Vacation rentals in Oakville

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Top-rated vacation rentals in Oakville

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Top guest favorite

A cozy fire pit sits in the foreground, surrounded by log stools. The tiny home is visible in the background, its large windows illuminating the dark, serene landscape with a warm glow. Trees frame the scene, enhancing the intimate outdoor atmosphere.

Tiny home in Yellow Rock

4.97 out of 5 average rating, 115 reviews

Tiny Bush Escape Blue Mountains

Adults-Only Tiny Home | Bush Escape | 1.5hrs from Sydney Looking to truly unwind? This peaceful, adults-only retreat is tucked away among the trees in the lower Blue Mountains – the perfect spot to slow down, reconnect with nature, and exhale. Experience the “tiny home” lifestyle in what was once a 40ft shipping container. This beautiful tiny home has been thoughtfully transformed into a luxurious escape for couples, solo travellers, or close friends looking to recharge in privacy and comfort

Top guest favorite

Cottage in Kurrajong Heights

4.98 out of 5 average rating, 323 reviews

MontPierre Rustic & Cosy Mountain Cottage

Experience a window into mountain life in this private hilltop hideaway surrounded by trees. Suited to those wanting an authentic rustic mountain getaway where a mix of relaxation and adventure awaits. Enjoy the simple pleasures of log fires, outdoor vintage hot bath & wood fired pizza oven. Hosts Prue & Mathieu are kind and caring mountain folk who enjoy sharing a slice of their charming property in a fully self contained guest cottage perched on the side of a hill boasting valley views.

Top guest favorite

A group of alpacas can be seen grazing in a natural setting, surrounded by trees and open land. Their distinctive features and unique fur textures stand out, with some blending into the greenery of the landscape.

Guesthouse in Ebenezer

4.99 out of 5 average rating, 113 reviews

Quiet country getaway in stylish 2 bdrm shed

A cosy and warmly appointed former workshed, set in a quiet corner of our property. Complete with kitchen, aircon, bbq and outdoor fire, it’s ideal for a weekend getaway with small, well behaved dogs welcome. Free Wi-Fi and Netflix, along with the beautiful outdoor pool and heated spa, ensure a relaxing time. You’ll enjoy beautiful sunsets, the odd wandering kangaroo, alpaca, horse, frog, chicken and local birds. Nearby wineries, markets, and a vibrant food culture make for a lovely escape.

Superhost

The cabin's entrance features a wooden door framed by large glass panels, allowing for natural light. Two metal chairs are positioned on the covered porch, with wooden flooring leading to a welcome mat. Greenery is visible in the backdrop, enhancing the serene environment.

Cabin in Maraylya

4.76 out of 5 average rating, 156 reviews

The Kickback Cabin

The Kickback Cabin is located on a rural acreage property just an hour from Sydney. It is tucked away in our back paddock, looking out onto the last remains of Cumberland Forrest in the Sydney Basin. It’s a great space to simply kickback, enjoy a glass of wine, a walk in the adjacent Scheyville National Park, Longneck Lagoon, nearby Mitchell Park or Cattai National Park. Situated 5 minutes from Pitt Town and the Hawkesbury River, the Kickback Cabin is close to local pubs and cafes too.

Superhost

A modern wooden door with multiple frosted glass panels invites guests into the granny flat. The soft lighting from the interior illuminates the entryway, highlighting the warm tones of the door and the sleek flooring visible through the open doorway.

Townhouse in Bella Vista

4.81 out of 5 average rating, 506 reviews

Modern & Spacious Granny Flat in Bella Vista

RIGHT IN THE HEART OF BELLA VISTA ! Well-lit & modern 1 bedroom granny flat with spacious kitchen and bedroom. Has separate side entry from main house so guests have full privacy. Kitchen with white goods and cooking utensils. Equipped with air con and Wi-Fi. Has courtyard seating outside. Living room with sofa bed and TV. Comfortable queen bed in bedroom with en-suite bathroom attached. Convenient location close to Norwest business park and walking distance to public transport!

Top guest favorite

An outdoor alfresco area features comfortable seating arrangements complemented by a coffee table. Nearby, a table tennis setup is positioned, surrounded by lush greenery and the inviting lagoon pool. A pink pool float adds a playful touch to the tranquil setting.

Home in Pitt Town

5 out of 5 average rating, 24 reviews

Avondale Luxe Country Retreat in the Hawkesbury

Luxe Country Lodge - bushland retreat in Sydney. "Avondale" is a luxe 5-bedroom Country Lodge nestled on the edge of breathtaking Australian Bushland. Just over 1 hour from Sydney and 10 minutes from Windsor, Avondale offers you the perfect blend of relaxation, comfort and activities for everyone young and old. Forget noisy neighbours and city lights; here, the stars come alive in the night sky and the wildlife is abundant. NOTE: Avondale is not a party destination.

Superhost

A wire basket is positioned on a wooden floor, holding several magazines. The cover of 'Home Beautiful' magazine is visible, featuring a green sofa and a dining area. The overall arrangement provides a cozy, well-organized look.

Home in Windsor

4.91 out of 5 average rating, 34 reviews

No28 - 99 years in the heart of Windsor

No28 is a home away from home, centrally located in the heart of Windsor. Being 99 years old, this property has seen a lot in its years and continues to impress with art deco design and a spacious closed in back yard and veranda. Simple yet beautiful, our aim is to provide a comfortable space that works for couples, families or friends wanting to relax, watch dvds, read, play games or explore the local area. Close to shops and amazing restaurants, galleries, and cafes.

Guest favorite

The exterior of Studio 1888 is framed by lush greenery and features a charming stone chimney. A well-maintained garden displays clusters of purple flowers, while a lamppost adds a decorative element, inviting guests to explore the peaceful surroundings.

Guest suite in Faulconbridge

4.9 out of 5 average rating, 363 reviews

Coomassie Studio: the charm of a historic property

This accommodation is ideal for those who prefer the rustic charm of a historic property over modern comforts. Warm and cosy in winter, the studio was once a purpose-built kitchen of a house built in 1888. Separate entrance. Recycled furniture, large bed, sofa, original fireplace and bathroom with shower cabin. Tiny veranda and a kitchenette, shared patio. NO KITCHEN. To use the fireplace, please BYO timber. For groups of 4 PLEASE CHECK OUR TINY COTTAGE next door.

Guest favorite

A wooden deck is surrounded by lush greenery, with a large tree extending overhead. The misty atmosphere softens the view, creating a serene environment. A single chair is positioned on the deck, inviting moments of reflection amidst nature.

Cabin in Mount Tomah

4.97 out of 5 average rating, 177 reviews

The Hill Station at Mt. Tomah

The Hill Station is in the heart of the Blue Mountains World Heritage Area, immediately adjacent to the Mt. Tomah Botanic Gardens. The renovated cabin is set in an acre of gardens and is an ideal retreat for a couple. The cabin has a Living/Bedroom area with one queen bed, a sunny Kitchen and a new Bathroom. There are cafes nearby, the Botanic Gardens are a short walk, and the main towns of the Blue Mountains are 20 minutes drive away.

Top guest favorite

A gray sofa is adorned with several cushions in various shades of green and a striped pattern. A cozy throw drapes across a corner of the couch. Above the sofa, a large framed photograph of two koalas resting on a tree branch adds a natural touch to the space.

Apartment in Rouse Hill

4.98 out of 5 average rating, 94 reviews

Sylish one bedroom unit overlooking piazza

Modern and stylish one-bedroom apartment @Rouse Hill Town Centre, just steps from the metro which will take you directly to Sydney’s CBD in about 40min. Featuring an open-concept layout, sleek finishes, and natural light throughout, this urban retreat offers both comfort and convenience. Perfectly located with cafés, shops, library and cinemas at your doorstep. Also enjoy the use of a pool, gym and tennis courts a short stroll away.

Top guest favorite

An exposed brick wall is featured, showcasing a mixture of earthy tones. A framed artwork is centered above, while two wall sconces are positioned symmetrically on either side, providing soft illumination. Wooden beams are visible above, adding a rustic touch to the room.

Home in Windsor

4.95 out of 5 average rating, 19 reviews

1840s Heritage house in Windsor

Heritage listed 1840s cottage in Windsor. Close to cafes, parks and the Hawkesbury river whilst still peaceful and private. Stay cosy with full zone controlled ducted heating/cooling. Spacious king room and a separate bedroom with twin single beds. The house retains charming original features including a working open fire place. Includes a modern, well equipped kitchen and dining space. Relax in the sunny private courtyard.

Top guest favorite

A wooden sauna is displayed with warm-toned walls and benches made of smooth planks. Soft lighting is provided by a wall-mounted fixture, enhancing the serene atmosphere. The tile floor features a small drain, while the overall layout emphasizes a cozy, relaxing space.

Guesthouse in Windsor

4.92 out of 5 average rating, 498 reviews

1830's converted barn with sauna

This barn dates back to 1830's but it has been fully renovated to a studio apartment with all modern comforts. It is one open space with living area and two sleeping lofts, one with queen bed, the other with 2 single beds. A bit like a giant cubby house! The shops are just 5 minute stroll away, and so is the river and train station. You share a garden with a spa and BBQ with the main house where we live.