Holiday rentals with outdoor seating in Bowral

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.

Bradman Studio -tranquil garden, easy walk to town

Host of the Year Finalist 2025! Located in the charming Old Bowral precinct, Bradman Studio is a level, easy 10 min walk to Bowral's main street and only 100m from picturesque Bradman Cricket Oval. Spacious open layout, abundant natural light and wide views over our mature, very private rear garden. Adjoining deck for outdoor dining. A/C and double glazed windows assure comfort year round. KS bed, heated bathroom floor, beautiful quality bedlinen & well equipped kitchenette. On-site EV charger.

29 on Shepherd

29 On Shepherd is a small original 1940’s , cosy cottage within easy walking distance to the centre of Bowral. The owner lives in the back 2 storey extension connected by a solid door with total privacy for both and is often away. Noise is not an issue! The two guest bedrooms have one king and 2 king single very comfortable beds, reverse cycle air conditioning, overhead fans, and wardrobe space. A full bathroom with bath, shower and toilet + powder room. Kitchenette, eating area and lounge.

La Colline, bushland retreat

La Colline is a spacious, secluded and well appointed loft studio on the first floor at one end of my house with a large balcony overlooking tall trees on my 2 acres property. Very quiet location, surrounded by nature, yet close to town and all the "goodies" the beautiful Southern Highlands have to offer: vineyards, golf courses, bushwalking tracks, cycling routes, ... Private entrance, a complete kitchen, your own bathroom and toilet, this sunny apartment is perfect for short or long stays.

Luxury Country Escape at Colyersdale Cottage

Set on a 350 acre cattle property 10 minutes from Moss Vale you will find this purpose built, luxurious Hampton’s style cottage. With a 2 car connected garage and indoor/outdoor sandstone fireplace, it comprises 2 large king bedrooms each with a walk-in robe and ensuite. There is ducted air conditioning, fully appointed kitchen, open plan living dining, concealed laundry, outdoor dining terrace, swinging seat and BBQ. Perfect for 2 couples or a family of 4 or 5. Message me for longer stays.

Chic Artist Studio in the Beautiful Bowral.

You'll love this unique and romantic escape. Walking distance to the beautiful town centre of Bowral. This artist studio is a private studio with barn style interior that is super cute and romantic. Close to the wonderful shops, pubs and restaurants of Bowral with off street parking included. The studio has 1 separate bedroom. There is a double sofa bed in the living room that can sleep 2 additional people comfortably. This is not a separate room. This is great for a family with kids.

Contemporary Rural Luxury in Lush Garden

Nestled on the edge of beautiful Bowral, this contemporary two-bedroom space is your idyllic escape. Enjoy modern amenities, including an EV charger, in our stylish and sunny self-contained Guest Wing. Your backyard? Step out onto stunning walking trails in Mansfield Reserve and immerse yourself in nature's serenity. And you're just a 10-minute drive from Bowral's vibrant cafes and shops. This property offers the perfect blend of rural tranquillity and urban convenience.

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.

Ardleigh Cottage in Berrima Village

Situated in the heart of historic Berrima, Ardleigh Cottage offers the discerning traveller all of the comforts of home in a tranquil and relaxing garden setting. Quiet yet very close to the many attractions of Berrima, this private abode is the perfect place for your Highlands stay. A historic pub, a cellar door, galleries, speciality shops, cafes, restaurants, historical places of interest and beautiful bush walks are all within walking distance from the cottage.

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.

The Little House - Pet friendly*/Mid-week special!

While 'house' might be a stretch for this cosy studio-style room, it does have separate facilities. There's a separate "kitchenette", shower and toilet. IT HAS ONE KING SIZE BED and ONE SOFABED. The sofabed is charged at an additional $20/night. The Little House has everything you need for a short stay in The Highlands! * The property welcomes gentle, well socialised pups. The Little House backyard is also shared by my super friendly dog and ewe!

The Potting Shed at Bunya House Bowral

The Potting Shed at Bunya House is a purpose built guest accommodation with every amenity covered to make your stay in Bowral an enjoyable one. Positioned overlooking a beautiful vegetable garden designed by renowned Australian garden designer Paul Bangay The Potting Shed Polished concrete floors, weatherboard walls, a King bed that can be split into King Singles, a kitchenette with breakfast making facilities. Walk to town.