Vacation rentals in Cooling

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Top-rated vacation rentals in Cooling

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Top guest favorite

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 out of 5 average rating, 22 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.

Superhost

A spacious living area is highlighted by a green sofa and a cozy armchair arranged around a decorative rug. A fireplace with a decorative mantel serves as a focal point, while light filters in through nearby windows. Original features add character to the space.

Home in Cliffe

4.77 out of 5 average rating, 26 reviews

Thompson Cottage

A humbly restored home from home. With everything you need to enjoy a stay near the marshes. Located towards the end of the village of Cliffe this 2 bedroomed terraced cottage has all you need for a comfortable stay. Built in the 1860's with a modern kitchen and bathroom extension Thompson Cottage has the character of an old building, with the comfort of modern amenities. Lounge, kitchen and bathroom are located on the ground floor, 2 bedroom upstairs with a cellar and garden for extra space.

Guest favorite

An open-plan lounge is featured with a plush sofa and a smart TV mounted on the wall. A decorative fireplace adds character, while large windows allow ample natural light. A carpeted area is enhanced by a coffee table and a cozy blanket.

Apartment in Medway

4.93 out of 5 average rating, 14 reviews

Cosy Gillingham Stay • WiFi • Train • Parking

✨ Comfortable Getaway in Gillingham ✨ This modern 1-bedroom retreat is perfect for solo travellers, couples, or professionals. ✔ Inviting Living Space – Open lounge with plush sofa, smart TV & natural light. ✔ Fully Equipped Kitchen – Everything you need to cook with ease. ✔ Serene Bedroom – Double & single beds with great storage. ✔ Prime Location – Steps from shops & Gillingham Station with direct trains to Central London or Kent's beautiful seaside towns. 📅 Book now for your perfect stay!

Top guest favorite

A well-maintained garden is framed by lush greenery, showcasing vibrant flower beds and neatly trimmed hedges. Beyond the garden, expansive views of rolling hills and the Darent Valley can be seen under a partly cloudy sky.

Condo in Otford

4.99 out of 5 average rating, 132 reviews

Stunning Views over Garden & Valley

Wake up & lift the automatic blinds directly from your SUPER KING SIZE BED & be captivated by the VIEW of the beautiful Darent Valley unfolding before you through the picture windows. SNUGGLE in a cosy armchair with a book, listen to your favourite music or EXPLORE many footpaths along the valley. Stroll through the fields to Otford & Shoreham villages, visit HISTORIC HOUSES & vineyards or simply stay at home & enjoy a spacious studio apartment whilst staring at the sunset with a glass of wine

Top guest favorite

A scenic river view displays a ferry transporting passengers across the water. In the background, a large cruise ship is visible. Lush greenery frames the scene, while the calm water reflects the clear blue sky.

Townhouse in Gravesend

4.98 out of 5 average rating, 239 reviews

*NEW* Luxury Thames View Riverfront + Home Cinema

The PERFECT place for your getaway, this luxury property is a great base to explore Kent whilst only 23 mins to London on the train. Grade II listed fully renovated, modern Thames River view townhouse with a Home Cinema! With fantastic riverside views, this 2 Bedroom property sleeps 4 & has off road parking. Recently renovated to a high standard with new home cinema, kitchen, bathroom, bedrooms & furniture and decorated for xmas . Come and spend time in our unique riverside property in Kent.

Guest favorite

A two-story white building features large glass panels on the front, allowing natural light to illuminate the interior. The entrance is accentuated by decorative stone columns on either side. A paved area with gravel is visible in the foreground.

Guest suite in North Benfleet

4.96 out of 5 average rating, 379 reviews

Adorable 4 bedroom annex with hot tub

Welcome to 'The Annex' a super hidden gem, tucked away in a rural location but only 11 miles to Southend seaside with 'Adventure Island', 8 miles to Leigh-on-sea and only 33 miles from London. Nestled between the A13 and A127. 'The Annex' is the perfect setting for special occasions, birthdays, treat yourself time, hens, contractors, business bookings. Take time to relax in the bubbly hot tub. It's important to look at 'other details to note' for rules on events, celebrations and gatherings.

Top guest favorite

A spacious sleeping area is featured with a black metal bed frame, soft-textured pillows, and a bright yellow throw draped over the bed. The wall behind is adorned with a mural of trees, complemented by a wooden chest of drawers and dark curtains.

Home in Cliffe

4.95 out of 5 average rating, 152 reviews

Cosy 1 bed countryside cottage, tranquil location

Very spacious 1 bed en-suite cottage with off road parking and a small courtyard area. Formerly an Annex to the main house it is ideally situated for walking/hiking with easy access to the RSPB marshes of Cliffe. Beautiful views of the Kent countryside leading to Cooling Castle Barn, St Helens Church, Cliffe and St James church which inspired Charles Dickens to write Great Expectations where the hero Pip met Magwitch the convict. Easy car access to Historic Rochester Castle and Cathedral.

Guest favorite

The living area features exposed wooden beams, complimented by a cozy two-seater sofa and a reading chair. A round coffee table sits at the center, with natural light illuminating the space through multiple windows. A flat-screen TV is mounted on the brick wall.

Cottage in Allhallows

4.92 out of 5 average rating, 13 reviews

Charming cottage with hot tub & private garden

Nestled in the heart of the serene village of St. Mary Hoo, our cottage offers a unique escape into the tranquility of the Kent countryside. This retreat offers a sanctuary where guests can truly relax and rejuvenate, with the help of a private garden and hot tub. Whether you’re a family on holiday, a couple in search of a peaceful countryside retreat, or a professional needing a quiet and comfortable place to unwind after a long day’s work – our cottage provides the ideal sanctuary.

Guest favorite

An inviting entrance features a classic door framed by a brick wall. A decorative hanging basket filled with colorful flowers adds a touch of charm, while warm light from inside highlights the cozy atmosphere of the cottage.

Cottage in Cliffe

4.95 out of 5 average rating, 103 reviews

A rural retreat, near Rochester

An ideal alternative to a hotel, Chantry Cottage offers the flexibility of self catering, where care and attention has gone into providing the perfect stay. Inside the cosy accomodation ancient timbers are paired with twists of antique luxuries and modern influences in which to relax and enjoy. Externally, the private pretty cottage garden is complete with patio furniture, pizza oven, bbq perfect for eating alfresco. For cyclists there’s a shed large enough to store the bikes.

Top guest favorite

A dining area features a round table with wicker placemats, surrounded by black chairs. A potted plant adds a touch of greenery. Large windows offer views of the marina, showcasing boats and water reflections under a soft sky.

Apartment in Saint Mary's Island

5 out of 5 average rating, 62 reviews

Stunning 2 Bed Chatham Docks Apartment

This stunning 2 bed apartment is the perfect place to relax and unwind situated on the marina. Come and explore the sights and local attractions of historical town of Chatham. Surrounded by restaurants, shops, bars and a multiplex cinema. Also has excellent connections to London with 2 stations being within a 10 minute drive and only taking 40 minutes to get into London via high speed making it the perfect stay for tourists and business stays.

Guest favorite

A charming barn conversion is depicted amidst a grassy landscape, with a gravel driveway leading to its entrance. The structure features black wooden siding and a metal roof, surrounded by rows of pear orchards and open farmland under a partly cloudy sky.

Farm stay in Medway

4.93 out of 5 average rating, 167 reviews

Unique barn conversion with beautiful marsh views

This recently converted barn is situated on the edge of the North Kent Marshes, with stunning views of the birds and wildlife on the marshes and surrounded by pear orchards to the rear. You’ll enjoy complete privacy, with no surrounding properties and a real sense of peace and tranquillity. The property is located in the middle of a working farm, with our sheep grazing the marshes and a variety of fruit grown in the orchards.

Guest favorite

A newly converted barn features a blend of rustic brick and dark timber siding. The entrance is framed by wooden doors, and a spacious patio area is highlighted by a wooden table and chairs. Lush greenery surrounds the structure, offering a serene outdoor setting.

Guesthouse in Cliffe

4.9 out of 5 average rating, 121 reviews

Bull Lodge

Relax with the whole family at this peaceful place to stay, come for a quiet getaway or be inspired to explore the local walks and nature reserve. Bull Lodge is newly converted, but comes with lots of history. On the site of the village's Manor Farmhouse, this was where the bull was housed for the once busy dairy farm. Now it is tucked away in a quiet corner amongst newly converted barns and behind the original farmhouse.