May Dartmoor Cottages
Discover and rediscover Dartmoor this May. With the moors bursting into life, awash with colour and bathed in warm sunlight, there has never been a better time to make the most of a Dartmoor getaway. Enjoying a pick up in pace with local events and activities yet quieter ahead of summer, enjoy a May holiday in Dartmoor and do as little or as much as you like. Our holiday cottages provide a real home-from-home. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.Discover our May collection of 24 available Dartmoor cottages
Greenawell Farm Cottages
7 nights from £1836
7 nights from £878
The Granary
60102 bedroom self catering cottage near Moretonhampstead, South Devon.
If it's a superb rural retreat you are looking for, look no further, The Granary at Greenawell Farm is the perfect package. The Granary is a beautiful stone cottage, finished to an...
7 nights from £878
From £93 per night
Olive
5755Shepherds hut with wood-fired outdoor bathtub in South Devon.
Nestled in a tranquil meadow on the edge of Dartmoor National Park, Olive is a charming shepherd's hut, perfect for blissful days and star gazing nights surrounded by nature. For t...
From £93 per night
7 nights from £494
Horseshoe Cottage
57472 bedroom self catering cottage near Moretonhampstead, Dartmoor.
Welcoming a true Dartmoor gem! This charming semi-detached stone cottage nestles neatly within the grounds of Greenawell Farm, boasting oodles of space, homely touches, and a fabul...
7 nights from £494
7 nights from £1283 *
Rydon
55053 bedroom, dog friendly cottage near Bovey Tracey, South Devon.
Introducing Rydon, a 15th Century barn which has been restored and crafted into this most luxurious and comfortable retreat. This 'once upon a time' flower store has been architect...
7 nights from £1283 *
7 nights from £464
Stable Cottage
54461 bedroom self catering cottage near Moretonhampstead, Dartmoor.
Welcome to Stable Cottage! This gem of a cottage is part of a converted courtyard of traditional stone farm buildings and nestles perfectly within the picturesque Greenawell Farm ...
7 nights from £464
7 nights from £758 *
The Swallows
52943 bedroom, dog friendly holiday cottage near Chagford, Dartmoor.
The Swallows, a fabulous rural retreat awaits. Nestled in the most picturesque countryside, surrounded by the most special sights and sounds mother nature can offer, along with bei...
7 nights from £758 *
From £93 per night
Nellie's Nook
5348Dog friendly shepherds hut with wood-fired outdoor bathtub.
Welcome to Nellie's Nook, a delightful little hideaway nestled in a secluded spot close to Dartmoor National Park. Ideal for that romantic escape for two, or a tranquil solo getawa...
From £93 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 £789 *
Pulborough House
52564 bedroom, dog friendly holiday cottage near Tavistock, Dartmoor.
Welcome to Pulborough House, a lovingly restored detached white farmhouse in the centre of the much sought-after village of Lydford, including Devon Pub of the Year 2024, The Castl...
7 nights from £789 *
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15% off
19 Sep 2025 - 26 Sep 2025
From £625.00 £531.25
7 nights from £498
Little Oaks
49782 bedroom self catering cottage near Tavistock, Dartmoor.
Welcome to Little Oaks, a tranquil single-storey getaway nestled on the western edge of the majestic Dartmoor National Park. Its wonderfully peaceful location means this is an idyl...
7 nights from £498
Indulge in some much-needed downtime and head to Dartmoor this May. If you're looking for somewhere interesting to spend half term with the kids, Dartmoor provides lots of places to explore, as well as great access to nearby towns and cities. Perhaps you'd like to enjoy a romantic short-break over a May bank holiday with your loved one. If so, we have beautiful one and two bedroom properties, offering ample space and ultimate comfort during your stay. If walking is your thing, then Dartmoor is definitely the place for you. There are lots of stunning sights to be seen, including a chance to see the majestic Dartmoor ponies roaming free. If you've got a dog, then our dog-friendly properties in Dartmoor will definitely be of interest to you.
Self-Catering Cottages in Dartmoor for May
However you'd like to spend your holiday in Dartmoor, our cottages provide the comforts of a real home with luxurious modern touches. Whether you're a seasoned regular or first-time visitor, Dartmoor offers plenty to fall in love with over and over again. Choose from our 24 available cottages in May and take your first step on a journey to remember.
At Classic Cottages we pride ourselves on marketing only the finest quality self-catering cottages. Each of our cottages is handpicked; personally inspected and fully equipped for your total ease and comfort.
