May Half Term Holiday Cottages
With a cool breeze and warm sunshine, May marks the start of summer and many happy times to come. Kick start your summer properly and hop in the car; a holiday in a luxury self-catering cottage awaits. Browse through our list of 944 available cottages and find your favourite. All of our cottages are handpicked; personally inspected and fully equipped so your holiday is the best it can be. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 944 cottages available for May half term
7 nights from £905 booking fees included
Box Cottage
62073 bedroom, dog friendly cottage near the beach in Croyde, Devon.
In the heart of the charming village of Georgeham, just two miles from the golden sands of Croyde Bay and one mile from beautiful Putsborough Beach, Box Cottage is perfectly placed...
7 nights from £905
From £230 per night + £53 booking fees
Ruska
6209Luxury cabin for two with an outdoor bath, privately nestled in the Forest of Dean.
Sitting in the Gloucestershire countryside, this lakeside retreat for two offers a peaceful and romantic getaway. This gorgeous cabin has been lovingly handcrafted with luxury in m...
From £230 per night
Reserve your 2027 holiday for just £40.00
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Ballacosney Cottage
219Stylish Laxey cottage with private gym and sauna
Tucked away up a peaceful lane above Laxey, Ballacosney Cottage is a beautifully renovated retreat designed with relaxing island stays in mind. Fresh, modern and filled with natura...
7 nights from £946 booking fees included
Rubena Cottage
62002 bedroom, dog friendly cottage near the beach in Port Isaac.
A mere hop, skip and a jump from the water's edge, this absolute gem of a cottage has been restored with exquisite care, creating a most desirable retreat that's perfect for warm s...
7 nights from £946
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Best company for UK holiday home rentals
7 nights from £990 booking fees included
St Peter's House
62022 bedroom self catering cottage in Gloucester.
Set within Gloucester Cathedral's grounds with a magnificent glimpse of the Cathedral spires from the impressive staircase, St Peter's House enjoys a truly amazing location. A hous...
7 nights from £990
7 nights from £1249 booking fees included
Hooper's House
62034 bedroom self catering cottage in Gloucester.
Hooper's House is a centuries-old property sitting in harmony with the historic buildings of Gloucester Cathedral but with a contemporary interior vibe, mixing traditional and mode...
7 nights from £1249
From £113 per night + £53 booking fees
Bottle Lodge
6206Grade II Listed, lovingly restored 1807 Bottle Lodge for two in Staffordshire.
Sitting in the Staffordshire countryside at the entrance to Tixall Estate, a unique and historic stay awaits at Bottle Lodge - named for its quirky octagonal shape that looks like ...
From £113 per night
7 nights from £838 booking fees included
Beau's Barn
61973 bedroom, dog friendly holiday cottage near Padstow, North Cornwall.
Escape the everyday with a well-deserved break at this rural retreat, nestled in the glorious Cornish countryside, yet only four miles from Padstow, Cornwall's culinary capital, an...
7 nights from £838
7 nights from £682 booking fees included
Hawcombe Cottage
62051 bedroom, dog friendly cottage with sea views near Tavistock.
Tucked away in the pretty riverside village of Bere Ferrers, Hawcombe Cottage is a charming hideaway for two, perfectly placed for those seeking a peaceful escape surrounded by the...
7 nights from £682
7 nights from £693 booking fees included
April Cottage
61992 bedroom, dog friendly cottage near the beach near Coverack.
Tucked away in an historic beachside location, this chic yet characterful semi-detached cottage has been lovingly restored and brought back to life, creating the perfect escape for...
7 nights from £693
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Spend your days exploring deep, green countryside and skim stones across lazy streams. Follow the scent of salty air and head to the coast, spending long days on the beach flitting between soft sands and cool sea. Perch on a bench and watch as life goes by, before heading to a local restaurant to dine on fresh, local produce lovingly crafted and prepared by skilled hands. Then, when you've had your fill of exploring, turn your attention to relaxing. Throw yourself into the holiday spirit and land in your own private self-catering cottage, primed and ready for you. An early summer break in your own slice of paradise can give you the chance to unwind, catch up and settle into a slower, more considered rhythm.
Spend your May-Half Term in a Luxury Retreat
Whether you are looking for a solo retreat or want to bring the whole family away for a much-needed break, May half term provides ample opportunity to escape to greener grass for a while. However you'd like to spend your time, our cottages offer wide variety and consistent quality. Many of our cottages are dog-friendly too, meaning everyone can join in this May half term.