Vacation rentals in Pakenham Upper

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Top-rated vacation rentals in Pakenham Upper

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Top guest favorite
A spacious bed with crisp white linens is adorned with two decorative yellow cushions. Framed abstract art pieces hang above the headboard, while small potted plants and illuminated branches flank the bed, adding a gentle touch of warmth to the ambiance.
Home in Pakenham
4.91 out of 5 average rating, 106 reviews

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.

Top guest favorite
A rustic metal sculpture of a bird stands in the foreground, surrounded by green vegetation. In the background, a charming shipping container home is visible with large windows and a spacious deck, overlooking a serene small dam sprinkled with lily pads.
Tiny home in Clematis
4.91 out of 5 average rating, 382 reviews

Tiny Home Farm Stay Converted Cosy Container

Have your own unique tiny home experience in this converted shipping container with large decking and outdoor area 2 night min stay weekends (Fri to Sun) Available 7 days a week Located in the foothills of the Dandenong ranges, close to many tourist attractions including Puffing Billy The site is shared with the owners dwelling, but you will still get the spacious feel as the 2 dwellings are set far apart Nestled on a 6.5 acre farm that houses an array of friendly farm animals No Children Policy

Top guest favorite
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
4.98 out of 5 average rating, 196 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 favorite
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, 383 reviews

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.

Guest favorite
A bright entrance leads into a spacious living area furnished with blue sofas. Natural light streams through a doorway into a bedroom area, where a soft bed with patterned bedding is visible. Light wooden flooring extends throughout the clean, modern space.
Apartment in Beaconsfield
4.96 out of 5 average rating, 428 reviews

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.

Guest favorite
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 Emerald
4.93 out of 5 average rating, 290 reviews

The Cabin farm stay in Emerald Alkira Glamping

OUTDOOR BATH BLISS! Dreaming of the perfect weekend escape? This stunning, modern cabin (ranked #2 on Airbnb’s most wish-listed stays!) 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 favorite
The living room features a classic fireplace surrounded by a stylish mantle and is warmed by a glowing fire. Large windows offer views of the garden, while plants adorn the space. Comfortable seating is complemented by a wooden coffee table and decorative rug.
Cottage in The Patch
4.94 out of 5 average rating, 121 reviews

The Artisan’s Cottage The Patch, Dandenong Ranges

Situated in the beautiful Dandenong Ranges, a one hour drive from Melbourne's CBD, The Artisan’s Cottage is a truly unique place to unwind. Set in almost one acre of rambling gardens, the cottage features a spacious bedroom with a queen sized bed, a beautifully appointed ensuite, a large living/dining room warmed by a wood fire and a well equipped kitchenette. The Artisan's Cottage is home to Penny Olive Sourdough bakery and Tiny Block Wine, run by your hosts Penny and Andrew.

Top guest favorite
A cozy suite is displayed featuring a queen size bed with a textured blanket. A sitting area includes two chairs beside a small round table, surrounded by warm-colored walls. The kitchenette is visible in the background, equipped with essential appliances and illuminated by natural light.
Place to stay in Harkaway
4.94 out of 5 average rating, 152 reviews

The Workshop @ Kilfera

Looking for a weekend getaway or simply a place to lay your head after a busy day of catching up with family and friends? Come and stay at the Workshop@Kilfera on the fringe of Melbourne. A fun, unique and quirky suite for two on a private property in beautiful Harkaway, only minutes from restaurants and tourist attractions. Enjoy the peaceful setting surrounded by gorgeous nature. Listen to the birds chirping and the rustling of wind through the 100 year old Cypress trees.

Guest favorite
A cozy outdoor seating area features two wooden chairs and a fire pit surrounded by gravel. The cottage's rustic exterior, composed of light green and pale wood siding, is visible in the background, framed by lush greenery and sunlight filtering through the trees.
Home in Guys Hill
4.92 out of 5 average rating, 144 reviews

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!

Top guest favorite
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
4.94 out of 5 average rating, 108 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 favorite
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 Emerald
4.92 out of 5 average rating, 342 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 photoshoots but not in the Cottage.

Guest favorite
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
4.91 out of 5 average rating, 188 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.

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