
House holiday rentals in Cheltenham
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Top-rated house rentals in Cheltenham
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Jacky Winter Gardens - Modern, Artistic Cabin Close to Creek
Recharge by the open fireplace of this beautiful cabin, sequestered in the Dandenong Ranges. Rustic on the outside, modern on the inside, this serene space inspires relaxation in proximity to wild nature, far from the stresses of daily life. Designed by interior architects Hearth Studio, Jacky Winter Gardens brings together the calming waters of Clematis Creek, the rich soil of the gardens, the pure air of the Dandenong Ranges and every modern convenience you can imagine to give you a wholly satisfying holiday experience. Our mission is to offer private and secluded luxury accommodation for visitors to the hills, including singles, couples and small groups, as well as showcase the work of our artists and incorporate it into the day-to-day life of the house. Through our monthly artist-in-residence program we also support other commercial artists working in any discipline. We’ve feathered our nest with work from some of The Jacky Winter Group’s world-renowned stable of artists. From custom-made glasswork and wallpaper, to games and framed prints, you’ll become acquainted with new artists, or perhaps be reunited with some you already know. The beautiful Clematis Creek meanders along the bottom of the gardens, and its cheerful burbling is the aural backdrop to your stay. If you want to get closer to the water there is easy and safe access down to the creekbank, which makes it the ideal spot for meditation or private reflection. Located just 45-minutes from Melbourne by car, and situated within walking distance to the town centre with its wonderful Cameo Cinemas, Jacky Winter Gardens straddles the two worlds of nature and civilisation, achieving a perfect holiday balance for solo travellers, couples and small groups. You can find more information and photos of the property online at our dedicated property site which isn't difficult to find ;) During their stay, guests have private and exclusive access to the entire house, gardens, and studio. None, but available on phone, email, and in person (when possible) to answer any questions! The house is a luxury creative retreat set amidst a half-acre of stunning flora, a creek, and natural bushland. The wild yet tranquil beauty of the Dandenong Ranges has attracted artists to the area for more than a century. Jacky Winter Gardens is situated in Belgrave, Victoria, a short walk from the train station and centre of town. Full directions will be provided upon booking. Car – Belgrave is a 45-minute drive from Melbourne. Train – From Flinders Street Station, catch the Belgrave train to Belgrave Station (it takes just over an hour). Jacky Winter Gardens is a ten-minute walk along a paved walkway from the train station. Jacky Winter Gardens is the perfect retreat for solo travellers or couples, but we are able to accommodate up to five guests: two in the master bedroom, two in the living room on the double-bed fold-out sofa, and one in the studio on a single sofa bed. Jacky Winter Gardens is now dog and child friendly. We also accept single night bookings when available. ***Please message us if you wish to bring your pet or want to stay for a single night before booking*** Each additional guest (beyond the first two) will incur a tariff of 25.00 per night. Unfortunately, due to site limitations, there is no wheelchair access at this time. Due to our location in a high fire risk area, we also have detailed Fire Safety policies which are outlined on our website, which once again is not hard to find.

Beachside retreat
This 3-bedroom family home is perfectly located in the bayside suburb of Aspendale, Melbourne. Short walk to Aspendale Beach, and Mordialloc Pier, you will enjoy the ocean and the white sands of the bay and the local shopping district. As it is a quiet neighborhood, we have a no-party policy. Three bedroom, 2 queen & 1 trundle Off-road carport Free Wifi, Netflix, Microwave, Fridge, Stove and oven, Dishwasher Cookware and Dinnerware Pillows, Quilts, blankets Modern Laundry Private backyard

Space design luxury. Zinc house - urban oasis
Private and spacious ultra modern 2 Storey townhouse, minutes walk from the Windsor restaurants and cafes in Chapel Street. Relax on the big red couches surrounded by the art and music. Fully equipped kitchen. Classic Victorian dining table. Bedrooms boasting space, big comfy mattresses, quality linen, and fluffy doonas. Private courtyard. Easy parking. Easy access. Perfect living. Your host is the owner. Whether for pleasure, business or visiting friends the ultimate Windsor abode.

Quiet Designer Home steps from High St & Hawksburn
Woodfull House is a an immaculate, luxury three bedroom house located in peaceful street and ideally situated on the green fringe between the happening Prahran/South Yarra precinct and Toorak/Armadale. Enjoy morning coffee in the private designer garden, cook in the fully equipped kitchen, and relax by the fireplace after exploring Melbourne. Unlike some inner-city stays, natural light fills every room. Generous living spaces and outdoor garden — ideal for families, friends or longer stays.

Sherlock's Home - Magical Richmond Warehouse
Sherlock’s Home, a one-of-a-kind 1850s Cordial Factory warehouse conversion in the best part of Richmond (as featured on Broadsheet). Architecturally-designed to maximise openness, our bespoke house is over 4 levels, with 2 bedrooms (Master with king bed & ensuite), 2 lounge areas, single garage, & shaded northern patio. Our exclusive Melbourne location is unbeatable: - 100m to Church St - 200m to Bridge Rd - 750m to Swan St - 1.9km to Sports Precinct (MCG, Rod Laver Arena, AAMI Park)

"Yering Park Cottage"
"Yering Park Cottage" is set in a private garden setting on 1/2 acre of landscaped gardens with beautiful rural and mountain views at the gateway to the Yarra Valley, only minutes from Coombe-The Melba Estate, Stones, Meletos, Yering Station, wineries and other attractions such as world class golf courses, restaurants, Healesville Sanctuary and township. Fully renovated offering excellent accommodation for up to 6 guests, large living/kitchen/dining area, separate toilet and laundry

Beautifully curated 2 bedroom home
This 100 year old workers cottage is all about bespoke interiors The walls and shelves filled with gorgeous art work, the home has specially sourced vintage pieces scattered everywhere, the beds are filled with luxurious linens and the lounge has a 3 seater couch you may never want to get up from. Centrally located, across the road from the South Melbourne Markets, walking distance to the Albert Park Lake and a quick tram trip to the CBD. Please note- no TV, so bring devices if needed.

‘The bayside’ 6BR Beautifully brand new house
This luxury house was built in 2023 with 6 bedrooms, 4 bathrooms, spacious kitchen, private backyard and double garage. All appliances are brand new. It contains central air-condition heating & cooling. Baby friendly with chair, cot and change table. Enjoy your second home away from home. 1 minute walk to Thrift Park Shopping Centre (Woolworths, Pharmacy, Café, Restaurants, etc) 2 minutes drive to train station 3 minutes to beach STRICTLY NO PARTIES NO PETS ALLOWED NO SMOKING INDOORS

Inviting light filled home with cozy fireplace
Welcome to Casa on Clyde, our beautiful 1870's period home in the heart of St Kilda. Enjoy the light filled spaces, sitting in front of the cosy fireplace or star gazing via the skylights whilst lying in bed. Walking distance to cafes, restaurants, theatres, nightlife, Sunday markets, beaches and all the other eclectic attractions St Kilda is famous for. Trams are located at the end of the street for easy access into any other pocket of Melbourne.

Charming Victorian Getaway with Outside Images
This beautifully renovated Victorian terrace is bright clean and welcoming with all the modern comforts. It is in the heart of Elsternwick in a quiet tree lined street. Only a 1-2 minute walk to Cafe’s , restaurants and shops. Public Transport is very close with the tram about a 2 minute walk or the train an 8 minute walk. By train you will be in the city centre in 16 minutes. Two $12 Myki(public transport cards) are also provided for your use.

Spacious and cozy 3 bedroom home
Welcome to our spacious and cozy family home with WiFi. Easy access to transportation and neighbourhood. There are many fantastic cafes, restaurants, fast food, bakeries around. Plus! There are many supermarkets and shopping centres like DFO, Costco, Westfield Southland are all within a few minutes drive away. The nearest beach is about a 4-minute drive. Ideal for holidays, business trips, and families for long and short term temporary stays.

No.63 on Brunswick St Fitzroy
The city is on your doorstep. Steps away from Gertrude St, a 10 minute walk from Smith St and a 15 minute walk to the MCG. Located above a design studio the space is curated for an exceptional stay. A modern take on heritage interiors. The large living & dining has a kitchen with cooking facilities. Large comfortable bedrooms face towards the rear of the property A courtyard has dining furniture
Popular amenities for house rentals in Cheltenham
House rentals with a pool

4 Bedroom Home in the foot of Yarra Ranges

4 Bedroom Home with Pool Aircon WIFI
///ARCHITECTURAL HOME / BEACH /CBD / CAFE PRECINCT

Family Cityside Beach House, Pool & Roof Terrace

Yarra Valley Serenity House in Golf Country Club

Hampton’s Hidden Gem, Pool, Beaches, Entire home.

Tanglewood

Bella Vista Mornington Esplanade
Weekly house rentals

Fun-Filled Beach Retreat for up to 8 people

Glorius Aspendale beach house

The Beach House: Waterfront with Boat Mooring

Parkdale Beach + Village base

Hampton Haven: Spacious Bayside Home

Cozy 2BR Unit Near Beach and Shops in Mentone

Gerty Longroom: Rooftop onsen & fresh produce

Private cottage in 1/2acre forest Dandenong Ranges
Private house rentals

The Black Cockatoo

A Sylvia Home in Deepdene

Bushland Getaway

Elegant Caulfield North Family Home

House of Windsor

Brilliant Bungalow Home at Oakleigh and Chadstone

Welcome to Chakra, A warm and peaceful home

Country Style 2 bedroom House - Off Street Parking
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $139 SGD | $84 SGD | $118 SGD | $219 SGD | $100 SGD | $103 SGD | $130 SGD | $142 SGD | $158 SGD | $118 SGD | $156 SGD | $130 SGD |
| Avg. temp | 20°C | 20°C | 19°C | 15°C | 13°C | 11°C | 10°C | 11°C | 13°C | 14°C | 17°C | 18°C |
Quick stats about house rentals in Cheltenham

Total holiday rentals
Explore 60 holiday rentals in Cheltenham

Nightly prices starting at
Cheltenham holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 610 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Cheltenham holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Cheltenham rentals

4.8 Average rating
Cheltenham stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
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- Brunswick Street
- Phillip Island
- Melbourne Central
- Crown Melbourne
- Melbourne Convention and Exhibition Centre
- Marvel Stadium
- St Kilda beach
- Rod Laver Arena
- Sorrento Beach
- Peninsula Hot Springs
- Melbourne Cricket Ground
- Queen Victoria Market
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- West Richmond Station





