
Holiday houses in Medway
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Top-rated holiday rentals in Medway
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Luxstowe Cottage
Luxstowe House is a historic cottage surrounded by wild, sprawling gardens on acres of land hidden just 5 mins drive from Bowral. Brimming with beautiful artworks and an abundance of books - it's a home you will never want to leave! The sweet country cottage is set at the bottom of a tree-lined drive and below an old barn once used as a sculpture studio and now as a tree nursery. Only 1.5 hours from Sydney, it will transport you to another world so you can relax & recharge on your next getaway.
4.84 out of 5 average rating, 212 reviews
Farm stay at Melaleuca cottage
Escape to our cozy cottage on a 100-acre farm, where mountain views greet you at every turn. Cool off in the plunge pool or soak in the wood-fired hot tub under open skies. As the sun sets, gather around the fire pit and enjoy the tranquility of the starlit night. Surrounded by Nattai National Park, you’ll be immersed in nature – with birdsong, fresh air, and stunning scenery. Whether you're after adventure or a peaceful retreat, this setting offers the perfect blend of comfort and relaxation.
4.96 out of 5 average rating, 111 reviews
2-Bedroom apartment located in the heart of Bowral
Located in the heart of Bowral, this charming 2-bedroom home is perfectly positioned within walking distance to the town centre, local cafes and shopping as well as renowned Bradman Oval. Offering a timeless contemporary feel, the space features a relaxing living area with accompanying fireplace, modern kitchen, sun soaked deck, 2 bathrooms and spacious dining area. The home is surrounded by a beautiful, mature and private garden and is a short distance walk to the town's Cherry Tree walk.
4.97 out of 5 average rating, 203 reviews
Luxury Country Escape at Colyersdale Cottage
Set on a 350 acre cattle property 10 minutes from Moss Vale you will find this purpose built, luxurious Hampton’s style cottage. With a 2 car connected garage and indoor/outdoor sandstone fireplace, it comprises 2 large king bedrooms each with a walk-in robe and ensuite. There is ducted air conditioning, fully appointed kitchen, open plan living dining, concealed laundry, outdoor dining terrace, swinging seat and BBQ. Perfect for 2 couples or a family of 4 or 5. Message me for longer stays.
5.0 out of 5 average rating, 241 reviews
Kangaroo Cabin - Luxurious Simplicity in Berrima
A peaceful retreat that’s only a 5 minute walk to the centre of Berrima, 3 minute drive to Bendooley Estate and 6 min’s to Centennial Vineyards. It’s a space that’s been designed to help you relax, and get away from it all, although you’ll still find every modern convenience you could possibly need. It also feels surprisingly large for a tiny home, with light streaming in the windows from your own private garden and the bushland beyond. And, yes, there are Kangaroos out there, all the time.
4.97 out of 5 average rating, 186 reviews
Lyre's Cottage | Private Berrima Escape
Beautifully appointed, Lyre’s Cottage is the perfect retreat in the idyllic Southern Highlands. The spacious studio features a generous living area, a secluded queen sleeping area, well-equipped kitchenette, slow-combustion fireplace, and private garden with an outdoor fire pit. Just a short stroll from the historic pubs, restaurants and cafés of Berrima village, Lyre’s Cottage offers the best of both worlds—village convenience in a peaceful bush setting, surrounded by native birdlife.
5.0 out of 5 average rating, 128 reviews
"The Burrow", Mittagong, Southern Highlands, NSW
“The Burrow” is a self-contained cottage on a 100 acre wildlife sanctuary just 5km from the centre of Mittagong. Once you arrive, it's just you and a few hundred kangaroos and a wombat or two. We invite you to take in nature at your own pace in this peaceful & private setting. “The Burrow” is a hand-built, mud-brick cottage set on the Southern Highlands of NSW. It's quirky yet very comfortable. With nature & wildlife all around we want you to feel like you're 1000 miles from anywhere.
4.95 out of 5 average rating, 392 reviews
Fantoosh
Welcome to your blissful getaway! This beautifully designed picture-perfect cottage is nestled in the heart of Sutton Forest, the ideal fit for anyone looking to relax and unwind. Enjoy the heated floors and an Internal fire at the press of a button. Firepit outside awaits, sizzle a steak or toast marshmallows under the stars. Snuggle up on the couch, stream a movie you never got to see or work on the super fast internet. Take a walk along the country lanes and enjoy the fresh air.
4.99 out of 5 average rating, 169 reviews
The Stables at Long Paddock
The Stables is a self contained guesthouse situated on our family property in beautiful Burradoo. Suited to either a family of up to four or two couples, the guesthouse is fully equipped for a weekend away in the countryside. Located midway between Bowral and Moss Vale, the Stables is set on 10 picturesque acres and surrounded by unspoilt farmland, with views to Oxley Hill and surrounds - yet Bowral’s boutiques, homewares stores, restaurants and cafes are just 5 minutes away.
4.92 out of 5 average rating, 435 reviews
Ardleigh Cottage in Berrima Village
Situated in the heart of historic Berrima, Ardleigh Cottage offers the discerning traveller all of the comforts of home in a tranquil and relaxing garden setting. Quiet yet very close to the many attractions of Berrima, this private abode is the perfect place for your Highlands stay. A historic pub, a cellar door, galleries, speciality shops, cafes, restaurants, historical places of interest and beautiful bush walks are all within walking distance from the cottage.
4.98 out of 5 average rating, 491 reviews
'Rosevilla' in Berrima.
Built in 1883, this gorgeous historic cottage is right in the heart of Berrima village, within easy walking distance of exceptional restaurants and cafes, quaint local shops, historic buildings, the beautiful river and Australia's oldest continually licensed inn. Bendooley Estate is only a 5-minute drive away, making the cottage an ideal choice for wedding guests. Numerous wineries and Berkelouw Book Barn are all close by.
4.9 out of 5 average rating, 272 reviews
Highlands Country Cottage
Highlands Country Cottage offers guests a peaceful escape in the beautiful Southern Highlands. Located on a picturesque 5 acre property between Bowral and Berrima, our one bedroom cottage can be accessed via a country lane with stunning views. The cottage can act as a convenient base for you to enjoy all the Highlands has to offer, as well as somewhere where you can relax and recharge throughout your stay.
4.98 out of 5 average rating, 103 reviewsPopular amenities for Medway holiday rentals
Stay near Medway's top sights
Other great holiday rentals in Medway

Orchard Cottage & Gardens
4.98 out of 5 average rating, 376 reviews
Cosy Bowral Hideaway
4.96 out of 5 average rating, 481 reviews
Cottage on Kings
4.91 out of 5 average rating, 128 reviews
Buskers End
5.0 out of 5 average rating, 485 reviews
Japanese Studio Fitzroy Falls
4.99 out of 5 average rating, 636 reviews
The Villa @ The Vale Penrose
4.99 out of 5 average rating, 341 reviews
Wembley Cottage, Southern Highlands
5.0 out of 5 average rating, 17 reviews
Luxury Glamping in Berrima (Wallaby Grove)
4.95 out of 5 average rating, 19 reviewsDestinations to explore
- Sydney Holiday rentals
- Wollongong Holiday rentals
- Cessnock Holiday rentals
- Port Macquarie Holiday rentals
- Canberra Holiday rentals
- Blue Mountains Holiday rentals
- Kiama Holiday rentals
- Hunter valley Holiday rentals
- Nelson Bay Holiday rentals
- Jervis Bay Holiday rentals
- Bright Holiday rentals
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- Wollongong Beach
- Coledale Beach
- Garie Beach
- Wombarra Beach
- Jamberoo Action Park
- Sea Cliff Bridge
- Killalea Beach
- Bombo Beach
- Kangaroo Valley Golf And Country Retreat
- Merribee
- Jones Beach
- Ocean Farm
- Fo Guang Shan Nan Tien Temple
- Minnamurra Rainforest Centre
- Shoalhaven Zoo
- Stanwell Park Beach
- The International Cricket Hall of Fame
- Figure Eight Pools
- Fitzroy Falls
- Mount Annan Botanic Garden
- Kiama Surf Beach
- Carrington Falls Picnic Area
- Hars Aviation Museum
- Kiama Lighthouse





