Holiday rentals in Pakenham Upper

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Top-rated holiday rentals in Pakenham Upper

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Cottage in Cockatoo
4.92 out of 5 average rating, 146 reviews

Laughing Kookaburra Cottage | surrounded by nature

Take a break and soak up the beauty of the Dandenong Ranges and Yarra Valley in our cosy cottage. With two queen bedrooms, a full kitchen and plenty of parking, it’s an easy place to unwind. Wander nearby forest trails, ride Puffing Billy, visit cellar doors or enjoy good local food and coffee. Or stay in, put on some music, and relax on the verandah while kookaburras, parrots, echidnas and wombats wander by. Right next door to Avalon Castle and an easy walk to Chae. Linen and towels provided.

Top guest favourite
A wooden deck features comfortable wicker seating with light-colored cushions, inviting relaxation. A small table complements the seating area, with a clay vase positioned in the foreground. Lush greenery surrounds the deck, providing serene mountain views extending to the distant landscape.
Cottage in Menzies Creek
4.97 out of 5 average rating, 229 reviews

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.

Top guest favourite
The retreat is nestled beneath a large tree, illuminated softly by outdoor lighting at dusk. The brick structure features large windows that allow warm light to emanate from within. Surrounding greenery and a stone pathway contribute to the serene outdoor environment.
Cottage in Macclesfield
4.99 out of 5 average rating, 424 reviews

Writer's Block is a peaceful and romantic retreat

Writer’s Block retreat is the perfect romantic getaway for couples and creatives. 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-min drive to local wineries & markets. Fully functional kitchen & laundry. With a spectacular outdoor bath.

Guest favourite
The entrance of Sunrise Cottage is framed by vibrant white flowers and lush greenery. Potted plants and a decorative urn are positioned near the doorway, while a cozy seating area is visible through the window, inviting leisurely moments in a tranquil setting.
Cottage in Kallista
4.92 out of 5 average rating, 358 reviews

Sunrise Cottage (at Mont du Soleil Estate)

Sunrise Cottage part of the 'Mont du Soleil' Estate, located in Emerald on 40 acres, in the heart of the beautiful Dandenongs. A truly unique property inspired by the buildings & grounds of Provence & Tuscany. You’ll love the unique design & ambience of the property, the stunning views, peace and tranquility; yet less than an hour by car from Melbourne CBD. Featured on Neighbours Xmas special December 2024. Note: We host photo shoots on the property but NOT in the Cottage.

Top guest favourite
Farm stay in Wandin North
4.99 out of 5 average rating, 432 reviews

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.

Guest favourite
A rustic doorway framed by natural stone greets visitors. A welcome mat is placed at the entrance, leading into a warm interior visible through the open door. Wooden chairs and a dining area are subtly hinted at inside, with natural light illuminating the space.
Barn in Gembrook
4.91 out of 5 average rating, 149 reviews

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.

Top guest favourite
An exterior view of the cottage displays a vibrant yellow door framed by a cozy seating area featuring a small round table and two chairs. Potted plants provide greenery, while a wooden deck adds texture to the entrance. Soft light glows through the nearby window.
Guest house in Emerald
4.98 out of 5 average rating, 109 reviews

Clematis View Cottage

Take it easy at this unique and tranquil getaway. Clematis View Cottage is detached studio/apartment within the grounds of an old Dandenongs farmhouse set on over an acre of botanical gardens. The Paradise Valley Hotel offers great dining, a 5 minute walk from the studio and views to Port Phillip Bay at sunset offer a perfect end to your day. Clematis View Cottage is a wonderful base for popular tourist destinations in The Dandenongs or Yarra Valley

Guest favourite
A full-size converted bus is parked on a grassy area, surrounded by native trees. The exterior features a faded blue and orange color scheme, with the words 'I BOUGHT A BUS' prominently displayed on the front. Bright sunlight illuminates the scene, contributing to a cheerful atmosphere.
Home in Pakenham Upper
4.92 out of 5 average rating, 202 reviews

Bus in Toomuc Valley

Full size Sydney yellow bus converted in style. A comfortable bed, with self contained kitchen, refrigerator, TV, couch, laundry, and. great for horse enthusiasts. Small paddock beside bus for your horse. Ride through to Chambers Reserve and the many horse trails. Enjoy farm life, complete with baby wombats to feed. Every cent of funds go to the wildlife Shelter. Peaceful bush surrounds, perfect for artists, nature lovers, and good old relaxing.

Top guest favourite
The exterior of the modern cabin features corrugated black siding and a covered porch area. An outdoor bathtub sits elegantly on the porch, alongside a small table. Soft lighting illuminates the space, framed by surrounding trees and natural foliage.
Tiny home in Kallista
4.94 out of 5 average rating, 341 reviews

The Cabin farm stay in Emerald Alkira Glamping

OUTDOOR BATH BLISS! Dreaming of the perfect weekend escape? This stunning, modern cabin is the kind of place that steals your heart the moment you arrive. Sink into your outdoor bath under the stars, surrounded by mountain air and serenity. With stylish interiors, a fully equipped outdoor kitchen, a separate shower and bathroom area, and friendly animals, it’s the ultimate cozy retreat, just an hour from Melbourne CBD. An unforgettable getaway!

Top guest favourite
A cozy tiny house is situated on a gentle hill, surrounded by lush greenery. The structure features a covered outdoor deck and large windows reflecting natural light. Nearby trees provide a serene backdrop, enhancing the sense of tranquility in the landscape.
Tiny home in Beaconsfield Upper
4.9 out of 5 average rating, 125 reviews

Escape to a Haven in the Hills

Jabulani Getaway is a beautiful Tiny House that is situated on a stunning equestrian property in the foothills of the Dandenong Ranges. Combining luxury and comfort this little oasis on the fringe of Melbourne offers the experience of connecting with nature while being only 10 minutes from restaurants and tourist attractions. Relax at sunset on the deck, overlooking our resident kangaroos, wallabies, and beautiful horses grazing peacefully.

Top guest favourite
A spacious bedroom features a comfortable bed dressed in crisp linens. Two nightstands with lamps flank the bed, while a decorative throw adds texture. Natural light filters through a large window, enhancing the serene atmosphere created by greenery visible outside.
Home in Sherbrooke
4.9 out of 5 average rating, 259 reviews

Position Perfect! In the heart of Sherbrooke

Less than an hours drive from Melbourne CBD, situated in heart of Sherbrooke, this Eco accommodation is perfect for your next weekend or mid week get away. We are located just a short stroll to Burnham Beeches, Alfred Nicolas Gardens, Poets Lane, Woods Cafe, Marybrook Manor and Sherbrooke Falls. Perfect for two couples, this immaculate light and spacious fully self contained recently renovated 2 bedroom home.

Top guest favourite
A bright lounge area is equipped with a comfortable light-colored sofa, an ottoman, and an armchair. Large glass doors provide access to the balcony, while a modern TV sits on a white media unit. Decorative elements include a display cabinet and a potted plant.
Flat in Gembrook
4.97 out of 5 average rating, 146 reviews

The Snow Globe Suite - Scrumptious Couples Retreat

The Snow Globe Suite is a gorgeous, modern, light and airy one bedroom apartment situated in the very heart of Gembrook. A romantic stay for two at the Snow Globe Suite places you within a minute's walk to outstanding cafes and restaurants, Puffing Billy at Gembrook Station, beautiful forest walks and a stunning apartment view of the Warburton Ranges.

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