Guesthouse vacation rentals in Southern Highlands

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Top-rated guesthouse rentals in Southern Highlands

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

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Guest favorite

Guesthouse in Bowral

4.97 out of 5 average rating, 147 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.

Aug 24 – 31

G$32,506 GYD per night

Guest favorite

Guesthouse in Bowral

5.0 out of 5 average rating, 148 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.

Nov 3 – 10

G$29,295 GYD per night

Guest favorite

Guesthouse in Sutton Forest

4.97 out of 5 average rating, 103 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.

Jul 17 – 24

G$22,523 GYD per night

Guest favorite

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.

Nov 21 – 28

G$29,994 GYD per night

Guest favorite

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.

Jul 30 – Aug 6

G$21,451 GYD per night

Guest favorite

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.

Jul 13 – 20

G$44,351 GYD per night

Guest favorite

Guesthouse in Bowral

4.99 out of 5 average rating, 352 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.

Oct 4 – 11

G$39,345 GYD per night

Guest favorite

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.

Oct 4 – 11

G$23,674 GYD per night

Guest favorite

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.

Jun 24 – Jul 1

G$21,430 GYD per night

Guest favorite

Guesthouse in Bowral

4.88 out of 5 average rating, 772 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 .

Jul 1 – 8

G$18,931 GYD per night

Superhost

Guesthouse in Bowral

4.86 out of 5 average rating, 271 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.

Apr 25 – May 2

G$23,339 GYD per night

Guest favorite

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.

Jun 6 – 13

G$19,223 GYD per night

Vacation rentals for every style

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Popular amenities for Southern Highlands guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guest favorite

Guesthouse in Mittagong

4.94 out of 5 average rating, 215 reviews

Alfred Studio

Oct 9 – 16

G$21,435 GYD per night

Guest favorite

Guesthouse in Bowral

4.9 out of 5 average rating, 121 reviews

Beatrice Park - The Annexe

Sep 11 – 18

G$25,389 GYD per night

Guest favorite

Guesthouse in New Berrima

4.85 out of 5 average rating, 307 reviews

Peppergreen Cottage

Sep 6 – 13

G$23,206 GYD per night

Guest favorite

Guesthouse in Berry

4.92 out of 5 average rating, 295 reviews

Windsor Cottage

Mar 7 – 14

G$29,964 GYD per night

Guest favorite

Guesthouse in Callala Bay

4.92 out of 5 average rating, 604 reviews

JERVIS BAY STUDIO & SPA- walking distance to shops

Nov 1 – 8

G$30,762 GYD per night

Guest favorite

Guesthouse in Huskisson

4.87 out of 5 average rating, 566 reviews

BEACH PARADISE heart of Jervis Bay!

Sep 17 – 24

G$24,852 GYD per night

Guest favorite

Guesthouse in Wollongong

4.94 out of 5 average rating, 423 reviews

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

Apr 24 – May 1

G$17,540 GYD per night

Superhost

Guesthouse in Kiama

4.75 out of 5 average rating, 355 reviews

Number 1 Reid Street

Nov 12 – 19

G$13,939 GYD per night

Show all

Guest house rentals with a patio

Guest favorite

Guesthouse in Picton

4.95 out of 5 average rating, 132 reviews

Coull Cottage 2-bedroom guesthouse in Picton CBD

Dec 29 – Jan 5

G$30,001 GYD per night

Guest favorite

Guesthouse in Albion Park Rail

4.93 out of 5 average rating, 195 reviews

Modern and Stylish Accomodation with Outdoor Bath

Aug 22 – 29

G$27,192 GYD per night

Guest favorite

Guesthouse in Minnamurra

5.0 out of 5 average rating, 144 reviews

Harvest Moon Guesthouse-Minnamurra

Jan 25 – Feb 1

G$48,548 GYD per night

Guest favorite

Guesthouse in Bulli

4.97 out of 5 average rating, 111 reviews

Bulli Beach Getaway.

Aug 27 – Sep 3

G$32,887 GYD per night

Guest favorite

Guesthouse in Sussex Inlet

4.88 out of 5 average rating, 131 reviews

ADORABLE STUDIO ROOM RIGHT IN THE HEART OF TOWN

Mar 31 – Apr 7

G$16,562 GYD per night

Guest favorite

Guesthouse in Vincentia

4.93 out of 5 average rating, 107 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.

Sep 11 – 18

G$33,751 GYD per night