Holiday houses in Cooling

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Top-rated holiday rentals in Cooling

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Top 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 Mark
4.97 out of 5 average rating, 135 reviews

Modern 2 Bed House in Rainham, Kent

Welcome to this modern home from home in Rainham. 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 & more. Including 2 spacious bedrooms with double & king size bed, new luxury bathroom & open lounge with all Virgin TV channels including Sky Sports & Netflix, fully equipped modern kitchen, large garden & a parking space for your stay.

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 out of 5 average rating, 31 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.

Top Guest favourite
A spacious home cinema setup is featured, showcasing a large screen displaying a snowy mountain landscape. Soft carpeting covers the floor, with an inviting seating area in front. A staircase is visible in the background, leading to an upper level.
Townhouse in Gravesend
4.98 out of 5 average rating, 246 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.

Top Guest favourite
A wooden cabin with a green roof is surrounded by grass and trees. Two arched windows and a double door provide a welcoming entrance. A small outdoor seating area features two chairs and a table, complemented by decorative stones along the pathway.
Hut in Thurrock
4.97 out of 5 average rating, 145 reviews

The duckhouse

Peaceful retreat on the edge of the nature reserve with a variety of hens ducks outside your window to wake up in the morning 😊 a self contained cabin with all the mod cons in a shabby chic style. Sleeps up to 4 with bathroom and kitchenette. Close to wedding venues, lovely walks, cycling routes, golf courses, easy routes Into London and lakeside shopping centre. Dog friendly with a secure garden, free parking. Animal lovers haven. Green 🦜 and geese flying above with peacocks in the grounds.

Top Guest favourite
A quaint entrance is framed by a variety of colorful flowers, including pink and purple blooms, cascading from hanging baskets and garden beds. The rustic wooden door is set against a whitewashed wall, complementing the charming brick pathway leading up to it.
Place to stay in Addington
4.98 out of 5 average rating, 226 reviews

Petite Gite in an idyllic cottage garden.

Come and make yourself at home in this unique hand crafted miniature gite. Tucked away in the garden of a Tudor cottage, situated on the Addington village green just yards from the Angel Inn. Cottage style Kitchenette with miniature Belfast sink and cupboards. Small double raised bed with storage and dining table underneath. Fully centrally heated for those cosy winter/autumnal days. Rose Cottage, as we call it, has been painstakingly restored to create a delightful, light and cosy space.

Guest favourite
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
4.94 out of 5 average rating, 163 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 favourite
A charming black outbuilding is framed by lush greenery and trees. A gravel path leads to the entrance, surrounded by well-maintained landscaping. The rustic exterior blends naturally with the tranquil rural setting.
Cabin in Rochester
4.95 out of 5 average rating, 436 reviews

Countryside Cabin with Private Patio

The Snuggery is a converted outbuilding that has been set up for a cosy stay with a wood burning stove and lots of snuggly wraps to cuddle up in. The open plan interior, high vaulted ceilings and natural oak flooring create an interior which is fun, light and airy. Walking enthusiasts will enjoy walks from the back door straight on to the North Downs Way and there is a bench by the front door fitted with a heated element, perfect for warming up your walking boots. Photos by Chloe-Rae 

Guest favourite
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
4.94 out of 5 average rating, 18 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 favourite
The historic building showcases a striking façade featuring elegant arches and ornate detailing. Bright sunlight highlights the red exterior, drawing attention to the large windows and decorative elements. The structure reflects its original purpose as a theatre, adding character to the surrounding street.
Apartment in Medway
4.88 out of 5 average rating, 42 reviews

Stunning & Unique 1 bed flat!

Stunning & unique furnished 1 bed flat with mezzanine in Chatham High Road. Building originally a Theatre hosting Charlie Chaplin and Laurel & Hardy. * Very comfortable & high quality property. * \\Please let us know as soon as possible if you require parking in the gated car park (£7.50 per night)// * Large spacious flat / 1200 SqFt * Finished to high standard * No Smoking * No Pets * Walking distance to Chatham Station * Downstairs Utility & WC * WiFi * Dressing & Work area

Top Guest favourite
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, 73 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 favourite
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, 174 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.

Superhost
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
4.88 out of 5 average rating, 130 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 converted barn, which 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.

Popular amenities for Cooling holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Medway
  5. Cooling