Vacation 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.

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.

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.

Hopewood Cottage | Architecturally Designed

Designed by award-winning Tziallas Architects, this cottage is in a prime location! This gorgeous one-bedroom features a full chef's kitchen, a luxury king-sized bedroom, outdoor spaces to relax, and private off-street parking. An abundant potager garden is perfect for guests to wander and harvest seasonal fruits, vegetables, and herbs. Hopewood Cottage is located close enough to walk to pubs, restaurants and cafes, but tucked away from the hustle and bustle of town. insta: @hopewood_cottage

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 Cottage: luxury & Heritage in Bowral's heart

Immerse yourself in the quintessential Bowral lifestyle. 'THE COTTAGE' combines historic elegance & charm with custom curated equine themed luxury decor brands, positioned perfectly for those attending weddings, exploring 'Tulip Time' or seeking a sophisticated village haven. This spacious & cosy 3 bedroom home accommodates 6 guests in the exclusive high-end 'old Bowral', featuring a ready-to-light fireplace, a large entertaining deck & a quiet, tranquil tree-lined central location to the CBD

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.

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.

Stroll to Bowral, Cherry Tree Walk, Mt Gibraltar

This newly-renovated, light, private guest suite is in a quiet area, in walking distance of pool, cafes, Bowral town centre and train station. If the Cherry Tree Walk and bush walks up Mount Gibraltar are appealing, this is for you. You will have separate access into a comfortable lounge room. There is a gas fireplace. The kitchenette has a bar fridge, microwave, coffee and tea facilities. You have a private courtyard off the bedroom, which has a fan and air conditioner.