5 Winter Escapes
Perfect weekend destinations with an easy drive, fewer crowds than peak season and real cold-weather appeal.
Cosy Winter Weekends
Last updated
For a weekend away from the city we’re looking for a pub fire, a cellar door to duck into, misty valley views and villages that are prettier when it’s quiet. At the same time, we want somewhere busy enough that the cafes, shops and restaurants are open and there’s plenty of accommodation available.
These five villages were all hand-picked from our Next Escape destinations because they deliver for a perfect winter weekend out of the city, and all within driving distance of Sydney. Within each section you’ll find links to the full Next Escape guides for each destination, these include complete guides on where to explore, eat and stay to plan your weekend. We’ve also included featured accommodation in each destination. These are places we’ve personally stayed at and absolutely loved.
Next Escape is your guide to real places and real experiences, with practical, independent travel advice based on first-hand visits: the places we’ve explored, the restaurants we’ve eaten at and the walks we’ve done. This page may contain affiliate links; if you book or buy through them, Next Escape may earn a small commission at no extra cost to you.
Bowral
From Sydney: 1 hour and 30 minutes (118 km)
Bowral has quality dining, beautiful gardens and an easy country getaway feel. Boutique shopping, nearby wineries and a strong food-and-wine scene make it a good fit for couples, food lovers and anyone after a refined but relaxed escape. In winter the tulip season crowds are gone and you’ll find it quieter, with quality restaurant and accommodation bookings a little easier to come by.
There are several excellent cool-climate wineries nearby, as well as other small towns like Berrima and Bundanoon to explore, making it easy to fill a weekend.
READ THE FULL NEXT ESCAPE GUIDE TO BOWRAL →
OUR FAVOURITE ACCOMMODATION
Berida Hotel
A gorgeous boutique hotel located just on the outskirts of Bowral, the Berida Hotel is a relaxing, comfortable, luxurious stay. With Bistro Sociale and Aspinalls Bar & Lounge on-site you could almost spend your entire Bowral weekend cosied up inside. The breakfast is generous and delicious, ideal to set you up for a winter day exploring.
Kangaroo Valley
From Sydney: Around 2 hours and 15 minutes (157 km)
Kangaroo Valley gives you a practical mix of village browsing, wildlife, walks, waterfalls, lookouts and river activities. While Kangaroo Valley is known for its stunning natural setting (national parks, waterfalls, rivers and walks) these can work just as well in winter if you are rugged up. The valley is perfect for misty mornings, waterfalls running harder after rain, and pub meals at The Friendly Inn to warm up afterwards.
Fitzroy, Belmore and Carrington Falls are all easy day-trip additions and look their best when there’s been recent rainfall.
READ THE FULL NEXT ESCAPE GUIDE TO KANGAROO VALLEY →
OUR FAVOURITE ACCOMMODATION
Wildes Boutique Hotel
Our favourite central pick if you want an easy, polished stay in the village. It sits right on Moss Vale Road, across from The Friendly Inn, with spacious rooms arranged around a central courtyard with an on-site restaurant open on weekends.
Berrima
From Sydney: 1 hour and 30 minutes (131 km)
Berrima is one of the oldest towns in the Southern Highlands, with heritage sandstone buildings dating from the 1830s and a relaxed, unhurried village atmosphere. Berrima is cold but quiet in the winter months, with fewer visitors, cosy pub lunches and atmospheric misty mornings.
While most visitors take in on a day trip from nearby Bowral, once the day-trippers have gone, the village is at its most atmospheric, and staying overnight means you can have dinner at Eschalot or a pub lunch at the Surveyor General Inn without needing to drive home afterwards.
OUR FAVOURITE ACCOMMODATION
Oakwood Guesthouse
A stylish, well-appointed one-bedroom guesthouse right in the heart of Berrima village, with a kitchenette, terrace and designer touches throughout. It’s a quiet, peaceful retreat, ideal for couples wanting a comfortable base to explore the Southern Highlands. Almost all accommodation in Berrima is country cottages and houses and this is our favourite for its location and gorgeous style.
Hunter Valley
From Sydney: Around 2 hours (175 km)
The Hunter Valley has over 150 wineries, from $10 cottage tastings to tailored premium experiences with matched food, plus some of Australia’s best Semillon and Shiraz. The restaurant scene runs from hatted fine dining to crispy toasted cheese sandwiches and the restaurants and wineries are open all year, regardless of season.
The Hunter Valley works well as a winter weekend, with enough cosy cellar doors, pubs with open fires and warm restaurants for long lunches to keep you warm, well-fed and sipping a lovely Hunter Valley red all weekend.
READ THE FULL NEXT ESCAPE GUIDE TO HUNTER VALLEY →
OUR FAVOURITE ACCOMMODATION
Hermitage Lodge
Hermitage Lodge is perfect for a winter weekend in the Hunter Valley. The rooms are warm and cosy, with views across the vines and enough room to curl up on the couch with a platter of Hunter Valley cheeses. Plus, Pescara restaurant is on site and only a short walk from the lodges.
Berry
From Sydney: Around 2 hours (154 km)
Berry has excellent cafes, boutique shopping and easy access to both countryside and beaches, with Kiama only a 20-minute drive away if the weather is warm enough for a coastal walk. It’s a good fit for couples looking for a relaxed weekend, or food lovers after quality regional dining.
Winter here means cosy dinners by the fire, rugged-up walks through the boutiques on Queen Street and piping hot donuts from the Berry Donut Van, a local institution since the 1970s.
READ THE FULL NEXT ESCAPE GUIDE TO BERRY →
OUR FAVOURITE ACCOMMODATION
The Mandala Signature Berry
Although there are lovely cottages around Berry (see Stayz if you’d prefer a cottage or house), our pick in winter is the Mandala Signature. It’s a 4 star motel rather than boutique accommodation, but the rooms are warm and cosy and, most importantly, the location is right in the heart of Berry close to all the cafes, boutiques and restaurants.