Guesthouse holiday rentals in Southern Highlands

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Southern Highlands

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Guesthouse in Bowral

4.97 out of 5 average rating, 146 reviews

Bespoke Highlands Cabin

Newly refurbished self-contained cabin combining the beauty of country with the comforts of town. Enjoy trees, abundant bird life, cosy fireplace, luxurious king bed, kitchenette, bath and tv. Exclusive use tennis court; Bowral's best walks at your doorstep; and 5 min drive to fine restaurants, pubs and great shopping. Easy access to Milton Park; Bong Bong Racecourse; Ngununggula Regional Art Gallery; Bradman Museum and Corbett Gardens. Private, cosy and beautiful, it's Bowral's hidden gem.

4–11 Oct

$297 NZD per night

Guest favourite

Guesthouse in Bowral

5.0 out of 5 average rating, 147 reviews

Contemporary self contained apartment, Old Bowral

The Loft on Jasmine is a fully self-contained apartment, just 10 minutes walk from beautiful Bowral in the Southern Highlands of NSW. In the style of 'Old Bowral' the Loft is weatherboard, has raked ceilings, internal lining boards and sky lights. Hydronic heating , heated towel rail and underfloor heating in the bathroom keeps you warm in winter, while reverse cycle air conditioning maintains comfort in summer. There is a separate bedroom, kitchen with continental breakfast and lounge with TV.

8–15 Jul

$244 NZD per night

Guest favourite

Guesthouse in Sutton Forest

4.97 out of 5 average rating, 102 reviews

Kate’s Cottage with spectacular countryside views

A self-contained studio cottage, adjacent to the main homestead with district and country landscape views. The 20-acre property includes treelined walks and a sweeping drystone ha-ha and feature drystone walls. There are numerous places of interest in the surrounding towns and villages. Moss Vale is 6.3kms and Sutton Forest village is 5.6kms. The award-winning Southern Highlands Winery is a 30-minute walk along a beautiful country road. Relax and enjoy this unique and tranquil country getaway.

12–19 Aug

$186 NZD per night

Guest favourite

Guesthouse in Mittagong

4.97 out of 5 average rating, 103 reviews

The Banksias - Stylish & Cosy Highlands Retreat

Cosy up in this contemporary yet homely self-contained, split-level guesthouse, styled with a sleek Australiana feel. A former artist's studio, the space features soaring ceilings and an abundance of natural light. Best of all is the location - The Banksias is a mere 5 minute walk to Mittagong town centre, where fabulous cafes and restaurants await. Also within an easy stroll are Mount Gibraltar and Lake Alexandra with their stunning bushwalking tracks, and only a 5 minute drive into Bowral.

7–14 Apr

$252 NZD per night

Guest favourite

Guesthouse in Bowral

4.94 out of 5 average rating, 114 reviews

Luxemburg Stables Guesthouse - Country Retreat

Newly renovated 38sqm separate dwelling situated away from the main house on a leafy acre set back from the street. This private, open plan space is an easy 1km walk to Bowral shops, cafes, restaurants and station. Close to Cherry Tree Walk that winds around 'Old Bowral' to Bradman Oval with several lovely side walks leading back to town. A very short drive to local wineries, golf clubs and the Mt Gibraltar lookout and walking tracks. Perfect for visiting wedding guests or a country escape.

5–12 Aug

$181 NZD per night

Guest favourite

Guesthouse in Burradoo

4.93 out of 5 average rating, 291 reviews

The Stables at Long Paddock

The Stables is a self contained guesthouse situated on our family property in beautiful Burradoo. Suited to either a family of up to four or two couples, the guesthouse is fully equipped for a weekend away in the countryside. Located midway between Bowral and Moss Vale, the Stables is set on 10 picturesque acres and surrounded by unspoilt farmland, with views to Oxley Hill and surrounds - yet Bowral’s boutiques, homewares stores, restaurants and cafes are just 5 minutes away.

4–11 Jul

$370 NZD per night

Guest favourite

Guesthouse in Bowral

4.99 out of 5 average rating, 349 reviews

Buskers End

This cottage is nestled in a breathtaking 2.5 acre established garden. It is perfect for couples wanting to retreat from the world or it is close to Bowral and surrounding attractions including golf clubs and vineyards. The cottage is well appointed with all necessities, such as tea, coffee and toiletries. Large bathroom with spa bath and separate shower. Fully equipped kitchen Wifi Gas fire Air conditioning We would love you to wander and enjoy this beautiful property.

8–15 Sep

$327 NZD per night

Guest favourite

Guesthouse in Burradoo

4.95 out of 5 average rating, 204 reviews

Coppins Cottage - Your Southern Highlands Stay

A cosy cottage perfect for a weekend away. The cottage sleeps four people but more comfortably two and is separate to the main house, perfectly set up for your privacy. We are walking distance from Bowral centre and a 10-15 minute drive to all the wineries the Southern Highlands has to offer. We are here to make your weekend one to remember, indulge in our cosy cottage, sit back and watch TV and have a glass of wine from your complimentary bottle of wine on arrival.

14–21 Aug

$190 NZD per night

Guest favourite

Guesthouse in Mittagong

4.96 out of 5 average rating, 116 reviews

Chagall's Shed

A rustic hideaway at the bottom of our half-acre garden under gum trees filled with native birds. There's a small private garden at the rear, a sprawling vege patch and the fire pit in front. The 5x8 metre building has a small ensuite and bar fridge. There's no TV but the WIFI is fast and a projector with HDMI connection is discretely placed to project streamed cinema onto the wall. We are just 2km from the town's best cafes and Mittagong Station.

30 Jun – 7 Jul

$185 NZD per night

Guest favourite

Guesthouse in Bowral

4.88 out of 5 average rating, 769 reviews

woodland retreat - guest studio

A chic space with Mt Gibralter as your backdrop, set in a garden full of birdlife and the occasional wallaby. We offer private accommodation, own entry through a shared garden, sitting room with a good selection of books and mags, Wifi and Bluetooth, kitchenette with a dining space, 2 bedrooms and 1 bathroom. Very close to main wedding venues eg Bendooley Estate and Centennial Vineyards. Walking distance to Bowral, and close to Mittagong .

16–23 Jul

$160 NZD per night

Superhost

Guesthouse in Bowral

4.86 out of 5 average rating, 270 reviews

Dunrana Cottage Bowral

Cosy studio cottage lies close to the hub of Old Bowral. Enjoy the 700m stroll to the CBD with its restaurants, cafés and boutiques, gorgeous parks, museums, galleries, vineyards + golf courses. A 50m walk to Cherry Tree Walk and the local swimming pool. This intimate setting is perfect for a romantic weekend away. The cottage has a fully fenced courtyard.

21–28 Aug

$192 NZD per night

Guest favourite

Guesthouse in Bowral

4.97 out of 5 average rating, 331 reviews

The Shed @ Bowral

The Shed @ Bowral is a very comfortable and cosy industrial style studio with lovely garden views and a ‘cool’ private semi enclosed verandah area. Quiet and peaceful location close to the town centre and across the road from the Cherry Tree walking/bike path. The accomodation is an easy 15 minute walk to Bowral town centre and the train station.

15–22 Jul

$173 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Southern Highlands guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Guest favourite

Guesthouse in Mittagong

4.94 out of 5 average rating, 214 reviews

Alfred Studio

22–29 Dec

$184 NZD per night

Guest favourite

Guesthouse in Bowral

4.9 out of 5 average rating, 121 reviews

Beatrice Park - The Annexe

5–12 Apr

$223 NZD per night

Guest favourite

Guesthouse in New Berrima

4.85 out of 5 average rating, 307 reviews

Peppergreen Cottage

31 Aug – 7 Sep

$186 NZD per night

Guest favourite

Guesthouse in Huskisson

4.87 out of 5 average rating, 566 reviews

BEACH PARADISE heart of Jervis Bay!

17–24 Apr

$222 NZD per night

Guest favourite

Guesthouse in Kiama Downs

4.93 out of 5 average rating, 226 reviews

Uninterrupted ocean view, private & quiet. Relax.

8–15 Jun

$405 NZD per night

Guest favourite

Guesthouse in Wollongong

4.94 out of 5 average rating, 422 reviews

Casa Verde: walk/cycle to hospital, train & CBD.

7–14 Feb

$141 NZD per night

Guest favourite

Guesthouse in Engadine

4.94 out of 5 average rating, 139 reviews

Suburban Bush Retreat Guest House

26 Jun – 3 Jul

$146 NZD per night

Superhost

Guesthouse in Kiama

4.75 out of 5 average rating, 355 reviews

Number 1 Reid Street

12–19 Nov

$112 NZD per night

Show all

Guesthouses with a patio

Guest favourite

Guesthouse in Picton

4.95 out of 5 average rating, 131 reviews

Coull Cottage 2-bedroom guesthouse in Picton CBD

29 Jul – 5 Aug

$241 NZD per night

Guest favourite

Guesthouse in Albion Park Rail

4.93 out of 5 average rating, 192 reviews

Modern and Stylish Accomodation with Outdoor Bath

9–16 Sep

$234 NZD per night

Guest favourite

Guesthouse in Minnamurra

5.0 out of 5 average rating, 144 reviews

Harvest Moon Guesthouse-Minnamurra

6–13 Oct

$390 NZD per night

Guest favourite

Guesthouse in Saint Georges Basin

4.83 out of 5 average rating, 149 reviews

Seabreeze Studio (Private Hot Tub / Water Views)

19–26 Jul

$195 NZD per night

Guest favourite

Guesthouse in Bulli

4.97 out of 5 average rating, 111 reviews

Bulli Beach Getaway.

14–21 Jul

$264 NZD per night

Guest favourite

Guesthouse in Vincentia

4.92 out of 5 average rating, 106 reviews

Bamboo Studio located across the road from the beach. Fully self contained and modern amenities. Quite location and small walk to local shops. Perfect for a couples retreat near the beach.

25 Sep – 2 Oct

$287 NZD per night