Holiday houses 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
4.91 out of 5 average rating, 141 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 spacious kitchen area is merged with a living space featuring high ceilings and large windows. A round dining table sits nearby, surrounded by wooden chairs. Comfortable seating areas with plush sofas and armchairs are arranged around a central rug, creating a welcoming atmosphere.
Religious building in Beaconsfield
4.97 out of 5 average rating, 299 reviews

The Chapel, 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 15 min walk, Monash Fwy close by) is ideally located on the gateway to Gippsland. This open aired chapel added to the main homestead 100 years ago, is attached to the main house. A beautiful relaxing space, which has its own private entry and is locked separately from the main house. Situated on a rise, in a quiet court with open garden views. Parking available.

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, 224 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, 412 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 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, 142 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
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, 356 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 favourite
An off-grid tiny house is set against a backdrop of tall trees, with a wooden deck extending toward a grassy area. A fire pit is positioned nearby, surrounded by two chairs. Soft evening light highlights the exterior and landscape.
Tiny home in Three Bridges
4.93 out of 5 average rating, 136 reviews

Wombat Rest Tiny House

Welcome to Wombat Rest, a cosy off-grid tiny house nestled on an acre block in a quiet residential street of the Yarra Valley. Located 15 minutes from Warburton, this little gem is the perfect spot for retreating to the peace of the bush, only a short drive from beautiful Yarra Valley wineries. Our guests love relaxing in the hammock on the deck, listening to the birdsong, and snuggling up around an open fire. We can’t wait to welcome you to our forest retreat!

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, 199 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 stylish cabin entrance features a glass door framed by warm wooden panels. Soft curtains are drawn open, revealing a glimpse of an inviting bedroom with neutral tones. Warm lights illuminate the exterior, creating an inviting ambiance.
Tiny home in Kallista
4.94 out of 5 average rating, 332 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 deep soaking tub is situated beside large bifold windows, which open to reveal a serene view of towering trees and lush greenery. A wooden tray rests on the tub's edge, featuring a decorative bottle and a soft towel, providing a calming atmosphere.
Cabin in Gembrook
5 out of 5 average rating, 299 reviews

Secluded Cabin in the Woods Andersons Eco Retreat

Anderson’s Eco Retreat, Off grid Cabin in the Woods. A slow stay for adults only. Wrap yourself in nature! Towering trees, bird songs, the fresh forest breeze. Private & secluded. Take a dip in the spring fed swimming hole. Submerge into a deep soaking tub surrounded by windows & trees. Curl up in front of the warm crackling wood fire with your special someone. A peaceful sanctuary for those looking to detox from life for a while.

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.
Apartment in Gembrook
4.96 out of 5 average rating, 142 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.

Top Guest favourite
Cottage in Gembrook
4.92 out of 5 average rating, 106 reviews

BB's Bungalow

Nestled in the hills where cows roam, trees soar and birds are plentiful. Forget your worries in beautiful, relaxing Gembrook. Escape and recharge at BB's Bungalow for the weekend or longer. Close to wineries, fields, berry farms and the Puffing Billy Railway. Only 2km to the township of Gembrook which is walkable but best travelled to by car.

Popular amenities for Pakenham Upper holiday rentals

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