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 1010 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 1010 cottages available for May half term
7 nights from £1468 booking fees included
Island Cottage
61963 bedroom cottage with sea views in Bigbury-on-Sea, South Devon.
Welcome to Island Cottage, nestled in the sought-after village of Bigbury-on-Sea, its elevated location provides beautiful views of both Bigbury beach, Bantham beach and the iconic...
7 nights from £1468
From £103 per night + £53 booking fees
Paloma
6187Converted horsebox with outdoor bath near Malmesbury.
Set in serene countryside near the Cotswolds, Paloma, a beautifully converted vintage horsebox, invites you to truly switch off and enjoy a peaceful break. Leave the daily rout...
From £103 per night
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £1460 booking fees included
1 South Terrace
61623 bedroom, dog friendly cottage with sea views in Penzance, Cornwall.
Wake up to the sound of the sea, breathe in the salty air and experience one of Penzance’s most enviable locations. Perfectly positioned overlooking the seafront and iconic promena...
7 nights from £1460
7 nights from £857 * booking fees included
Woonsmith
61922 bedroom, dog friendly holiday cottage near Penzance, West Cornwall.
Escape to the peace and allure of the Cornish countryside at this beautifully renovated two bedroom cottage with its secluded, exclusive wild swimming lake just outside the pretty ...
7 nights from £857 *
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £740 * booking fees included
Admiral's Den
61692 bedroom, dog friendly apartment near the beach in Penzance.
Step into a piece of Cornish history at Admiral’s Den, a two-bedroom apartment occupying a wing of the magnificent Grade II Listed Georgian Nancealverne House. Set within 25 acres ...
7 nights from £740 *
7 nights from £756 booking fees included
The Old Tractor Shed
61802 bedroom, dog friendly self catering cottage near Winchelsea.
Tucked away on a working sheep farm close to the coast and the medieval towns of Rye and Winchelsea, this peaceful escape is surrounded by beautiful farmland and scenic footpaths i...
7 nights from £756
Nancealverne Estate
7 nights from £1613.19 booking fees included
7 nights from £873 * booking fees included
Apple Loft Cottage
61682 bedroom, dog friendly cottage near the beach in Penzance, Cornwall.
Nestled within 25 acres of enchanting grounds of historic Nancealverne House, Apple Loft Cottage is a beautifully restored property offering a peaceful stay steeped in centuries of...
7 nights from £873 *
7 nights from £1021 * booking fees included
Lavender Cottage
61762 bedroom, dog friendly cottage near the beach in Christchurch.
Lavender Cottage is a delightful two bedroom home with open plan living areas and wonderful outdoor space. Set in the exclusive Wick Village it is just a short walk from one of Dor...
7 nights from £1021 *
-
20% off
24 Jul 2026 - 31 Jul 2026
From £1148.60 £931.48 booking fees included
-
20% off
31 Jul 2026 - 7 Aug 2026
From £1148.60 £931.48 booking fees included
-
20% off
7 Aug 2026 - 14 Aug 2026
From £1148.60 £931.48 booking fees included
-
20% off
14 Aug 2026 - 21 Aug 2026
From £1148.60 £931.48 booking fees included
7 nights from £853 * booking fees included
Primrose Cottage
61792 bedroom, dog friendly self catering cottage in Bridport, Dorset.
Primrose Cottage is the quintessential Dorset coastal property with its pretty village location and gorgeous, enclosed garden - it is packed with character. This semi-detached two ...
7 nights from £853 *
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
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.
