Best Southern Highlands Getaway: Where to Stay, Eat, Drink & Explore

By KAYAK Australia
© Header photo | Centennial Vineyards, Bowral | DESTINATION NSW

Rolling green fields, verdant vineyards and historic towns have attracted visitors to the Southern Highlands for over 140 years. It’s the perfect place to uncover some of Australia’s most acclaimed restaurants, award-winning cool-climate wineries, antique stores, art galleries and beautiful gardens.

However, the question most visitors still ask before leaving is: Where’s the best place to stay in the Southern Highlands? From Bowral and Mittagong to Moss Vale, Berrima and Bundanoon, these five towns will inspire your next trip with Southern Highlands winery experiences, luxurious day spas, gourmet dining and unique local sights.

Getting to the Southern Highlands

By Car: Approximately 90 minutes from Sydney, arriving in Bowral.
Nearest Airport: The nearest airport to the Southern Highlands is Sydney Airport, about 1.5 hours away via car.
By Train: Approximately one hour and 45 minutes from Sydney, leaving Central Station and alighting in Bowral.

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Bowral

Centennial Vineyards Bowral Southern Highlands
Centennial Vineyards, Bowral | DESTINATION NSW

Bowral is considered the heart of the Southern Highlands and is certainly the largest of all the settlements. It features an array of  wineries, beloved weekend markets and boutiques.

On top of that, it also boasts an enduring cricket culture, centred around the immortal Australian cricketer and local legend, Donald Bradman. Boutique shopping, antique retailers and farm-to-table dining ensure Bowral remains a highlight for leisure and culture lovers alike.

 Incredible Bowral Attractions & Experiences

  1. Bradman Museum & International Cricket Hall of Fame – Six galleries exploring the history of cricket and the accomplishments of Sir Donald Bradman. There are interactive experiences and outstanding collection of memorabilia.
Bradman Museum & International Cricket Hall of Fame
Bradman Museum & International Cricket Hall of Fame, Bowral | DESTINATION NSW
  1. Bowral Art Gallery Hopping – Discover local paintings, sculptures and prints at Milk Factory Gallery, Bowral Art Gallery and more.
  1. Boutique Shopping – Browse local antiques at Dirty Janes Bowral and visit the boutiques in Springetts Arcade.
Dirty Janes, Bowral, Southern Highlands
Dirty Janes, Bowral | DESTINATION NSW

Best Bowral Restaurants & Wineries

  1. LudoFresh and unpretentious dining that accentuates local flavours with smiling hospitality.
  1. Harry’s on Green LaneA laidback eatery filled with travel memorabilia, botanicals and floor-to-ceiling bookshelves.
  1. Centennial Vineyards – Internationally and nationally recognised winery with cellar door tastings, guided vineyard walks and painting classes (with wine of course).

Popular Bowral Accommodation

  1. Gibraltar HotelA 4-star hotel with an 18-hole golf course, fitness centre, indoor pool, day spa and bar and restaurant.
Gibraltar Hotel Bowral, Southern Highlands
Gibraltar Hotel Bowral | Provided by BOOKING.COM
  1. The Sebel Bowral Heritage ParkModern accommodations with a pool, gym and garden about 900 metres from the Bradman Museum & International Cricket Hall of Fame.
The Sebel Bowral Heritage Park
The Sebel Bowral Heritage Park | Provided by ICE PORTAL

Mittagong

Wombeyan Cave Mittagong
Wombeyan Cave | GETTYIMAGES – IGNACIO PALACIOS

The historic town of Mittagong is Sydney’s gateway to the Southern Highlands and home to Australia’s first iron works. Its excellent vine-growing conditions also support more than 6 wineries and cellar doors.

Discover a wealth of Australian history while admiring well-preserved colonial sandstone buildings and visiting antiques and craft centres. Mittagong is also surrounded by three mountain reserves, so nature lovers can get their fix of alpine scenery, glassy lakes and native wildlife. 

Incredible Mittagong Attractions & Experiences 

Lake Alexandra Reserve, Mittagong, Southern Highlands
Lake Alexandra Reserve, Mittagong | DESTINATION NSW
  1. Southern Highlands Winery Tours with The Grape Escape – Taste over 20 wines at renowned cellar doors, including cheese pairings and expert pouring.
  1. Mittagong Antiques Centre – Browse treasures from a bygone era with knowledgeable experts, including jewellery, sculpture, porcelain and toys.
  1. Drive up Mount Gibraltar – Incredible views of Sydney from tranquil picnic spots on the top of Mount Gibraltar.

Best Mittagong Restaurants & Wineries

  1. The Shaggy CowRustic, award-winning cafe with creative dishes showcasing produce from local farms.
  1. Tertini WinesAward-winning, cool-climate winery renowned for its Pinot Noir, Riesling and Chardonnay.
  1. Diamond Creek Estate – Picturesque winery with an olive grove, offering wine and olive tastings.

Popular Mittagong Accommodation 

  1. Fitzroy Inn Historic RetreatA beautifully restored colonial sandstone building housing adults-only accommodation with private balconies, spa baths and breakfast packs.
  1. Old Bank Boutique HotelStylish 4-star Mittagong hotel with a bar, garden, wine cellar and sun-drenched terrace.
Old Bank Boutique Hotel
Old Bank Boutique Hotel | Provided by BOOKING.COM

Moss Vale

Moss Vale, Southern Highlands
Cows grazing in green filed in Moss Vale, New South Wales | SHUTTERSTOCK – PHILLIP MINNIS

The Southern Highlands’ agricultural spirit comes alive in Moss Vale. One of the first settlements, Moss Vale still has strong ties to the Highlands through livestock sales, farmers’ markets and a traditional agricultural show.

Moss Vale also has a prettier side to complement its rugged charm, including picturesque gardens and nature reserves. It also offers modern boutiques, a coveted golf course and various establishments specialising in wine, beer or hearty Australian cuisine.

Incredible Moss Vale Attractions & Experiences

  1. Livestock sale at Moss Vale Saleyards – Head to the Southern Regional Livestock Exchange on Wednesday to witness the high-paced bidding of livestock.
  1. Cecil Hoskins Nature ReserveThis sprawling wetland is home to around 90 species of birds, scenic picnic spots and walking trails. 
  1. Moss Vale Golf Club – An 18-hole championship golf course with challenging turns, creek crossings and immaculate greens.

Best Moss Vale Restaurants & Wineries

  1. BirchInnovative dining meets warm Aussie hospitality at one of the Southern Highlands’ most Instagrammable restaurants.
  1. Mount Ashby Estate – French provincial meets early Australiana at this boutique winery serving homemade dishes at French farmhouse tables outside the restored original dairy.
  1. Southern Highlands Brewing – Locally brewed beer paired with boutique beer house dining in the heart of Moss Vale. 

Popular Moss Vale Accommodation

  1. Peppers Manor HouseGlamorous rural resort with a peaceful gazebo, sprawling pool, garden, multiple restaurants and a lounge with a crackling fireplace.
Peppers Manor House
Peppers Manor House | Provided by BOOKING.COM
  1. Elixir – Luxury on Acreage Enormous private holiday home with four bedrooms, sun terrace, garden, barbecue, gourmet kitchen and nearby ponds.
Elixir - Luxury on Acreage
Elixir – Luxury on Acreage | Provided by BOOKING.COM

Berrima

Berrima, Southern Highlands
Berrima Southern Highlands | DESTINATION NSW

It’s impossible to not feel the charm of Berrima, Australia’s best-preserved Georgian village. Simply strolling down the leafy streets lined with colonial sandstone buildings is pure Southern Highlands joy.

These streets are also lined with alfresco cafes, local boutiques and craft stores. Local art galleries sit side by side with cellar doors and fine-dining restaurants, while the hills surrounding Berrima reveal state forests, award-winning wineries and peaceful waterways. 

Incredible Berrima Attractions & Experiences

  1. Surveyor General Inn – Stop for a cold beer at the oldest continually licensed inn in Australia.
  1. The Berkelouw Book Barn – Read a book by the fireplace in this bookshop/winery while sipping one of the house wines.

Best Berrima Restaurants & Wineries

  1. Eschalot Upscale Modern Australian restaurant set in a heritage stone cottage serving fresh produce grown in on-site gardens.
Eschalot Restaurant Berrima
Eschalot, Berrima | DESTINATION NSW
  1. The Loch – A working farm with a tasting room, beautiful garden, farm produce stall and charming accommodations. 
  1. PepperGreen EstateWinery, restaurant, cellar door, tasting room and olive grove with unique tasting experiences hosted by knowledgeable guides.
PepperGreen Estate Berrima, Southern Highlands
PepperGreen Estate, Berrima | DESTINATION NSW

Popular Berrima Accommodation

  1. Bendooley EstateLuxurious accommodation at a winery estate with full kitchens, living and dining rooms, baths and private terraces.
Bendooley Estate Berrima
Bendooley Estate | Provided by BOOKING.COM
  1. Berrima Bakehouse HotelA budget-friendly motel providing a relaxed country hideaway experience with spacious modern units, a practice golf hole, swimming pool, gardens and barbecues in the centre of Berrima.

Bundanoon

Fitzroy Falls Morton National Park, Southern Highlands
Fitzroy Falls in Morton National Park | GETTYIMAGES – POSNOV

Known locally as ‘Bundy’, Bundanoon is the gateway to Morton National Park, where fascinating rainforest walks, waterfalls and nature await. The best Southern Highlands town for active travellers, it also offers various cycling routes for all levels.

Bundanoon is home to a rich Scottish heritage and culture, best experienced during the annual Bundanoon Highland Gathering. Not to be outdone by the other towns on this list, Bundanoon also has many foodie highlights scattered around the nearby town of Exeter.

Incredible Bundanoon Attractions & Experiences

  1. Wild Horizon Outdoor Tours – Embark on a mountain biking, cross-country skiing or walking trip with experienced guides.
  1. Bundanoon Highland Gathering – Witness pipe bands, Highland dancing, live music, strength competitions and traditional Scottish games. 
  1. Morton National Park Walk or cycle through this national park which is the home to the cascading Fitzroy Falls, scenic lookouts and glow worm caves.

Best Bundanoon Restaurants & Wineries

  1. DeliLicious Bundanoon – Relaxed downtown cafe serving freshly baked pies, fruit and charcuterie boards, cakes and farm-fresh salads. 
  1. Cuttaway Hill – Family-owned winery offering unique experiences, such as varietal wine tasting and wine and charcuterie pairings.
Cuttaway Hill Wines, Southern Highlands
Cuttaway Hill Wines, Exeter | DESTINATION NSW
  1. St Maur Wines – Father-and-son boutique winery known for its Pinot Noir, Cabernet and Merlot made with “modern family practices”.

Popular Bundanoon Accommodation 

  1. Bundanoon Country Inn MotelModern and beautiful rooms with electric blankets and bar fridges. The affordable motel also has a tennis court, swimming pool, gardens, barbecues and one of the best conference facilities in the Southern Highlands. 
  1. Bundanoon LodgeTucked-away lodge with lorikeet feeding, landscapes gardens and rooms with spa baths. 
Bundanoon Lodge Bundanoon
Bundanoon Lodge|Provided by BOOKING.COM

Experience the Best of the Southern Highlands

From Bundanoon to Moss Vale, the Southern Highlands invites you to search far and wide for its most unforgettable experiences. These Southern Highlands attractions, wineries, restaurants and hotels all capture the beauty and hospitality of this unique region.

Book your next Southern Highlands getaway through KAYAK for the best deals on hotels.

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