Rye Cottages
For an unforgettable Sussex holiday, head to the charming and timeless town of Rye. Wander around the picturesque cobbled streets with their medieval buildings, tea rooms, galleries and boutiques, and uncover the fascinating tales of Rye's smuggling history. Read more
History-lovers will enjoy a visit to St Mary's Church and Rye Castle Museum, and Bodiam Castle is just a short drive away. Explore the charm of East Sussex, where you can head to the seaside for a trip to the pretty beach of Camber Sands, uncover fascinating history and heritage at nearby Battle, and enjoy an idyllic afternoon at an award-winning vineyard.
Our exclusive ferry discounts will make your island trip with Classic plain sailing.
We have 11 self catering cottages in Rye to show you...
7 nights from £490
4 Church Square
55201 bedroom, dog friendly self catering cottage in Rye.
Welcome to this gorgeous Grade II Listed cottage situated along one of Rye's famous cobbled streets, perfect for couples looking to stay in the heart of Rye. As you enter this ...
7 nights from £490
7 nights from £448
Hayesland Lodge
57001 bedroom, dog friendly self catering cottage near Rye.
This gem is situated in a peaceful and tranquil setting in a National Landscape (an Area of Outstanding Natural Beauty) with farmland views, a short drive from the coast and the me...
7 nights from £448
7 nights from £391
The Little Lodge
55991 bedroom, dog friendly self catering cottage near Rye.
This peaceful retreat for two is nestled in an Area of Outstanding Natural Beauty, near the village of Broad Oak and a short drive from the medieval town of Rye, Battle and the bea...
7 nights from £391
7 nights from £631
4 Roberts Row
48232 bedroom, dog friendly self catering cottage near Rye.
4 Roberts Row is a delightful cottage bursting with character, situated in the small hamlet of Beckley with easy access to the popular town of Rye. This beautiful terraced cotta...
7 nights from £631
7 nights from £494
Darjeeling Lodge
55982 bedroom, dog friendly self catering cottage near Rye.
If you're looking for a peaceful or romantic break in the heart of the Sussex countryside, then this is the place for you! Situated in Beckley, near the village of Broak Oak, Darje...
7 nights from £494
7 nights from £480
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 £480
7 nights from £1295
Luffs Farm
56535 bedroom, dog friendly self catering cottage near Battle.
This delightful farmhouse situated in 1066 country, has views over the valley towards the village of Sedlescombe. It makes an excellent retreat for families and friends looking for...
7 nights from £1295
7 nights from £563
Castlemans Stables West
44222 bedroom, dog-friendly self-catering cottage near Battle.
Set within the High Weald Area of Outstanding Natural Beauty, in the heart of East Sussex's 1066 countryside, Castlemans Stables West is one of a pair of sympathetically converted ...
7 nights from £563
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £1058
Castlemans Coach House
51244 bedroom self catering cottage near Battle.
In the heart of 1066 country and within walking distance of the pretty village of Sedlescombe, this former coach house is the perfect place for families and friends looking for a l...
7 nights from £1058
7 nights from £563
Castlemans Stables East
44212 bedroom, dog-friendly self-catering cottage near Battle.
In the heart of East Sussex's 1066 countryside and set within the High Weald Area of Outstanding Natural Beauty, Castlemans Stables East is one of a pair of sympathetically convert...
7 nights from £563
