An octagonal, stone-built toll house shaded by trees.

Book Self-Catering Holidays in Quirky and Unusual Holiday Homes

Fancy a holiday that’s a bit off-kilter, a self-catering holiday in a quirky and unusual holiday property? Who wouldn’t say no to a holiday with friends in a luxury lighthouse or a beautifully restored Napoleonic Fort?

Step into the delightfully eccentric world of quirky holiday cottages, where the ordinary takes a back seat and the extraordinary becomes your temporary abode!

Search here to find architecturally unique holiday cottages for a more than usually memorable holiday with family or friends.

The UK has a splendid choice of distinctive and unusual character cottages appealing to those looking for something slightly different from a traditional house. 

While quirky cottages are not the ‘everyday’ holiday property, they still offer the same standards, facilities, and amenities you would expect to find in any decent holiday property worth its salt.

View this collection of distinctive holiday properties to find one with that ‘must-stay’ funky factor for a long holiday or just a weekend break.

The tower of a windmill (no sails) surrounded by a shrub-filled garden.
Sleeps
6
Bedrooms
3

Once a working flour mill for over 100 years, Aylsham Windmill now offers luxurious, family-friendly self-catering holidays (with Wi-Fi) for 2-6 guests in Aylsham, a picturesque rural market town in North Norfolk midway between Norwich and the coast at Cromer.

  • Active Holidays
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  • Coastal Cottages
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A remote stone-built shooting lodge nestles in the lee of a Scottish mountainside.
Sleeps
8
Bedrooms
4

Luxury accommodation meets peaceful isolation at the wonderful Glenuaig Lodge, a dog-friendly, large and remote four-bedroom self-catering cottage for eight guests in the heart of the Glencarron Estate near Strathcarron. The Lodge enjoys beautiful views and is accessible by 4-wheel drive vehicles.

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Exterior of a Cotswold honey-stone cottage overlooking a small lawn and patio with a dining table.
Sleeps
3
Bedrooms
2

Laburnum Cottage is a charming and well-maintained country cottage in the picturesque Worcestershire village of Broadway. Surrounded by beautiful countryside, this lovely Cotswold holiday home boasts a mature private garden and can accommodate up to three guests in two double bedrooms. It's an ideal choice for anyone looking to escape to the tranquil countryside for a relaxing break. The property also features private parking and is dog-friendly, perfect for guests who want to bring their furry friends along on their holiday.

  • Accessible By Train
  • Active Holidays
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A grand 3-storey, brick-built Tudor house overlooks a large, formal lawned gardens.
Sleeps
6
Bedrooms
12

Surround yourself with royal luxury at Upton Cressett Hall, a grand regal cottage in Shropshire. Marvel at the manicured grounds of the pet-friendly cottage, and indulge in the seclusion and beauty of a residence boasting log fires, exposed beams, antique furnishings and unique décor.

  • Active Holidays
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A steam-train passes by a line-side holiday cottage on a sunny summer's day.
Sleeps
6
Bedrooms
3

Located near Woolston in Somerset, Railway Cottage is a picturesque destination for steam railway enthusiasts. This pet-friendly cottage on the West Somerset Railway boasts stunning countryside views, charming interiors, a cosy log burner, bright and airy rooms, oak flooring, and modern amenities. It has also earned a 4-star gold rating.

  • Accessible By Train
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  • Short Breaks
  • Walking Holidays
Two shepherd huts at dusk, converted and linked to form a single unit.
Sleeps
2
Bedrooms
1

Anne’s Hut blends into the surrounding woodland. The unique former shepherd’s hut has been fashioned into a romantic holiday cottage in Penterry, Monmouthshire, which boasts extensive gardens with wonderful countryside views, luxurious décor, a wood burner, an outdoor firepit and contemporary comforts.

  • Active Holidays
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A mock Shropshire castle on a small hillock surrounded by a stone wall and open fields.
Sleeps
4
Bedrooms
3

Sham Castle is a beautiful waterside cottage located near the village of Acton Burnell in Shropshire. With three bedrooms, it offers stunning views of the lake and is surrounded by lovely gardens. The cottage sits atop a rocky knoll and boasts original quarry tile floors. The drawing room features oak floors and arched windows, providing a perfect view of the serene surroundings

  • Active Holidays
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Exterior of a lighthouse holiday cottage and small tower on a grassy clifftop
Sleeps
2
Bedrooms
1

Panoramic ocean views stretch before The Link, a romantic cottage set in Cromer Lighthouse beside the golf course on the Norfolk coast. White walls and luxurious contemporary décor complement the setting, while the enclosed garden offers another space to enjoy the views and the clean sea air.

  • Active Holidays
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  • Coastal Cottages
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  • Small Cottages
  • Walking Holidays
  • Waterside Cottages
Aerial view of a tall, brick-built, twin-towered, Victorian folly in a rural location.
Sleeps
2
Bedrooms
1

The Ultimate Romantic Bolthole for Couples in the Shropshire Countryside.

The Summer House is a Grade II listed octagonal tower and summer house built around 1607 near the Shropshire village of Eyton-on-Severn. The memorable, romantic rural retreat will entice couples with its spiral staircase, original features, elegance, magnificent rural views, and a wood-burning stove in the bedroom

  • Active Holidays
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  • Luxury Holiday Cottages
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  • Romantic Cottages
  • Small Cottages
  • Walking Holidays

Whimsical Wonders: Quirky Holiday Cottages for the Adventurous Soul

Fancy a holiday that's a bit off-kilter? Step into the delightfully eccentric world of quirky holiday cottages, where the ordinary takes a back seat and the extraordinary becomes your temporary abode!

A Spin on Traditional Stays

Imagine waking up in a windmill, your head literally in the clouds (well, almost). These cylindrical charmers offer a slice of the high life, complete with winding staircases and panoramic views that'll make your Instagram followers green with envy.

Experience the Whimsical Beauty of Converted Railway Cottages

Or how about channelling your inner conductor in a converted railway carriage? All aboard the nostalgia express! These compact cottages are just the ticket for those who love to choo-choose unique accommodations.

Lighthouse Living: Not Just for Lonely Keepers

Lighthouse cottages are a beacon of hope for those who prefer their holidays with a dash of maritime magic. Fall asleep to the rhythm of crashing waves and wake up to views that'll make you feel like the king (or queen) of the sea.

Elevated Experiences

Tree huggers, rejoice! Luxury treehouses offer a chance to live out your childhood dreams, minus the splinters and wobbly planks. These lofty retreats come with all the mod cons, proving that the high life doesn't have to mean roughing it.

Fantasy Becomes Reality

Hobbit holes aren't just for the vertically challenged or Middle-earth enthusiasts. These earth-covered dwellings offer a chance to burrow into comfort, with round doors that would make Bilbo Baggins proud.

Signalling a New Kind of Stay

For a truly on-track holiday, converted signal boxes offer a unique vantage point. These elevated abodes give you a bird' s-eye view of the surrounding landscape, without needing actual wings.

Rustic Charm in a Compact Package

Shepherd's huts prove that good things come in small packages. These snug sanctuaries offer a cosy retreat that's perfect for those looking to count sheep in more ways than one.

Architectural Oddities

Follies, those wonderfully whimsical structures built purely for decoration, now offer more than just eye candy. Stay in a mock castle or a miniature Greek temple and live out your architectural fantasies.

These unusual holiday homes are more than just a place to rest your head; they're the starring characters in your next great adventure story. Whether you're planning a romantic getaway, a family escapade, or a solo sojourn, there's a quirky cottage waiting to become the backdrop to your holiday memories.

Ready to embark on your own distinctive holiday adventure? Explore our curated selection of quirky holiday cottages and unearth the perfect unconventional abode for your next getaway. From quirky cottages to unusual holiday homes, we offer a smorgasbord of properties that are anything but ordinary. Book directly with property owners and dive into a world of unique stays across the UK, enjoying transparent pricing and a personalised booking experience.

Your extraordinary holiday begins here. Uncover your ideal quirky cottage today and enter a world where the unusual becomes the unforgettable!