At Bloom Stays, we’re delighted to be growing our collection of beautiful holiday cottages to let in East Sussex. Known for its rolling countryside, artistic towns, and dramatic coastline, East Sussex is the perfect destination for families, couples, and groups looking for a getaway with character – and some of the best weather in the UK. From the cobbled lanes of Rye to the open landscapes of the High Weald, our East Sussex cottages offer the ideal base to explore this charming corner of the South East.
Wealden Holiday Homes
Cart Lodge & Dairy Barn, Blackham
Beautifully renovated to provide a spacious holiday home for couples or families with little ones, the beautiful Cart Lodge (sleeps 4) in Blackham gives an air of space and tranquillity, further benefiting from stunning views over the surrounding countryside. A woodburner provides the ultimate in cosiness, while the well-equipped kitchen allows guests to cook up a storm – ideal for a self-catering staycation.
A touch more intimate, neighbouring Dairy Barn sleeps two, making it a fantastic option for couples or friends travelling together. With high, wooden beam ceilings, and all the wonderful features shared with Cart Lodge, this property also benefits from a hot tub that overlooks the Weald – perfect for those moments that call for a little more indulgence.
These properties can be booked singly or together (dependent on availability), where they make a great choice for multi-generational families or groups visiting the Wealden or Tunbridge Wells areas.
Badger, Deer & Stag Shepherds Huts, Hartfield
Tucked away in the woods of the High Weald Area of Outstanding Natural Beauty, these shepherds huts — Badger (sleeps 2), Deer (sleeps 2) and Stag (sleeps 4) — offer a peaceful escape for couples, solo travellers, or small families. Each hut has been individually styled, with cosy interiors, well-equipped kitchens, and outdoor decking (and, for Stag, a woodburning stove), with each shepherds hut suiting slightly different requirements. The surrounding woodland and winding lanes invite quiet walks at dawn or dusk, while the nearby market towns of Tunbridge Wells and Crowborough offer more bustle when you feel like it.
Bullfinches Barn, Eridge
Bullfinches Barn (sleeps 6) is a beautifully converted traditional barn, set in the heart of open farmland yet within easy reach of charming local villages and towns. With exposed beams, a vaulted ceiling, a large farmhouse-style kitchen and a cosy living room with a log-burner, it strikes a comfortable balance between elegance and rustic warmth. Outside, you’ll find a private patio and garden that’s set up for alfresco dining, while the surrounding fields invite afternoon ambles aplenty.
The Potting Shed & The Cow Shed, Blackham
Both neighbouring our much-loved Dairy Barn and Cart Lodge properties, The Potting Shed and The Cow Shed in Blackham are charming, self-catering holiday homes in a peaceful countryside setting, ideal for those looking to unwind in the High Weald Area of Outstanding Natural Beauty. While they each feature well-equipped kitchens, plush bedding and plenty of space to relax in, they have their own distinct characteristics: The Cow Shed having a lovely fenced patio, while The Potting Shed features a fabulous double-bath beneath a fairy-lit pergola – perfect for a soak under the stars.
Rye Holiday Homes
The Cot, Winchelsea Beach
Escape to the unspoilt charm of Winchelsea Beach at The Cot, a characterful cottage within walking distance from the sea. With space for up to six guests, this is a wonderful space for families and small groups, who can enjoy board games in the lounge, and the BBQ and fire pit outside. Its location provides guests with easy access to both countryside and coast: by day, wander the marshes and nature reserves around Rye, and by evening explore the town’s art galleries and old inns.
Chequer / Rye Townhouse, Rye
Set inside one of Rye’s most historic buildings (and that’s saying something!) Chequer is brimming with character, with well-designed interiors providing ample light and comfort. With seven bedrooms (sleeping a total of 16 guests) across four floors, guests may retreat to their own spaces at night, while the large drawing rooms and dining area have plenty of space to bring everyone together. Located right in the centre of Rye, this incredible home is ideally situated for guests wanting to make the most of the town’s many art galleries, shops, and taverns (including the famous Mermaid Inn), while the River Rother, Nature Reserve, and beaches are all just a short drive away.
Groups up to 10 may book Rye Townhouse – our smaller edition of Chequer.
The Garden Room, Beckley
A stylish, compact escape for two, The Garden Room is the ultimate East Sussex hideaway, located just a 10-minute drive from the cobbled streets of historic Rye. A former granary, its clever design combine cosy, soft-furnishings with functionality, a fully-equipped, modern kitchen providing everything you need for a self-catering break. Direct access to a private garden invites guests to fully slow down: look forward to morning coffee in the garden, a local bakery, then perhaps a coastal walk or a visit to nearby East Sussex towns. For those who want a romantic hideaway with ease of access to local life, this property is a true gem.
Wheelwrights Cottage, Staplecross
A romantic bolthole in the village of Staplecross in the Rother Valley, Wheelwrights Cottage is perfect for couples seeking a peaceful getaway. A charming example of old meets new, the cottage provides a homely retreat with all the modern comforts, such as under floor heating in the bathroom, and a Nespresso coffee machine in the kitchen. Sleeping up to five guests, it’s ideal for couples, families, and small groups, who can enjoy the many sights of nearby Rye, Bodiam, and Tenterden, or take this time to visit one of many vineyards in the area.
The Grain Store, Beckley
Tucked away in the picturesque countryside surrounding Rye, the contemporary conversion of The Grain Store (sleeps 2) benefits from miles of unspoilt landscapes and proximity to historic sites aplenty. With light-filled living spaces and a sumptuous king-size bed, it’s a joy to stay in, with its boutique-styling feeling particularly indulgent. Imagine treating yourself and your beau by starting the day with a fresh cup of coffee on the patio terrace, or finishing it with a home cooked meal and a glass of local Sussex wine, before retreating for a restful night’s sleep.
Pelsham Farm Cottage, Peasmarsh
One of the newest in our collection, Pelsham Farm Cottage (sleeps 8) blends rustic charm with modern comfort. Set in the tranquil countryside just a short drive from Rye, this holiday home features stunning interiors and a large, private garden, offering a true ‘home-from-home’ feel. Families or groups will appreciate the space and setting: wander from the cottage into the surrounding farmland, discover hidden lanes, explore the nearby Tillingham vineyard, enjoy a picnic or cycle ride, and then head into Rye or out to Camber Sands for a coastal treat.
Pelsham View, Peasmarsh
The beautiful shepherds hut at Pelsham View offers an intimate escape for two. With a log burner providing modern comforts, and bifold doors opening on to wide-open fields, it’s a place for slowing down and connecting with nature whatever season you’re in. From here, you’re also within a short drive from the windswept beaches at Camber Sands, the vineyard next door at Tillingham Vineyard, and the winding cobbled streets of Rye, which is itself full of independent galleries, cafés and historic charm. The countryside trails around the property run across the High Weald’s rolling farmland, making it perfect for wanderers, wine-lovers or simply a cosy break for two.
Uckfield holiday homes
Brook Lodge Farm, Isfield
Brook Lodge Farm offers a stylish rural retreat built with eco-credentials in mind, tucked into the farmed landscape of the Ouse Valley near the market town of Uckfield. Thoughtfully designed for comfort and community, its open-plan living and garden set-up make it a relaxing base for a sociable holiday for up to six guests. From the property, you can wander through the historic lanes around Isfield, step aboard the restored Isfield Station of the Sussex Lavender Line heritage railway, or head further afield to the coast, where Hastings, Eastbourne, and Brighton await with their vibrant piers and seaside ambience.
Masketts Barn, Nutley
For families, friends, or groups seeking space and character, Masketts Barn is a show-stopping barn conversion on the edge of the Ashdown Forest. With six bedrooms sleeping 13, rustic oak beams, a walled garden, hot-tub, tennis court and sweeping views across the South Downs, it’s ideal for lively gatherings and mixed-generation stays. When you’re ready to explore, you have the forest’s ancient woodland right outside your door, the quirky heritage of the nearby Bluebell Railway, and seaside escapes at Bexhill‑on‑Sea, Brighton and Eastbourne all within easy reach. Expect restful nights, country walks, cosy fires and look forward to the stunning sundowner golden hour that countryside breaks are made for.
Heathfield holiday homes
Springhill, Heathfield
Set amidst rolling countryside near Heathfield, Springhill is a spacious escape with ample room for family gatherings. Its stunning interiors are straight out of a magazine, giving the property a real boutique feel that’s perfect for both lounging and the obligatory photoshoot. With an expansive garden, generous kitchen and living space, and comfortable bedrooms, it suits guests seeking both freedom and comfort. Outside, you’ll find a private swimming pool accompanied by open fields, quiet tracks and views that stretch for miles – ideal for a morning yoga, long lazy breakfasts or evening drinks on the terrace. Adventure is also within reach: forest walks, historic villages and the South Downs’ edge are all accessible, making Springhill a balance between modernity, nature and ease.
Why choose Bloom Stays for your East Sussex getaway?
At Bloom Stays, we’re proud to offer a growing collection of remarkable holiday cottages across East Sussex, with something to suit every getaway. Families will love our spacious countryside homes, couples can escape to romantic boltholes, and groups can book large or neighbouring cottages for time away together. Many of our properties are dog-friendly too, so no one needs to be left behind. Best of all, our friendly team is based in the region, and is always on hand to share local recommendations.
Start planning your East Sussex holiday
From the cobbled streets of Rye to the tranquil beauty of the High Weald, our collection of holiday cottages in East Sussex is the perfect starting point for your next break. Whether you’re after a countryside barn conversion, a town house steeped in history, or a cosy shepherd hut hideaway, Bloom Stays has a holiday cottage to let in East Sussex for you.
Get in touch with our team on the phone 01227 903404, on email [email protected], or on WhatsApp. Whether you’re looking for advice on an upcoming trip, or simple want to chat about our East Sussex locations and local hotspots, feel free to get in touch.
