Holiday houses in Playden

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Top-rated holiday rentals in Playden

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Top Guest favourite
Home in Rye
4.89 out of 5 average rating, 337 reviews

Wish Ward Cottage (Centre of Rye) 4 plus 2

Wish Ward Cottage is a beautifully refurbished 19th-century cottage in the heart of Rye, just off Mermaid Street. Perfect for families, couples or small groups, it blends historic charm with modern comfort. The kitchen / dining area open through French doors onto a private sunny courtyard, ideal for relaxed breakfasts or evening drinks. A cosy lounge offers space to unwind, with Sonos, Smart TV, Netflix and iPlayer throughout your stay. Just minutes from Rye’s shops, restaurants and Camber Sands

Top Guest favourite
An outdoor decking area features a white dining table with matching chairs, complemented by a bottle of champagne and glassware arranged on the table. Sunshine casts a patterned shadow across the space, surrounded by brick walls and potted plants.
Apartment in Rye
4.95 out of 5 average rating, 239 reviews

Ye Olde Cobbler - 1 Bedroom Flat for Rental in Rye

Ye Olde Cobbler - 1 Bedroom Flat for Rental in Rye. Central location in the heart of Rye just off of the high street. With an outdoor decking area, you can enjoy the peaceful town on your own little sun trap! Double bedroom with wardrobe, dressing table and full length mirror. Living room boasting two double seater sofas and a smart TV for your viewing. Fully equipped kitchen with an added dishwasher for your comfort. Full size bath with overhead shower in the bathroom to help you fully relax!

Top Guest favourite
A stylish entryway showcases a vintage poster for 'The Danny LaRue Show' on the wall, paired with a mid-century sideboard accented by decorative items. The staircase leads towards the living space, while a textured area rug adds warmth to the contemporary design.
Home in Rye
4.9 out of 5 average rating, 119 reviews

The Playhouse | Sleeps 2 | Rye | East Sussex

This unique property sits behind one of Rye's most iconic High Street shops. Tucked behind the main drag this architecturally important building has been completely restored and renovated. Offering a truly spectacular bolt hole from the demands of modern life but with all the mod cons. The Playhouse (one bedroom) is home to the quirky finds of its delightful owners, with an eye for colour, modern comforts, mixed in with playful vintage signs it creates a fabulous spot from which to explore.

Guest favourite
A charming cottage displays a wooden shingle exterior with a distinctive green door. The two-story structure features multiple windows, inviting natural light. The well-maintained facade is complemented by a cobblestone pathway, reflecting the historic character of its surroundings.
Cottage in Rye
4.95 out of 5 average rating, 144 reviews

23 Tower St., Landgate Cottage, Rye

Landgate Cottage is ideally located, opposite the remaining 14th Century Landgate entrance to the old citadel in the heart of Rye. Everything is nearby, with shops, tea rooms, bistros, pubs, restaurants and the Kino Rye cinema also. There is fantastic access to coast and countryside. Close to car parks (£3.00 / 24 hrs), bus stops and Rye railway station (London St Pancras is an hour and 4 mins). Two double bedrooms, bath, shower, fully equipped kitchen and outside terrace with seating.

Guest favourite
A spacious living area features large windows that frame captivating sea views. A wooden dining table is set between the windows, accompanied by two chairs. A plant is placed on each side of the room, and simple furnishings are styled for a relaxed atmosphere.
Apartment in Hastings
4.99 out of 5 average rating, 175 reviews

Escape to the Sea

Gorgeous, spacious, south-facing flat with stunning sea views, original features, and high ceilings. The sunrises/sets and moon reflections are breathtaking! In between St Leonards on Sea and Hastings, and 30 seconds to the beach! The bedroom has a king size bed and the living room a double sofabed. Bedding is cotton/linen washed with non toxic products. Flat is on the 3rd floor but not that many stairs and as such, sea views far from the madding crowd! There is free parking nearby

Guest favourite
The living room features a flat-screen TV on a dark stand, accompanied by a clear desk and a wooden chair. A small bar-style table for two is positioned near the window, adorned with floral artwork and a vase. Natural light enters through the window, illuminating the space.
Condo in Rye
4.96 out of 5 average rating, 613 reviews

Wheelwrights Rye

Wheelwrights is a luxury 1 bedroom apartment which is finished to a very high standard and comes complete with a balcony overlooking the Strand Quay, in Rye, East Sussex. The railway station, pubs, shops, restaurants & supermarket are all within a 5 minute walk. Rye Harbour, Winchelsea & Camber Beaches, 10 mins by car. Free WiFi Milk/Tea/Coffee/Bottled Water Breakfast Included on Saturday & Sunday 🍳 Two car parks situated next to us. £5 & £7 for 24 hours.

Guest favourite
The retreat's exterior is characterized by modern architecture, featuring large arched windows and a welcoming entrance. Surrounding greenery, including tall trees, enhances the natural setting, while a gravel pathway leads to a spacious outdoor area with wooden seating and potted plants.
Cabin in East Sussex
4.95 out of 5 average rating, 214 reviews

Relaxing Luxury Retreat

Hop Pickers Retreat is found in the heart of an Area of Outstanding Natural Beauty (AONB) on the Kent and East Sussex border. Located on an farm you are surrounded by wildlife, birdsong, mooing cows, stunning views and in the summertime the sound of a combine, combining the crops in the surrounding fields. It is the ideal place to turn off that phone and unwind with your glass of your favourite tipple in the woodfired hot tub underneath the big starry sky.

Top Guest favourite
A cobbled street lined with traditional timber-framed houses showcases the architectural charm of the area. The buildings feature decorative leaded glass windows and steep roofs, with greenery and street lamps adding to the historic ambiance. A clear sky can be seen above.
Home in Rye
4.98 out of 5 average rating, 237 reviews

14th-Century House in Rye's Historic Citadel

Hucksteps is a medieval, 3 bedroom/2 bathroom house centrally located in the Citadel of Rye. Facing St Mary’s Church, the house is surrounded by cobbled streets, period architecture, literary associations, stunning coastline, and vibrant culture. Camber's sandy beaches and dunes are an easy walk/cycle/drive away. A High Street full of independent shops, restaurants, inns, art galleries, Kino cinema, Rye Spa Retreat, tea rooms are round the cobbly corner.

Top Guest favourite
The historic windmill features a distinctive white weatherboard structure, surrounded by lush greenery. Two teak steamer chairs are positioned in the foreground, inviting relaxation in the garden. A clear blue sky with soft clouds enhances the serene rural setting.
Windmill in Benenden
4.99 out of 5 average rating, 879 reviews

Old Smock Windmill in rural Kent

Old Smock Mill is a romantic place for couples. The atmosphere inside is peaceful and relaxing. Everything is designed to unwind you from the moment you walk in. It is surrounded by the lovely Kent countryside where you can ramble and refresh yourselves by perhaps ending the day in one of the great pubs cosy by a log fire in Winter or in Summer in an English garden. Guests have said how hard it is to tear themselves away, it truly is a treasure to find.

Top Guest favourite
A charming view of Mermaid Street is captured, showcasing an array of historic buildings with black and white exteriors. Cobblestone paths wind through the scene, accompanied by neatly trimmed hedges and planters. A decorative sign hangs above, adding character to the quaint street.
Condo in Rye
4.95 out of 5 average rating, 378 reviews

Grade II listed apartment in Mermaid Street, Rye

A grade II listed apartment in the centre of Rye. The property is situated at the bottom of famous cobbled Mermaid Street through a courtyard entrance on The Mint. It is a short walk to local pubs, restaurants and fish and chip shops with beaches within a 10 minute drive. The property features a quirky steep winded staircase and is set on 3 floors! These are also super steep so please be careful with children. A 10 minute walk from Rye station.

Top Guest favourite
A charming bedroom is highlighted by a striped headboard adorned with decorative pillows. An accented wall in warm tones complements framed artwork above the bed. A small tray table holds a vase with fresh flowers, adding a touch of color and elegance to the space.
Home in Rye
4.99 out of 5 average rating, 180 reviews

The Yard Rye

The Yard is a two-bed interior-designed cottage in the citadel of the beautiful Cinque Port town of Rye. It is situated down a cobbled passageway next to a pretty tea room. PLEASE NOTE – The property can sleep up to two adults in the master bedroom and one child in the single, with a pull-out camp bed if needed for an extra child. We also have a travel cot for an infant. Please be aware we have a steep staircase.

Guest favourite
A stylish lounge bedroom features a king size bed adorned with a floral patterned duvet and plush pillows. A navy throw blanket is neatly placed at the foot of the bed. The room's walls are painted in a deep blue, and a wall clock is visible.
Condo in Rye
4.96 out of 5 average rating, 446 reviews

Beautiful boutique studio flat in town centre

Enjoy a stylish experience at this centrally-located place. This newly finished studio flat with fully furnished kitchen and dining area is in the centre of Medieval Rye, making it the perfect base to explore the historic Sussex south coast. This is a new property for us, however we are established hosts with super host status. Please do message if you have any questions. We’d love to hear from you.

Popular amenities for Playden holiday rentals