Holiday houses in Isle of Sheppey

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Top-rated holiday rentals in Isle of Sheppey

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

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Top Guest favourite
Guesthouse in Minster on Sea
5.0 out of 5 average rating, 40 reviews

Tranquil Lodge – peaceful country stay by the sea

Tranquil Lodge is a private annexe beside our home in Minster-on-Sea, overlooking open fields where rabbits and horses are often spotted. Ideal for two (flexible for three), with a king bed and single sofa bed, plus baby items on request. Just a 10-minute walk to the cliffs + beach, with country and coastal walks from the door. Fully equipped kitchen, parking, garden, EV charging, vanity/desk, Wi-Fi + TV with Apple TV (guests sign into their own apps). A calm base for exploring Minster and Kent.

Top Guest favourite
Cabin in Biddenden
5.0 out of 5 average rating, 107 reviews

The Oaks. Beautiful Scandi style cabin on stilts

The Oaks cabin, a romantic escape from daily life - tranquil and luxurious. Relax from the moment you arrive. Nestled next to ancient woodland within a family small holding. Adjoining the High Weald National Landscape, 2 miles from Tenterden in the Kent countryside. From here you can enjoy wonderful experiences in Kent and Sussex and end your day in one of the great local pubs, breweries or vineyards. Immerse yourself in nature from the deck and adjoining field. A cabin of pure, sleek escapism.

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.
Guesthouse in Sittingbourne
4.93 out of 5 average rating, 302 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
A vibrant garden filled with blooming lavender plants is set against a serene landscape of lush greenery. Rows of fruit trees can be seen in the background, with a clear blue sky enhancing the tranquil scene.
Home in Teynham Street
5.0 out of 5 average rating, 125 reviews

Separate Studio near Faversham including Breakfast

One bedroom en suite studio with private entrance. Located in quiet country surroundings near fruit orchards. 3 miles from lovely market town of Faversham where there are numerous pubs/restaurants. Close to mainline railway with easy access to Kent coast and central London. 12 miles from historic Canterbury. The property is ideally located for walkers and is situated on Cycle Route no 1. 1 Mile from tranquil Conyer Marina & The Ship Inn 10 miles to the Michelin star restaurant, The Sportsman.

Guest favourite
A bright sleeping area is highlighted by a spacious bed with soft linens and neutral-colored accents. A kitchenette is visible in the background, alongside large glass doors that open to the garden. Natural light enhances the inviting and calm ambiance.
Cabin in Kent
4.91 out of 5 average rating, 201 reviews

The Mermaid Cabin- your secret Whitstable escape.

Tucked in a peaceful garden setting, this stylish & cosy petite cabin is ideal for a relaxing getaway. private entry far end of garden, fenced off decking space surrounded by greenery, Perfect for couples looking for a charming break in the quirky seaside town of Whitstable. The cabin is a 5-minute walk from the train station and 10 minutes to the beach and vibrant high street. You’ll be within easy reach of independent shops, cafés, wine bars & restaurants—everything you need for your stay.

Guest favourite
A charming wooden lodge is nestled among lush green trees, featuring a sloped roof and welcoming wooden deck. Large windows allow natural light to fill the interior, and the entrance opens directly into a spacious and inviting living area. Surrounding greenery enhances the tranquil setting.
Cabin in Wadhurst
4.98 out of 5 average rating, 136 reviews

Goldcrest Lodge Wadhurst

Goldcrest Lodge is a peaceful hideaway within secluded woods on the 140 acre historic estate of Wadhurst Castle. It is designed to blend in to its woodland setting, yet is bright and spacious with modern luxuries - perfect for a romantic break, a restful escape or for reconnecting with nature. It has a double bedroom (5' bed) with huge picture window, a central main room with sofa bed leading to a kitchen area and separate shower room beyond. Decking and private screened bath. Dog friendly.

Top Guest favourite
Apartment in Canterbury
4.98 out of 5 average rating, 332 reviews

Best Location! Top Ranked Riverside Gem | Parking

🥇 AWARDED TOP 1% OF HOMES 🥇 💫 Welcome to your ideal Canterbury retreat - a true home away from home! 🎯 Perfect for weekend escapes, long stays, contractors and also guests attending graduations. 🏆 Highly rated 🅿️ Free parking space 🚶‍♂️ Very short walk to centre 🚇 5 minute walk to west station ✨ Luxurious riverside apartment 📍 Located on the best side of town 2️⃣ Suitable for up to 2 guests + baby 🌺 Beside the iconic Westgate Gardens 🥣 Cereal, tea, coffee & pano chocolates

Guest favourite
Farm stay in Preston
4.86 out of 5 average rating, 152 reviews

The Midnight Express; Magical Bus, Hot Tub+ Views!

Probably the most magical bus stay in the UK, inspired by the romance of the Orient Express & Harry Potter ✨ Set in peaceful countryside near Canterbury, with epic views, the Midnight Express is a one-of-a-kind converted double-decker bus for couples, families, and small groups seeking a cosy, playful stay. With a hot tub, gaming area in the driver’s seat, cinema snug, log burner, private garden, and separate First Class Waiting Room, it feels like a magical little world of its own.

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, 436 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.

Top Guest favourite
The exterior of a historic brick building is showcased, featuring a colonnaded façade and decorative elements. The bright blue sky provides a contrasting backdrop, enhancing the building's architectural details and its distinguished presence along the high street.
Condo in Whitstable
4.99 out of 5 average rating, 361 reviews

Boutique apartment in the heart of Whitstable

Stunning 1-bedroom apartment in an historic brick fronted and colonnaded building constructed circa 1900 and once the high street bank. Located in the very heart of vibrant Whitstable, with all of its wonderful independent bars, microbreweries, roasteries/coffee shops, restaurants, boutiques and galleries. Only a short walk from the famous harbour and beaches of this boho seaside town and only an 8 minute walk from the station with direct services to London and Canterbury.

Superhost
An open living area features a modern gray sofa, sleek cabinetry, and a wall-mounted television. Large windows offer views of the surrounding landscape. The wooden flooring, designed in a herringbone pattern, complements the light wood paneling and cabinetry throughout the space.
Barn in Kent
4.86 out of 5 average rating, 124 reviews

Oak Lodge @ The Oaks Retreat

This memorable place is anything but ordinary. It is The Oaks Retreat, WINNER of the Paris Design awards 2024 'best hospitality interior', an architecturally inspired bespoke woodland Airbnb located in the seaside town of Whitstable. The Oak Lodge offers 2 king size bedrooms fully customized with high-end finishes which to need to be seen in person to be fully appreciated. Our Wellness area is equipped with a log burning sauna, a cold plunge and outdoor shower.

Top Guest favourite
The historic windmill features a distinctive white weatherboard structure, surrounded by lush greenery. Two teak steamer chairs are positioned in the foreground, inviting relaxation in the garden. A clear blue sky with soft clouds enhances the serene rural setting.
Windmill in Benenden
4.99 out of 5 average rating, 881 reviews

Old Smock Windmill in rural Kent

Old Smock Mill is a romantic place for couples. The atmosphere inside is peaceful and relaxing. Everything is designed to unwind you from the moment you walk in. It is surrounded by the lovely Kent countryside where you can ramble and refresh yourselves by perhaps ending the day in one of the great pubs cosy by a log fire in Winter or in Summer in an English garden. Guests have said how hard it is to tear themselves away, it truly is a treasure to find.

Popular amenities for Isle of Sheppey holiday rentals