Holiday rentals with outdoor seating in Bowral - Mittagong

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.

The Chapel at Welby Park Manor

Recently renovated. Built in the 1870's, Welby Park Manor is one of the oldest homes in the Highlands. The Chapel is a freestanding sandstone guest cottage with private entry and outdoor area. The property is a two-minute drive from the Mittagong shops, a seven-minute drive to both Bowral and Berrima, and close to local wineries and restaurants. The newly renovated bathroom was completed December 2025 and has under floor heating and heated towel rail, kitchenette & cast iron outdoor fire.

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.

Little Gem at Retford Park Estate. Bowral-5 Min

New apartment located in the prestige "Redford Park Estate" a walk away to the heart of Bowral or 2 min drive to its Restaurants, cafes, boutiques, parks, museums, galleries, vineyards and golf courses.Also 5 min walk within the Estate to visit the Regional Gallery & cafe and explore the stunning gardens and House at "Retford Park", National Trust. The space it is modern, airy , relaxing and stylish. Main bedroom- King bed. Living with large queen sofa bed. Warm and cosy, just come and relax

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.

The Hidden Door Bowral Villa -the❤️of Old Bowral

Our architect designed Villa is a flat 3 minute walk to the heart of Old Bowral with 2 bedrooms featuring new Super King Bed and new King Bed that can be split into Two Single Beds. Perfect for golfing weekends, wedding guests, girls' weekends, romantic weekends, families and business travellers etc. We are also Pet Friendly. For larger groups, we have 3 properties which are only a couple of minutes walk from the heart of Old Bowral that can accommodate up to 14 people as detailed below.

"The Burrow", Mittagong, Southern Highlands, NSW

“The Burrow” is a self-contained cottage on a 100 acre wildlife sanctuary just 5km from the centre of Mittagong. Once you arrive, it's just you and a few hundred kangaroos and a wombat or two. We invite you to take in nature at your own pace in this peaceful & private setting. “The Burrow” is a hand-built, mud-brick cottage set on the Southern Highlands of NSW. It's quirky yet very comfortable. With nature & wildlife all around we want you to feel like you're 1000 miles from anywhere.

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.

Little Rosewood - Charming Private Cottage Bowral

Whether it's you’re first visit or a return stay at our blissful hideaway in the garden, you’ll always feel as if you’ve stumbled upon something special. Our delightfully appointed cottage is cosy and intimate, with the perfect amount of room for you to steal away by yourself, with the one you love, a girls' get together or with special friends or family. Close to everything the Highlands has to offer, yet quiet and tucked away, it's truly an escape from the city!

Lulu's Cottage – a hidden gem. Easy walk to CBD

Lulu's Cottage is charming and spacious, with 2 queen-size bedroom (the Main with ensuite) and the third with 2 single beds (can be King but MUST be requested at time of booking) located at the front of the house. The living area to the rear leads onto a large covered back deck where you can relax overlooking the leafy garden. The cottage has a fully equipped kitchen and is a short easy walk to/from Bowral Village. No Smoking and minimum 2 nights stay.

Southern Highlands Get-a-Way —Breakfast Supplies—

A pet friendly, comfortable and well-appointed, self-contained apartment for rent amongst the gum trees. Only a short walk to Mittagong train station, Sturt Gallery, shops, restaurants and galleries. Newly renovated, the apartment has reverse cycle air-conditioner, a private entrance, designated parking area and a private outdoor outlook. Wi-fi and Netflix all included. Comfortable, private, quiet get-a-away so stay a week or more. No cleaning fee.

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 .