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, 149 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
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, 427 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.

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, 234 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.

Guest favourite
A wooden deck features a long table with seating, illuminated by string lights above. Views of surrounding trees provide a natural backdrop, while a cozy sleeping area can be seen through glass doors, enhancing the connection between indoor and outdoor spaces.
Tiny home in Gruyere
4.93 out of 5 average rating, 346 reviews

Wanderlust - I want something just like this

When you yearn for seclusion hidden away amidst nature, be lead down a path where at first you can barely see anything. Come further and the wonders start to reveal themselves. With each step you’ll leave the world further behind, a smile will brake out, and the peace that is wanderlust will consume you. Then you’ll reach your sanctuary, private, secluded, immersed in the sounds of nature and surrounded by jaw dropping views. It’s then you’ll say to yourself - I want something just like this.

Top guest favourite
A private outdoor spa bath is surrounded by lush bamboo and tropical plants. Soft bubbles gently rise in the water, while candles are placed on natural stone and wooden surfaces. A stylish seating area with plush cushions and a modern, tall planter complete the tranquil setting.
Flat in Mornington
4.96 out of 5 average rating, 699 reviews

Tantilize: Luxury Romantic Retreat

Snuggle up in luxury! At Tantilize we go over and above to help you spoil your someone special. Tantilize caters for wedding nights, birthdays, anniversaries, and other special occasions. Whether you are just enjoying pampering time together, or granting your loved one a memorable gift stay for 1 or more nights, Tantilize will not disappoint! We regularly receive compliments on our special touches and attention to detail to make sure your stay is an experience you will both never forget.

Top guest favourite
A spacious sleeping area features a king bed with neutral bedding and accent pillows. A comfortable sofa is positioned near a round coffee table, adorned with snacks and a small plant. Large windows provide natural light, enhancing the room's modern decor.
Flat in Sassafras
4.99 out of 5 average rating, 113 reviews

'The Sett'. Your private luxury mountain retreat.

The Sett Finalist for Airbnb’s Best New Host 2025 award, The Sett is a private couples’ retreat in the Dandenong Ranges. Enjoy your own private entrance, a cosy gas fire, a luxury bathroom, and a welcoming space with large windows that frame the forest surrounds. Thoughtful touches make every stay special., including a delicious continental breakfast. To keep the retreat calm & carefree, The Sett does not include full cooking facilities. A kettle, coffee machine, and toaster are provided.

Top guest favourite
The Barn presents a modern white exterior with a spacious roof, complemented by large feature doors. Gentle hills and muted clouds form the backdrop, enhancing the rural landscape. Surrounding greenery and pathways add to the welcoming ambiance of the property.
Barn in Epping
4.98 out of 5 average rating, 275 reviews

The Barn - Yarra Valley Bridal Accommodation

Designed for unforgettable wedding mornings and luxurious country escapes, The Barn is set on 10 acres in the heart of the Yarra Valley. Surrounded by rolling mountain views, this beautifully transformed barn offers a peaceful setting, just minutes from many of the region’s most sought-after wedding venues and wineries. Whether you’re celebrating your wedding day, an anniversary, planning a surprise proposal or enjoying a relaxing getaway, The Barn is a boutique stay unlike anywhere else.

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
4.91 out of 5 average rating, 362 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.

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, 150 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.

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
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
4.91 out of 5 average rating, 127 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 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, 148 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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