
House holiday rentals in Cheltenham
Find and book unique houses on Airbnb
Top-rated house rentals in Cheltenham
Guests agree: these houses are highly rated for location, cleanliness and more.

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

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.

Cosy Seaside Retreat - Charming Unit by the Beach
Discover a charming retreat just 2km from Mentone's pristine beaches. This cosy 2-storey unit boasts a fully equipped kitchen, offering a perfect blend of comfort and convenience. Immerse yourself in a relaxing getaway, surrounded by the best south-east Melbourne has to offer! Local shops, restaurants and public transportation within walking distance and a mere 35 minutes from the Melbourne CBD. This location is a great central base for anyone wanting to explore the south-east of Victoria.

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)

Highett Charm - Spacious modern 3 bedroom Unit
This 3 bedroom unit is spacious enough for a family or cosy enough for a couple. It is a short walk to the center of Highett and train station. Southland Shopping Centre is only a 3min drive away for all of your shopping needs. A spacious undercover outdoor space offers guests the opportunity to cook up a storm on the BBQ provided. Ducted heating and reverse cycle cooling for your comfort. Smart TV's are installed in all rooms. 1 undercover and one additional car space is available.

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

Large Bayside Home
Nestled in the heart of Beaumaris, this spacious 3-bedroom, 2-bathroom home is ideal for both short and long-term stays. Situated on a peaceful street with off-street parking, discounts of 10% are available for stays of 1 month or more. Conveniently close to shops, cafes, and bus stops, the home is just a short walk from Beaumaris Secondary College. It’s also within the coveted Mentone Girls’ Secondary College zone, top-rated primary schools, and only minutes from the bay.

Mordi Beach House Getaway
Enjoy the crisp sea breeze and sunshine in our bright, contemporary beach house. It’s your perfect blend of relaxation and style. • Open-plan living • Spacious bedrooms with plush bedding • Outdoor living&BBQ equipment • Fully equipped kitchen • Onsite restaurant Whether you’re here for a romantic escape, a family holiday, or a weekend with friends, our beach house offers the perfect mix of relaxation and indulgence. Enjoy morning walks by the creek and sea.

The Gables 2
The Gables is a gracious old house on three beautiful acres in Belgrave, close to wedding venues, national park, Trees adventure and Puffing Billy. We do not allow events at all, but we have many brides who stay with their bridesmaids on the eve of their wedding and have beautiful pre-wedding photos taken here. We are limited in parking to only 5 cars. There is a bathroom for each double room. Please be aware that we live on the property in the cottage next door.

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.
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

Tranquil Estate | Pool, Hot Tub & Gardens
///ARCHITECTURAL HOME / BEACH /CBD / CAFE PRECINCT

Yarra Valley Serenity House in Golf Country Club

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

Tanglewood

Ultralux Absolute Beachfront with Extra Studio
Weekly house rentals

Gate Access to the Beach

Bushland Getaway

A Sylvia Home in Deepdene

Elegant Caulfield North Family Home

Parkdale Beach + Village base

Brilliant Bungalow Home at Oakleigh and Chadstone

House of Windsor

Gerty Longroom: Rooftop onsen & fresh produce
Private house rentals

The Black Cockatoo

Osborne Cottage by the Beach

Designer Sun-Drenched Oasis in Heart of Yarraville

The Beach House: Waterfront with Boat Mooring

George on George

Welcome to Chakra, A warm and peaceful home

Holly Hill Cottage

Luxury Mountain Retreat in the Dandenong Ranges
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $140 SGD | $84 SGD | $118 SGD | $220 SGD | $100 SGD | $103 SGD | $131 SGD | $142 SGD | $159 SGD | $118 SGD | $156 SGD | $131 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
- Melbourne Holiday rentals
- Yarra River Holiday rentals
- South-East Melbourne Holiday rentals
- Gippsland Holiday rentals
- South West Holiday rentals
- Southbank Holiday rentals
- Canberra Holiday rentals
- Docklands Holiday rentals
- St Kilda Holiday rentals
- Apollo Bay Holiday rentals
- Launceston Holiday rentals
- Torquay Holiday rentals
- Fitness-friendly rentals Cheltenham
- Family-friendly rentals Cheltenham
- Rentals with a sauna Cheltenham
- Rentals with pools Cheltenham
- Rentals with a hot tub Cheltenham
- Pet-friendly rentals Cheltenham
- Smoking-friendly rentals Cheltenham
- Flat rentals Cheltenham
- Rentals with outdoor seating Cheltenham
- Rentals with a patio Cheltenham
- Rentals with a washing machine and dryer Cheltenham
- House rentals Victoria
- House rentals Australia
- 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
- Smiths Beach
- Sorrento Back Beach
- Puffing Billy Railway
- Torquay Beach
- Geelong Waterfront
- Melbourne City Centre
- Royal Botanic Gardens Victoria
- AAMI Park
- Flemington Racecourse
- Mount Martha Beach North
- West Side Place
- West Richmond Station





