Holiday rentals in Medway

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Top-rated holiday rentals in Medway

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A charming Victorian lodge is positioned along a quiet single track road, featuring a welcoming entrance with a white gate and green doors. Surrounding fields and trees are visible in the background under a clear blue sky.
Cottage in Wainscott
5.0 out of 5 average rating, 64 reviews

Victorian gardener's lodge set in Kent countryside

This Victorian gardener's lodge house has recently been refurbished to create an idyllic country escape. Situated just out of town, this pretty country cottage is set within one corner of the main house's walled kitchen garden. Cosy up with a book in front of the log burner, or enjoy a morning coffee in the small cottage garden at the front, with views across arable fields & woodland. Relax with a glass or two on the stone paved terrace at the back of the cottage, the best place for a sundowner.

Guest favourite
A modern dining area features a round table set with plates and flowers, surrounded by four black chairs. A cozy sofa is positioned nearby, with a soft color palette complementing the overall design. Light enters through an opening to the kitchen area.
Home in Rainham
4.96 out of 5 average rating, 157 reviews

Modern 2 Bed House in Rainham, Kent

Welcome to this modern home from home in Rainham, Kent. Perfect for any stay - leisure, work, visiting family/friends & local attractions. Conveniently situated close to local amenities, 5-minute walk to train station and town centre, restaurants, pubs, bars, shops & much more. Including 2 spacious bedrooms with double & king size bed, new luxury bathroom & open lounge with all Virgin TV channels, fast WiFi, fully equipped modern kitchen, large garden & a private parking space for your stay.

Top guest favourite
The exterior of the annex is showcased, featuring vertical wooden slats and a glass-paneled door. A small window is visible, allowing natural light into the space. The entrance is set on a paved path, surrounded by greenery and a water storage tank nearby.
Guest house in Sittingbourne
4.93 out of 5 average rating, 303 reviews

Self-contained annex, with off-road parking.

Self-contained annex in Sittingbourne, perfect if you are visiting the area for work or leisure. Everything you need for a comfortable stay in your own completely private place, with driveway parking and fast WiFi. The accommodation comprises a bedroom /lounge /working room, kitchen and bathroom. The annex, especially the bedroom, is very quiet and peaceful. Located conveniently for the motorway and also easy access to the town centre, train station, shops, takeaways, restaurants and pubs.

Top guest favourite
Home in Rochester
4.92 out of 5 average rating, 212 reviews

2-bedroom house in historic Rochester with Parking

Dove’s Place is a 2 bedroom terraced house with addition of a conservatory space and free allocated parking space. The property is adjacent to River Medway located in Rochester and close to green spaces and guests can also enjoy river walk. It is a walking distance to Rochester Castle, Cathedral, Train Station, High Street Shops, Restaurants, Museums, Coffee Shops and Bars. Great place for Family, Professionals and Tourist. We guarantee a memorable stay with our slogan, HERE FOR YOU!!!

Guest favourite
Home in Lower Upnor
4.98 out of 5 average rating, 44 reviews

Charming Riverside Home in Historic Kent Village

Stylish 3-storey 4-bedroom holiday home in the historic riverside village of Lower Upnor, Kent. Features include a spacious kitchen, cosy lounge with Smart TV, Wi-Fi, 1 main bathroom, en-suite to master, and downstairs WC. Enjoy the terraced garden with outdoor seating. Walk to Upnor Castle, river paths and traditional pubs. Easy access to Rochester, Strood (London trains), A2/M2 and family attractions. Free parking for 2 cars. Ideal for families, groups, professionals or short breaks.

Top guest favourite
A bright living area is present, featuring two dark leather sofas positioned on a plush area rug. A small wooden table holds a vase of flowers. Natural light enters through a skylight, complementing a mounted television and decorative elements on the mantel.
Flat in Rochester
4.99 out of 5 average rating, 72 reviews

Castle Garden View - Central Rochester High Street

Castle Garden View is a 2 bedroom flat situated in a prime location within the bustling heart of Rochester, close to both the Castle and Cathedral. In addition to the many historical landmarks of the local area, visitors can enjoy the vibrant bars and restaurants nearby, providing plenty of dining and entertainment options right on the doorstep. The flat is within easy walking distance of Rochester and Strood railway stations and so ideal for visitors arriving by public transport.

Superhost
A modern living space features a cozy gray sofa draped with a patterned throw. A media console supports a large television, displaying a vibrant image. A geometric rug adds a pop of color, while a tall potted plant introduces natural elements to the room.
Home in Medway
4.95 out of 5 average rating, 21 reviews

Gillingham cosy 3 bedroom with WiFi &free parking

Welcome to our enchanting 3-bedroom retreat! this stylish haven offers a perfect blend of comfort and luxury. Immerse yourself in the charm of modern amenities, including a fully equipped kitchen, cozy living spaces, and a private garden. Whether you're unwinding indoors or enjoying the picturesque surroundings, this tranquil escape promises a rejuvenating stay. Ideal for families or groups seeking an unforgettable getaway. Book now and experience the magic of our delightful home!

Guest favourite
The living room features a large smart TV displaying the Netflix logo. A dark sectional sofa with decorative pillows and two comfortable armchairs surround a circular wooden coffee table. Natural light floods in through patio doors, highlighting the clean, modern design.
Home in Medway
5.0 out of 5 average rating, 15 reviews

Extraordinary Tranquil Rochester|Free Parking X 2

Discover the perfect blend of comfort, style, and convenience at our thoughtfully designed space. • Bright, clean, and beautifully furnished • Super comfy beds 2000 pocket mattress • Quiet neighborhood yet close to all the local amenities • Private garden and space to unwind Whether you’re visiting for a weekend getaway, a business trip, or a longer stay, we’ve made sure you’ll have everything you need for a comfortable experience. Come stay with us, we’d love to host you!

Top guest favourite
Guest house in Medway
4.98 out of 5 average rating, 42 reviews

The Back Garden Annex – Welcoming and Witty

Welcome to Your Cozy Garden Annex in Twydall! Are you visiting family nearby or setting out to explore Kent, the Garden of England? Our charming self-contained garden annex offers a warm, homely space where you can relax, recharge, and feel right at home. Perfectly located in Twydall, just a five-minute drive from Rainham, Kent train station, you’ll have direct links to central London and Kent’s iconic seaside towns — from Whitstable’s oysters to Margate’s sandy shores.

Guest favourite
Home in Medway
4.93 out of 5 average rating, 114 reviews

Grade II 3-bed cottage• Free parking • Sonos & 5.1

Enjoy a stylish experience at this centrally-located cottage in the heart of Rochester. The Grade 2 listed cottage was built in the 1750s but has all the comforts of high end residential living. With SONOS speakers throughout, Sky TV and 5.1 Surround sound in the lounge you have the perfect retreat if you want to relax. Town is a two minute walk if you want a drink, or make your own at the cocktail bar. The lit terrace makes the perfect place to read , eat or party.

Top guest favourite
A charming two-story building features a classic white-clapboard façade with a large window on the upper level. The entryway is framed by a beige curtain, while greenery is visible in front of the structure. Adjacent buildings showcase brick and painted exteriors.
Cottage in Rochester
4.95 out of 5 average rating, 326 reviews

The Old Tuck Shop (entire cottage - 1 double bed)

Ideally located for exploration of the historic Medway Towns and surrounding areas of Kent,The Old Tuck Shop is the perfect place for a relaxing getaway. The accommodation can sleep up to 3 guests, but this listing is only for two guests sharing the double room. If the second single bedroom is required please contact your host before booking or see the other listing. There is a full bathroom upstairs and an additional loo and cloakroom downstairs.

Top guest favourite
A light-filled hallway with warm wood flooring is lined with elegant wall paneling. A potted plant sits in a gold planter, adding a touch of greenery. Soft pink walls create a welcoming atmosphere, with an inviting peek of a bedroom visible through the archway.
Flat in Rochester
4.95 out of 5 average rating, 41 reviews

The Corner by the Castle

The Corner by the Castle is our characterful first floor Victorian apartment in the heart of Rochester High Street. Sleeping 4 with two comfy double beds, a great kitchen (where you can catch a glimpse of the castle gardens from the window) it’s perfect for relaxing or exploring. Surrounded by shops, restaurants, and historic sites like Rochester Cathedral and Castle, it’s the ideal base to enjoy everything this charming City has to offer.

Popular amenities for Medway holiday rentals