Family-friendly holiday rentals in Pakenham

Jacky Winter Gardens - Modern, Artistic Cabin Close to Creek

Recharge by the open fireplace of this beautiful cabin, sequestered in the Dandenong Ranges. Rustic on the outside, modern on the inside, this serene space inspires relaxation in proximity to wild nature, far from the stresses of daily life. Designed by interior architects Hearth Studio, Jacky Winter Gardens brings together the calming waters of Clematis Creek, the rich soil of the gardens, the pure air of the Dandenong Ranges and every modern convenience you can imagine to give you a wholly satisfying holiday experience. Our mission is to offer private and secluded luxury accommodation for visitors to the hills, including singles, couples and small groups, as well as showcase the work of our artists and incorporate it into the day-to-day life of the house. Through our monthly artist-in-residence program we also support other commercial artists working in any discipline. We’ve feathered our nest with work from some of The Jacky Winter Group’s world-renowned stable of artists. From custom-made glasswork and wallpaper, to games and framed prints, you’ll become acquainted with new artists, or perhaps be reunited with some you already know. The beautiful Clematis Creek meanders along the bottom of the gardens, and its cheerful burbling is the aural backdrop to your stay. If you want to get closer to the water there is easy and safe access down to the creekbank, which makes it the ideal spot for meditation or private reflection. Located just 45-minutes from Melbourne by car, and situated within walking distance to the town centre with its wonderful Cameo Cinemas, Jacky Winter Gardens straddles the two worlds of nature and civilisation, achieving a perfect holiday balance for solo travellers, couples and small groups. You can find more information and photos of the property online at our dedicated property site which isn't difficult to find ;) During their stay, guests have private and exclusive access to the entire house, gardens, and studio. None, but available on phone, email, and in person (when possible) to answer any questions! The house is a luxury creative retreat set amidst a half-acre of stunning flora, a creek, and natural bushland. The wild yet tranquil beauty of the Dandenong Ranges has attracted artists to the area for more than a century. Jacky Winter Gardens is situated in Belgrave, Victoria, a short walk from the train station and centre of town. Full directions will be provided upon booking. Car – Belgrave is a 45-minute drive from Melbourne. Train – From Flinders Street Station, catch the Belgrave train to Belgrave Station (it takes just over an hour). Jacky Winter Gardens is a ten-minute walk along a paved walkway from the train station. Jacky Winter Gardens is the perfect retreat for solo travellers or couples, but we are able to accommodate up to five guests: two in the master bedroom, two in the living room on the double-bed fold-out sofa, and one in the studio on a single sofa bed. Jacky Winter Gardens is now dog and child friendly. We also accept single night bookings when available. ***Please message us if you wish to bring your pet or want to stay for a single night before booking*** Each additional guest (beyond the first two) will incur a tariff of 25.00 per night. Unfortunately, due to site limitations, there is no wheelchair access at this time. Due to our location in a high fire risk area, we also have detailed Fire Safety policies which are outlined on our website, which once again is not hard to find.

Stylish unit with all the comforts of home

✨⭐️ Welcome to Pakenham ⭐️✨ Designed for families, friends, or small groups, our 2-bedroom unit offers all the comforts and conveniences of a real home, perfect for both short stays and extended visits. Nearby attractions include Gumbuya World (15 min) and Puffing Billy Railway (25 min) — ideal for family outings. You’ll also find the Mornington Peninsula, Yarra Valley, Phillip Island, and Melbourne CBD all within an hour’s drive — perfect for day trips if you need ideas to fill your calendar.

Vintage Caravan, Rainforest & Lyrebirds

Our 1959-vintage caravan is just 12ft long, best for a couple or two friends. At a pinch, two children could sleep in the king single bed; see the photos and description further down. Wake up to the sounds of Lyrebirds, enjoy a private walk in our rainforest gully and stroll around the garden, one of the best private gardens in the Dandenongs. Offering a minimum one-night stay for a quick getaway, or stay longer & enjoy the peace, sit by the fire - made from a beer keg, and roast marshmallows.

Menzies Cottage

Menzies Cottage is an hour east of Melbourne & set high on a mountain-side in the beautiful Dandenong Ranges. Enjoy views out to the Wellington Road farmlands & Cardinia Reservoir. On a clear day you can see Arthur’s Seat, Port Phillip & Westernport Bays. Visit nearby Puffing Billy Steam Train, go bushwalking, feed the friendly farm animals or settle-in for a lazy afternoon before watching the sun set. The cottage is fully self contained & with your own private entrance, deck & enclosed garden.

Writer's Block is a peaceful and romantic retreat

Writer’s Block retreat is the perfect romantic getaway for couples or writers and artists. It was selected as 1 of 11 finalists in the 2022 Airbnb Best Nature Stay for Aus & NZ. Set on 27 acres and surrounded by gums and chestnut trees, this private rural retreat is within a 10-minute drive to cafes, restaurants, shops, picturesque walks and the famous Puffing Billy. The Yarra Valley is only a 30-minute scenic drive to local wineries and farmers' markets. Fully functional kitchen and laundry.

The loft, Villa Maria Circa 1890 Eco Friendly

Villa Maria Beaconsfield Circa 1890 This charming old homestead and country chapel, 100 metres from the Old Princess Hwy (train station 13 min walk, Monash Fwy close by) is ideally located on the gateway to Gippsland. This open aired apartment is craftsman built, detailed and has architectural shaped ceilings. A beautiful relaxing space, which has its own parking, private entry foyer and is locked separately form the main house. Situated on a rise, in a quiet court with open undulating views.

Modern Townhouse in Eden Rise Berwick opp Park

This townhouse is perfect for small families or couples, in a peaceful, leafy location opposite a park, ideal for walks & picnics. Car not needed, as shopping mall 'Eden Rise' is next door and Zagames including MPD steak kitchen is walking distance away. If you do have a car, a fully enclosed & secure 2 car garage is available. The house is close to hospitals such as Casey & St John of God and close to Berwick Village where there's great restaurants, boutiques & Botanical Gardens to explore.

Duck'n Hill Barn (& EV charge station!)

Watch miniature highlands, geese on the dams & stunning sunsets across city views from rocking chairs on The Barn's private deck. Perfect for romantic getaways, family retreats, micro weddings & bridal parties. Whatever the agenda you won't want to leave! A fabulous location within minutes drive to ideal Yarra Valley attractions such as the Yarra Valley Chocolaterie, Yarra Valley Dairy, Panton Hill Hotel, Coldstream Brewery, Rochford, Healesville Sanctuary & Four Pillars Gin Distillery.

Country Vineyard Escape/Fire Pit/Sleeps 12

The perfect country escape for wedding prep, group getaways and winery weekends. Sleeps up to 12 next door to Cannibal Creek Vineyard with direct access, and just 7km from Gumbuya World. Gather around the outdoor fire pit, enjoy long lunches on the verandah overlooking established gardens, and wake up to peaceful rural views — all just 2.5km from the M1 for an easy drive from Melbourne. The home has 4 bedrooms (4th doubles as 2nd living) 2 beautiful bathrooms plus a third toilet.

CHERRY ORCHARD CABIN - Yarra Valley FARM STAY

Nestled on a 30-acre working fig and finger lime orchard in the Yarra Valley, Cherry Orchard Cabin offers a peaceful retreat with fresh air and sweeping hill views. Just an hour from Melbourne, it’s perfect for exploring nearby wineries, many just a short drive away, and 2.5 km from the Warburton Rail Trail. The iconic Puffing Billy Railway and Healesville Sanctuary are also nearby, making it an ideal spot for nature lovers and those seeking a blend of relaxation and adventure.

The Poplars Farm Stay

Escape the city's hustle and bustle and unwind among wildlife and magnificent rural scenery. The Poplars is a beautifully restored 1930s pioneers’ cottage, set on a private farm with acres of serene gardens, towering Manna Gums, and abundant wildlife! From the moment you arrive, let your holiday begin effortlessly with one of our locally curated hampers—designed to help you settle in quickly, indulge in a gourmet breakfast, or celebrate a special occasion in style!

Barn with free Breakfast

Nestled on 10 acres in Gembrook, this private barn is spacious & exudes rustic charm. Within an hour's drive of Melbourne, you'll stay amongst gums where the birdsong is often the only sounds you'll hear. Native wildlife is abundant and often passing through. The township of Gembrook is only a 5 minute drive & boasts fine dining at the Independent, cafes, and more. Puffing Billy is a regular visitor to the railway station. Free cooked breakfast inc in your stay.