesthouse in Upper Hutt

4.83 out of 5 average rating, 117 reviews

Adorable guesthouse with hot tub and home gym

Jun 6 – 13

R1,314 ZAR per night

Guesthouse in Upper Hutt

4.98 out of 5 average rating, 49 reviews

Remutaka Retreat. Private Cottage.

Oct 12 – 19

R1,620 ZAR per night

Guesthouse in Martinborough

4.95 out of 5 average rating, 19 reviews

Tuscan Haven - entire guesthouse, no cleaning fee

May 4 – 11

R2,463 ZAR per night

Guesthouse in Dyerville

4.93 out of 5 average rating, 75 reviews

Cottage @ The Groves

Sep 10 – 17

R2,575 ZAR per night

Guesthouse in Greytown

4.98 out of 5 average rating, 42 reviews

The Castle - Greytown

Sep 10 – 17

R1,901 ZAR per night

Guesthouse in Greytown

4.71 out of 5 average rating, 17 reviews

Green Door Cottage - Cosy, Stylish, Serene

Jul 13 – 20

R1,862 ZAR per night

Guesthouse in Carterton

4.97 out of 5 average rating, 87 reviews

The Alchemist Retreat, Private Studio in Carterton

Aug 14 – 21

R2,207 ZAR per night

Guesthouse in Carterton

4.84 out of 5 average rating, 50 reviews

Stylish hideaway on High Street - Carterton

Aug 29 – Sep 5

R1,874 ZAR per night

Guest house rentals with a washer and dryer

Guesthouse in Upper Hutt

4.84 out of 5 average rating, 192 reviews

Semi -Detached Studio

Jul 2 – 9

R863 ZAR per night

Guesthouse in Paraparaumu

4.91 out of 5 average rating, 102 reviews

NGAHUIA - Self-contained Studio

Dec 24 – 31

R1,623 ZAR per night

Guesthouse in Upper Hutt

4.94 out of 5 average rating, 117 reviews

Beautiful 1 bedroom cottage!

Nov 20 – 27

R2,382 ZAR per night

Guesthouse in Masterton

4.89 out of 5 average rating, 132 reviews

Cosy self-contained guest suite

Apr 13 – 20

R979 ZAR per night

Guesthouse in Upper Hutt

5.0 out of 5 average rating, 17 reviews

The Bristol Palace

Jan 17 – 24

R1,580 ZAR per night

Guesthouse in Upper Hutt

4.96 out of 5 average rating, 69 reviews

Comfortable one bedroom guest house, free parking

May 22 – 29

R1,398 ZAR per night

Guesthouse in Greytown

4.94 out of 5 average rating, 17 reviews

Orchard Road Guest Suite

Jun 7 – 14

R2,138 ZAR per night

Guesthouse in Parkvale

5.0 out of 5 average rating, 11 reviews

Fallen Oaks Cottage, Carterton

Aug 1 – 8

R3,863 ZAR per night

Destinations to explore