From magical small country villages and coastal havens to wine regions steeped in centuries of history, regional NSW has no shortage of picture-perfect travel destinations. As the gateway to so many incredible places, wedged firmly between mountains, coastal regions and rolling valleys, Sydney affords its locals direct access to some of the nation’s most beautiful spots for weekend getaways. So much so that it would be a shame not to take full advantage of its central spot on the map.
Like picking a favourite child, it’s near impossible to lay claim to the best regional towns in NSW, but in the name of science, we’ve narrowed it down to six.
1. Berry, NSW
Voted Best Small Town in the NSW Top Town Awards, Berry may no longer be the NSW South Coast’s ‘best kept secret’, but it is still simply the best.
A precise and beautiful blend of country and coast, of village charm and city bustle, Berry is the perfect place to escape the hustle and bustle of the city, with plenty of reasons to visit.
What to do in Berry, NSW
The picturesque town is a popular escape for glamorous Sydneysiders, offering epicurean adventures, stunning nature destinations and a touch of history. It boasts an award-winning winery in Two Figs, locally-made gourmet wares and famous baked goods, like those from Milkwood Bakery (one of the best country bakeries in NSW if you ask us!) and the famous Berry Donut Van. The town is also perfectly located near beaches and nature trails like Seven Mile Beach, Sand Track Loop Walk and Drawing Room Rocks Trail.

Where to stay in Berry, NSW
There is no lack of stylish accommodation in the Shoalhaven region either. With quaint country cottages to farm retreats, you can stay in the charming Bundara Farm alongside mini horses and cattle, or the Neale Whitaker-designed Taylors of Berry and enjoy commanding views of the escarpment and beyond.
From Sydney, Berry is an easy two-hour amble down the Princes Highway, or just over two hours from Canberra, making it a great spot for a short weekend away.
Striking and charming in equal measure, these are some of the best Berry Airbnbs to make you swoon.

The rooms at Bundara Farm are drenched in sunlight, thanks to the gorgeous original colonial-style windows. (Photography: Abbie Melle | Story: Country Style)
2. Milton, NSW
Antiques and arts, boutique shopping and gourmet experiences await in the picture-perfect country town of Milton, located on the South Coast in the Shoalhaven region. This charming historic village is situated around a three-hour drive from both Canberra and Sydney.
What to do in Milton
The bucolic, coastal town is a charming mix of old and new, and is the ultimate foodie destination of the South Coast. From bakeries and wineries to kitchen garden restaurants and more, there’s no shortage of enchanting local eateries to explore.
Once you’ve had your fill, explore beautiful bush walks with spectacular views like Pigeon House Mountain or Mt Bushwalker in Little Forest Plateau, and find your zen with spots for yoga and meditation along the way.

Where to stay in Milton
And then there are the town’s serious style credentials, with thriving boutique hotels and clothing and homewares stores upping the style points. Stand-out stays include The Stables at The Old Schoolhouse Milton and Gwen, by Washerwomans Social Club.
Tucked between the neighbouring towns of Nowra and Ulladulla, if you’re planning your visit already, here are the most stylish Airbnbs in the majestic South Coast town of Milton.

3. The Blue Mountains, NSW
At just over an hour’s drive west from Sydney, the Blue Mountains is a popular day trip destination for Sydneysiders hoping for fresh air, a glimpse of the mountains and respite from the everyday.
What to do in the Blue Mountains
As its name may imply, the region is best known for its soaring mountainous sandstone ridges and enchanting natural beauty, with valleys, rock formations, and craggy cliffs all blanketed by native bushland.
For nature buffs, the World Heritage-listed national park has it all: endless vistas, Australian wildlife, and walking trails through lush rainforest with plenty of spectacular waterfalls.

Where to stay in the Blue Mountains
From luxe retreats to cosy weatherboard cottages, like Edwina Bartholomew’s cottage, Warramba, take the day off at these Blue Mountains accommodation options where you can rest and recover for another day of exploring.

4. Hunter Valley, NSW
The Hunter Valley is a wine region steeped in tangible history, with roots that can be traced back 200 years, when the Hunter became one of the country’s first commercial wine regions. With numerous c1800s cottages and huts still standing, a quick stroll down the high street is like stepping back in time.
What to do in the Hunter Valley
Famous for its production of Semillon and Shiraz, vines in the Hunter were first planted in 1823. But the focus now is on its future.
You could stay in the Hunter for weeks and never visit the same spot twice, considering it boasts more than 150 cellar doors, and that’s not including the numerous restaurants, tasting experiences, spas, trails, national parks, golf courses and art trails that are waiting to be explored.

Where to stay in the Hunter Valley
Visitors to the region have plenty of stylish accommodation options, ranging from cosy log cabins to lovingly restored sandstone cottages, and of course, no shortage of vineyard stays. Bringing the extended family? Consider booking a private luxury farm stay at Wallaringa, a modern farmhouse that sleeps up to eight guests.
Just two hours north of Sydney, grab your picnic basket and wine bottle chillers and escape for a weekend of wine at these beautiful Hunter Valley stays.

5. Orange, NSW
Sharing its name with a citrus fruit but famously a grape-growing region, the paradoxical town of Orange is an unforgettable country escape.
It was named after the Prince of Orange, with whom the NSW Surveyor General served in the Peninsular War, but these days the chilly town is abuzz with acclaimed wineries, cellar doors, trendy cafes, and homewares boutiques.
What to do in Orange
Renowned for its crisp, cool climate wines and produce, Steve Cordony’s former country property, Rosedale Farm, and being the birthplace of Australian poet Banjo Paterson, Orange is well worth the 250km journey west of Sydney for any wine, culture or nature savant.
Orange is also the home of Food of Orange District (FOOD) Week, Australia’s longest-running regional food festival, which showcases farmers, local chefs, cooks, restaurateurs and caterers. It is held annually in April and is a must for food-lovers.

Where to stay in Orange
Don’t start packing your bags without first checking out this list of places to stay in Orange! For historic charm and a conveniently central location, be sure to check out Yallungah Boutique Hotel, or if you’re travelling in a large group, consider booking the ultra-stylish SONA, a former bank-turned-holiday house.

Rosedale Farmstay. (Photography: Abbie Melle | Stylist: Steve Cordony | Story: Country Style)
6. Byron Bay
Travel a little further north, and you’ll soon find yourself in the coastal town famous for its surf breaks, stunning coastal scenery and hordes of celeb homes. This laid-back beach town attracts close to two million visitors per year, and it’s not hard to see why.
What to do in Byron Bay
Byron Bay’s idyllic landscape, pristine beaches and laid-back lifestyle have become synonymous with an escape from busy life. The town boasts incredible beaches, stunning hikes with waterfalls like Minyon Falls, and the lively Byron Markets. If you’re looking to do some retail therapy, you’re also in luck; Byron is home to a number of incredible Australian fashion labels. Once you’ve shopped till you’ve dropped, be sure to enjoy a meal at one of the many great restaurants in town, like Light Years, Moonlight Japanese or The Hut.

Where to stay in Byron
From its rolling hinterland farm stays to beachfront shacks perched upon unbroken coastline, Byron has no shortage of luxe accommodation options. Here we share some of Byron’s best boutique stays, which include the retro-style Sun Ranch and Raes on Wategos.
There is a lot to be said for these stunning road-trip destinations, but it would be remiss of us not to spare a thought for the dedicated pet owners. Treat you and your pup to some well-deserved R&R at these pet-friendly stays in regional NSW.

Photo: Bundara Farm