Holiday houses in Cooling

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Top-rated holiday rentals in Cooling

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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 out of 5 average rating, 56 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 relaxed bedroom setting features a spacious bed with neutral-toned linens and decorative pillows. A small bedside table holds a minimalist lamp. Natural light filters through the window, enhancing the subtle color palette of the room.
Cabin in High Halstow
4.95 out of 5 average rating, 197 reviews

Cosy cabin in the countryside.

Kent's countryside cosy cabin, set in a garden with a gated front for security. The cabin offers accomodation with 2bedrs & 2bathrs with a fully E.K. Outdoor patio with table and chairs, BBQ area. Within easy reach of London the cabin is 18min. from Ebbsfleet st with a direct link to London St Pancras in 17min. Within 35min you in London, ideal for professionals. Walking distance to local pubs, 5min drive to shops and 12 min drive to Cooling Castle and Knowle Country House - wedding venues.

Superhost
A person stands on a deck overlooking a tranquil lake, accompanied by a dog. The sun shines brightly in the clear sky, casting shadows on the wooden floor. Lush greenery is visible in the background, enhancing the serene atmosphere.
Cabin in Cliffe
4.79 out of 5 average rating, 57 reviews

Swan Lakeside Cabin with Sauna in Nature Reserve

Take it easy at this unique and tranquil getaway at Eternal Lake Nature Reserve, home of Pureplanet Vegetarian & Vegan Biodynamic and Organic Cafe & Shop, set in a tranquil 70 acre nature reserve with 1.5 miles circular walk. Earn a well earnt rest in this beautiful part of the Thames peninsular set 10 minutes drive from the City of Rochester and historic Medway. The Cabin has a superking size bed, ideal for two and has a breathtaking view with plenty of fishy friends to keep you company!

Top Guest favourite
Cabin in Rochester
4.96 out of 5 average rating, 501 reviews

Cosy Rural Retreat with Log Burner

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 

Top Guest favourite
An elegantly designed bedroom features a spacious super king bed adorned with soft linens and stacked towels. A freestanding bath is positioned nearby, complemented by wooden wall accents. A cozy robe hangs in the background, while soft lighting contributes to a serene atmosphere.
Farm stay in Essex
4.98 out of 5 average rating, 381 reviews

Exclusive retreat on a private lake

Enjoy a truly unique stay in this exclusive lodge. Situated on its own private lake, you will have everything you need to enjoy a blissful retreat with award winning country pubs such as The Dog & Pickle only a walk away. Please note: 1. We are strictly a minimum of two night stays. 2. We can only accept infants under 6 months old. 3. There is no swimming or paddle boarding allowed in the lake. NEW FOR 2026 - The Wellness Deck Sauna, Cold Plunge & outdoor shower, ready for use now!

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, 35 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.

Top Guest favourite
A balcony view is captured through bi-fold glass doors, featuring a small round table and two folding chairs. A decorative pumpkin sits at the center, with panoramic sea views of the estuary and boats in the distance, framed by a serene sunset.
Condo in Southend-on-Sea
4.99 out of 5 average rating, 426 reviews

Estuary Views Penthouse with Private Parking

A Beachfront Coastal Retreat with private driveway parking & situated in the sort after area Thorpe Bay. Boasting unspoilt Panoramic Sea Views. Central to Blue Flag Beaches, 2 mins from award winning restaurants, superb location for coastal walks, watching the seabirds & a short walk to the longest Pier in the world. Re-Designed with Bi-Folding Glass doors, bringing the Outside Inside. Intricately Designed embracing tiny details that define our property for a Luxury & cosy stay.

Guest favourite
Home in Medway
4.94 out of 5 average rating, 106 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 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, 87 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.

Top Guest favourite
Bungalow in Kent
4.97 out of 5 average rating, 104 reviews

Luxury Spa Retreat: Sauna & Hot Tub

Escape to our exclusive gated spa retreat, nestled on 5.5 acres of serene countryside in picturesque Fawkham, Kent. This private and tranquil haven offers breathtaking views of rolling hills, perfect for relaxation. Unwind in the luxurious sauna, steam room, or hot tub, soaking in the peace after exploring local attractions. Just minutes from Brands Hatch, our retreat blends seclusion with convenience, your ultimate quiet getaway awaits.

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
4.94 out of 5 average rating, 203 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
Apartment in Medway
4.88 out of 5 average rating, 26 reviews

River View Apt w/ Parking + Balcony | Sleeps 4

Modern 1-bedroom apartment with stunning views, perfect for up to 4 guests. The bedroom features a comfy double bed and wardrobe, while the open-plan kitchen, dining, and living area offers a double sofa bed, Smart TV, Wi-Fi, and board games. Enjoy free parking and a bright, stylish space just a 1-minute walk from ASDA. Central location ideal for exploring, relaxing by the river, or working away from home.

Popular amenities for Cooling holiday rentals

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