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, 114 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
The self-contained studio is framed by vibrant red flowers and greenery, featuring large windows that provide natural light. Its modern exterior showcases a combination of corrugated metal and wooden accents, surrounded by the peaceful landscape of native bushland.
Guesthouse in Selby
4.96 out of 5 average rating, 101 reviews

Modern Studio with a View in Selby-Belgrave

Located close to the Belgrave Sth shops, an easy drive to the Dandenongs' top attractions, and situated on 3.5 acres of native bushland and natural granite; this self-contained studio is a perfect base for couples and small families to experience all the hills have to offer. Enjoy the "toots" of Puffing Billy in the distance as you sip on a beverage while overlooking Menzies Creek, or take a walk down our private path to our little rainforest and discover the abundance of native flora and fauna.

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, 387 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, 205 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, 394 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.

Top 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, 438 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.

Top guest favorite
A sleeping area contains a spacious bed with green bedding and pillows. A bedside table is positioned next to the bed, and a woven rug covers the floor. A piece of floral wall art is displayed above the bed, contributing to the room's decor. A light blue door is visible in the background.
Guest suite in Ferntree Gully
4.92 out of 5 average rating, 153 reviews

One bedroom studio apartment in Ferntree Gully

This cosy self contained apartment is located just 5 minutes by car from the iconic 1000 stairs and just a 15 minute walk to ferntree gully train station. New listing with tv, heating and wifi. On street parking. Please note unfortunately we couldn't get more ceiling clearance when we renovated so if you are over 195cms tall this might not be the ideal place for you. Even without ceiling fans! Secure digital door lock with new code generated for each new guest for peace of mind.

Top guest favorite
Place to stay in Cockatoo
5 out of 5 average rating, 43 reviews

Shed4

Shed4, on the north facing hillside of our property in Cockatoo, offers views of natural bush, rural paddocks, and the distant ranges. You may wander and explore or just enjoy the wildlife and birdsongs from the deck or through the bi-fold doors and inside comfort. Shed4 is enhanced by an open fire in cooler weather and a split system air conditioner for the hotter days/nights. A kitchenette of basic facilities and electric BBQ allows for self-catering. Peaceful. Private. Comfy.  

Top guest favorite
A spacious lawn area is surrounded by mature trees, including a large tree in the foreground. White outdoor chairs are arranged under the trees, while a wooden bench sits in the grassy area. The main building is visible, featuring large windows and a covered porch.
Place to stay in Harkaway
4.94 out of 5 average rating, 159 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
4.93 out of 5 average rating, 148 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
4.95 out of 5 average rating, 115 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
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, 193 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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