Vacation rentals in Pakenham Upper

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Top-rated vacation rentals in Pakenham Upper

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Top guest favourite
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 favourite
The exterior of a modern studio is shown, featuring large glass doors that open to the interior. The building is framed by lush greenery, and a wooden deck is adorned with potted plants, creating a welcoming entryway.
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 favourite
A charming shipping container rests among tall eucalyptus trees, featuring a spacious wooden deck with multiple seating areas. The serene outdoor environment is complemented by natural landscaping and steps leading towards the container’s entrance, inviting guests to explore the peaceful surroundings.
Tiny homes 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

Guest favourite
A cozy living space features a round wooden dining table adorned with a vase of dried flowers and fresh fruit. A comfortable seating area includes a charcoal sofa and a decorative wall with patterned tiles. Natural light enters through large windows overlooking a garden, complemented by a wood fireplace.
Guesthouse in Mount Evelyn
4.95 out of 5 average rating, 108 reviews

Country style retreat in Yarra Valley.

Escape to a private retreat in the stunning Yarra Valley! Set on 14 scenic acres, The Stable is a super cozy, self-contained guesthouse, perfectly secluded for total privacy. Just minutes from top Yarra Valley wineries, the Dandenong Ranges, and the Warburton Trail, it’s ideal for a romantic escape or a peaceful country getaway. Unwind in nature, explore nearby attractions, or simply relax in comfort— your perfect retreat awaits in this unforgetable location surrounded with paddocks and nature.

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
4.98 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 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, 393 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 favourite
Apartment in Beaconsfield
4.96 out of 5 average rating, 436 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 favourite
The exterior of a charming house is viewed, featuring a welcoming front porch with railing and steps leading to the entrance. Surrounding greenery and sandy paths contribute to the natural setting, with a gently sloping landscape and distant mountains visible in the background.
Guesthouse in Warburton
4.93 out of 5 average rating, 1,176 reviews

Little House on the Hill

The Little House on the Hill at the eastern end of Warburton overlooks the chooks, the veggie patch, the orchard and across the valley to gorgeous 270° views. It is next door to the Big House, set on an acre that slopes down to the Yarra River. A great swimming spot on hot days and a good way to access the town and the rail trail (five minutes there, maybe ten minutes return - uphill). There are plenty of lovely walks nearby including the Aqueduct Trail that starts further up the hill.

Top guest favourite
Guest suite in Ferntree Gully
4.91 out of 5 average rating, 152 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 favourite
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 favourite
An outdoor fire pit is surrounded by wooden seating, situated on a gravel surface. Soft sunlight filters through surrounding trees, creating a serene atmosphere in the cottage's backyard. The nearby structure features a wooden exterior, complementing the natural surroundings.
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 favourite
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.

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