Plan your trip

Search Holiday Rentals in Medway

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key

    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

  • Check prices for these dates

    Check prices for these dates, 13 – 14 December 2026

    View in a map

    Our top choices for Medway holiday rentals

    1. The Sebel Bowral Heritage Park

    Exterior

    2. A unique Southern Highlands experience

    A wooden cabin with a metal roof, surrounded by lush greenery and flowering plants.

    3. Belle in Bowral - walk to town

    A modern living room with a grey sofa, a dining area, and a kitchen with stainless steel appliances.

    4. Bluebell – centrally located apartment

    A balcony with green cushioned seating, a grill, and a view of neighboring houses.

    5. Banyula Annex - superb contemporary styling and modern amenities

    A spacious living room with a large sofa, a dining table with chairs, and a fireplace.

    6. Romantic Stone Cottage Overlooking Pond. 5mins to Town

    A spacious living area with a high ceiling, wooden beams, a sofa, armchairs, a coffee table, and a kitchen in the background.

    7. 8 on Clarence - perfectly located in the centre of town

    A dining table set with white plates, glasses, and a vase with green leaves.

    8. French Boutique The Loft Apartment @Chapmans+Pets+B'fast

    A garden with a stone pathway, various shrubs, and trees.

    9. Charming 1-Bed Cottage in Historic Berrima

    A covered porch with wicker furniture, a table, and a hanging planter.

    10. Burradoo Loft with king size bed. Close to Southern Highlands wineries.

    A two-story building with a green roof, surrounded by a well-maintained lawn and flowering plants.

    11. Garden loft studio 7 minutes walk to Exeter village centre

    A spacious bedroom with a large bed, a desk, and a view of the outdoors.

    12. Mirambeena - Welcoming retreat in Berrima with gardens, firepit & easy family comfort

    A modern interior with a sliding door, a console table, and a dining area in the background.

    13. Windermere – stunning and garden setting

    A two-story building with a balcony, surrounded by well-manicured hedges and tall trees.

    14. Saint Eloi - Le studio

    An outdoor dining area with a wooden table and chairs, surrounded by greenery.

    15. Little Possum Retreat | Spa, Fire, Pet Friendly & Walkable

    A room with a fireplace, a window, and a view of trees outside.

    16. The Willows Circa 1917 | Historic Bowral Cottage

    A bedroom with a bed, bedside tables, a wardrobe, and a sliding glass door leading to an outdoor area.

    17. Possum Pines – family friendly Highlands escape with games room, firepit and luxe ensuite retreat

    A modern living room with a sofa set, a coffee table, and a red patterned rug.

    18. The Bunkhouse - quality, contemporary home

    A modern kitchen with white cabinetry, a central island, and a dining area with a wooden table and white chairs.

    19. Willowmere - family fun awaits with spacious gardens, a games room, fire pit and room to relax

    Windermere | Wi-Fi | Sunroom with Smart TV and Arcade style game | Soccer field | Firepit

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

    View all properties

    Find holiday rentals that suit your style

    Apartments

    Apa · rtments

    Cabins

    Condos

    Cottages

    Villas

    Top Medway Hotel Reviews

    Berrima Bakehouse Motel

    A garden with a wall covered in climbing roses, a wooden fence, and various other plants.

    Links House

    A cozy room with a sofa, a round table with two glasses of wine, and a lamp.

    Osborn House

    A modern indoor pool with a glass ceiling, lounge chairs, and potted plants.

    Berida Hotel

    A room with a brick wall, a large arched window, a chandelier, a plant, and a desk with a computer.

    The Gibraltar Bowral

    A modern spa area with wooden flooring, large windows, and wicker loungers.

    The Bowral Hotel

    A modern bedroom with a large bed, a nightstand, a dresser, and a bathroom visible through an open door.

    The Sebel Bowral Heritage Park

    Exterior

    The Imperial Motel

    A bar with a brick wall, wooden ceiling beams, and shelves stocked with bottles.

    The Laurels B&B Kangaroo Valley

    A bedroom with a wooden bed, a window, and a view of greenery.

    Peppers Manor House

    A dining table set with a tiered dessert stand, glasses, and cutlery.

    The Dormie House - On The Golf Course

    A neatly made bed with a white headboard and two green pillows, a framed artwork above the bed, and a bedside table with a lamp.

    Moss Vale Holiday Park

    A modern living space with a dining area, a sofa, and a flat-screen TV mounted on the wall.

    Mittagong Motel

    A covered outdoor area with a wooden table, a blue mat, and potted plants.

    Scribbly Farm Premium Dome Bush retreat Southern highlands

    A tented accommodation with a bed, seating area, and a view of the outdoors.

    Find out more about Medway

    Everything you need to know about Medway holiday rentals

    Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Medway holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Medway holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Medway holiday rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Medway. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

    Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Medway holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Medway holiday rentals we have selected for you start as low as £108 per night. Entering your travel dates in the search wizard you might find even better deals!

    How to find incredible deals on Medway rentals

    At Expedia, we put the best Medway holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Medway rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Medway holiday.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Medway. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Can I find a holiday rental in Medway?

    Yes, there are holiday rentals close to the most popular sights in Medway, or you can select a more secluded option if you're looking for a relaxing stay.

    What are some of the best holiday rentals that Medway has to offer?

    Hillside Farm – Rural getaway on 100 acres of sweeping farmland: This holiday home rental outside of Medway offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of table football in this rental home to help you unwind.

    How many holiday rentals will I find in Medway?

    With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Medway stay.

    What can I see and do in Medway?

    While exploring the area, visit family-friendly sights like Bendooley Estate Book Barn, or get outside and enjoy nature at Corbett Gardens. In the wider area, you’ll find Berrima Gaol and Harper's Mansion.

    What are holiday rentals like in Medway?

    Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Medway. Holiday rentals offer extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for families.