Cottages For May in South England
Shhh! Don’t tell too many people this but, if you’re looking for a cottage holiday in May you might have stumbled on one of the best months to visit South EnglandRead more
Spring is in full swing, it is often one of our sunniest months and some of the best local festivals start. And you get the pick of the properties in South England. So have a look through our 142 holiday cottages available this May in South England.
Our exclusive ferry discounts will make your island trip with Classic plain sailing.
We have 142 self catering cottages available to rent in May in South England
7 nights from £643
Weald View Cottage
52842 bedroom self catering cottage near Maidstone.
Perfectly situated in the heart of the Kent countryside, this pretty semi-detached cottage with spectacular views across the Kent Weald is ideally located for walkers, couples and ...
7 nights from £643
Dovecote Garden
7 nights from £1407
We are Gold accredited with the Green Tourism Business Scheme.
Green Tourism Business Scheme
As a company, we look across our business and try to make sustainable changes and decisions. From using recycled paper in our printers to putting in measures for using less energy in our offices, we keep an eye on our impact on the environment.
Beyond our offices, we have passed on the same ethics to our holiday cottage owners by setting up our own Green Scheme that they can join. Each property has to tick off a certain number of actions to be included in the scheme, many of which go above and beyond the GTBS requirements.
From £131 per night
Little Oak Treehouse
5288Gorgeous dog friendly treehouse with a wood burner near Pulborough.
This gorgeous quirky treehouse situated just two hours from London, is the perfect escape for a romantic getaway. Truly unique and in a lovely part of West Sussex, it sits in a sec...
From £131 per night
From £91 per night
Cala Lily
5289Dog friendly shepherds hut near Pulborough.
With countryside views and just two hours from London, Cala Lily is a luxury shepherd's hut situated in the beautiful countryside of West Sussex and offers a dreamy escape where yo...
From £91 per night
From £91 per night
Douglas Fir
5290Dog friendly shepherds hut near Pulborough.
Hidden away in the West Sussex countryside yet just two hours from London, this luxury shepherd's hut offers a magical escape for two. Beautiful and handcrafted, it has all you ...
From £91 per night
7 nights from £551
Berry Cabin
52862 bedroom, dog friendly, bolthole in Seaview, Isle of Wight.
What a little cutie! Berry Cabin is a delightful bolthole for four guests and one well behaved doggy looking for some summer fun! Surrounded by Hersey nature reserve and countrysid...
7 nights from £551
7 nights from £570
Reysons Barn
52852 bedroom thatched self catering cottage near Rye.
Reysons Barn is perfect for couples and families who are looking for a rural escape in East Sussex. Converted in 2009, this lovely thatched barn sits on the edge of a small orchard...
7 nights from £570
From £79 per night
Jessie
5231Luxury dog friendly Shepherds Hut near Battle.
Jessie is a gorgeous shepherd's hut situated two hours from London, tucked away down a long meandering path in a paddock between crab apple and cherry trees, with views of the Suss...
From £79 per night
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.
7 nights from £1152
South Barn at Pickeridge
52113 bedroom, dog friendly self catering cottage near Haywards Heath.
South Barn at Pickeridge is tucked away on a 120 acre working farm in a secluded valley between West Hoathly and Ardingly. It's the perfect retreat for families and friends looking...
7 nights from £1152
7 nights from £1607 *
Newclose Houseboat
52004 bedroom houseboat with sea views in Bembridge, Isle of Wight
Welcome aboard Newclose Houseboat, a beautifully restored contemporary houseboat located in picturesque Bembridge harbour on the Isle of Wight, just a short stroll away from the st...
7 nights from £1607 *
