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Set within the heart of Rye’s conservation area, Chequer is a striking double-fronted Georgian townhouse and one of the most recognisable homes in the town. Just moments from the cobbled streets, galleries, and independent shops, this beautifully restored Rye holiday home enjoys far-reaching views across the nature reserve towards Camber Sands.
Recently renovated over two years with the utmost care and attention to detail, the house balances its architectural heritage with a calm, contemporary finish – courtesy of local tradespeople, designers, artists and makers. High ceilings, sash windows, and original features sit alongside thoughtfully curated interiors, creating a space that feels both elegant and comfortable. Arranged across four floors, Chequer offers generous accommodation for group stays, with seven boutique-style bedrooms and a choice of reception rooms designed for gathering everyone together.
Whether sharing meals around the kitchen table, settling into the drawing rooms, or enjoying time on the terrace, every corner of this beautiful holiday home has been thoughtfully designed for enjoyment. At the same time, the scale of the house allows for quieter moments, with peaceful corners and elevated views adding to the sense of retreat.
With Rye’s restaurants, pubs, and cinema just around the corner, and the coastline within easy reach, Chequer is well placed for exploring both town and coast. Spacious, central, and full of character, it offers a refined base for group stays in one of Kent’s most sought-after destinations.
Select your dates to check availability
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Chequer: Sleeps 14 (plus 2 children on day beds on request at £75 per bed). 7 bedrooms, 6 bathrooms, 4 reception rooms, tiered terraces and an upper kitchen terrace/balcony.
Lower Ground Floor
Access is via the grand entrance hallway
Bedroom 1 (sleeps 2) King-size bed with hanging space, chest of drawers, and smart TV
Shower room with walk in shower, WC
Recreation area/kitchenette area with dishwasher, fridge/freezer, microwave, Nespresso (original) coffee machine, kettle
Access to the tiered terraces - terraces over three levels with an array of seating and relaxation areas
Ground Floor
Grand entrance hallway
Sitting room with sofa and armchair seating for 10 guests, large smart screen TV
Bedroom 2 (sleeps 2) King-size bed, smart screen TV, hanging space, chest of drawers. En suite shower room.
Morning reception room, ideal for early risers, a place for watching the sunrise. Fridge, Nespresso coffee machine (original). Sofa seating and window seats for 6-8 guests.
Utility room with washing machine and tumble dryer, bin store area
Shower room and WC (via utility area - great for washing muddy paws via the side access entrance)
First Floor
Drawing room with high sash windows with far reaching views. Sofa and casual seating for 10/12 guests. Ornamental fireplaces.
Open plan kitchen with electric oven, microwave oven, induction hob, American fridge with freezer draws, dishwasher, Ninja air fryer, Nespresso (original) coffee machine, (Wood burning stove - available by arrangement). Dresser full of dinnerware and crockery. A starter pack includes tea, coffee, fresh milk, butter, local loaf of bread and jam.
The dining area seats 10-12 comfortably with 4 more on an additional trestle table.
The kitchen opens onto a high line terrace area with seating for breakfast dining for 10. Perfect for lazy mornings.
Bedroom 3 (sleeps 2) King-size bed, built in wardrobes, chest of drawers
Shower room with walk in shower and WC
Second Floor
Bedroom 4 - Master bedroom (sleeps 2) Super king-size bed, smart TV, en suite shower room with slipper bath, walk in shower and double sink. Fold out bed available for 1 child upon prior request.
Bedroom 5 (sleeps 2 ) King-size bed, large wardrobe, dressing table. Fold out bed available for 1 child upon prior request.
Bedroom 6 (sleeps 2) King-size bed, large wardrobe, chest of drawers
Bedroom 7 (sleeps 2) King-size bed, hanging space and chest of drawers
Bathroom with slipper bath, and walk in shower and basin.
n.b* Fold out day beds (max of two) are available for children under 10 only with bedding and towels supplied. Supplement of £75 per bed. Must be booked in advance (no later than 7 days before arrival)
Outside
Rear terraces on three levels with occasional seating (4) and sunbeds.(5)
Services
Wi-Fi throughout (yet to be tested)
Central heating throughout and underfloor heating.
Sky Package available on TV.
Parking
There is a loading bay directly outside for 2 cars to drop off bags. In the near area 2 hours parking via paid metres or Ringo App can be used. Long stay parking is available a short walk away, closest is The Saltings. Rates may vary but at time of listing £10 per day. We will provide you with a list of parking areas around Rye for your convenience.
Trains and Access
Railway station - Rye is 5 minutes away on foot. Ashford International for direct access from London is with 30 minutes taxi drive.
Extras and Services
Bloom Stays offers a concierge service including a curated list of suppliers for catering, celebration planning, local produce tasting (cocktail making and wine tasting) massages and beauty treatments in the home and more. Please get in touch and let us know your plans.
Businesses
Looking to hold a delegates event? Chequer offers numerous places to break out from team meetings in the kitchen around the table, to break out rooms in three further receptions. On request services can be arranged for A boards and projectors. The Smart TVs can be connected to. Max numbers remain at 14.
Towels and linen provided
Wi-Fi
Sky package available on TV
Central heating throughout
Pets allowed, up to 2. Please note that additional pet charges are 35 pound per pet per week (or part of) will be charged.
No parking — there are a number of paid-for car parks within a short walk of the property. Information available on request. The drop-off zone is right outside. The Train station of Rye is within a 5-minute walk away and Ashford International 30-minute taxi drive.
The heart of the home is on the first floor. The ground floor entry level offers a TV lounge, as well as an accessible bedroom.
Early check in, and late checkouts, may be available on request, subject to availability. Fees will apply. Please contact Bloom Stays for more details.
If you're wondering how to feed your crowd on holiday, check out our local caterers page. We have a long list of recommended private chefs for brunches, lunches, BBQs and bespoke dinner parties.
Take the stress out of organising your celebration with bespoke event planners, My Event Concierge. From private dining and murder mystery parties to yoga, craft workshops, and even axe throwing, they'll match your group with trusted suppliers and create a tailored itinerary.
We hope you have a wonderful stay in Chequer, Rye. We would respectfully ask that the following house rules are adhered to, to avoid any damages to our beautiful holiday home. Should any damages arise please note charges may be taken from your security deposit.
Especially important when multiple groups are staying for nearby weddings please ensure all guests are aware of these rules. The key box should be managed for guests sharing access keys. Please take care not to lose the keys.
Tucked away in East Sussex, just a stone’s throw from the sea, Rye is a perfectly preserved medieval town with cobbled streets, crooked timber-framed houses, and sweeping views over the Romney Marsh. Once a coastal stronghold and smugglers’ haven, Rye is now a haven for foodies, families, and culture-lovers alike. The surrounding area is rich in wildlife, vineyards, wide open beaches, and rolling countryside, offering a little of everything for the curious traveller.
Explore the Ypres Tower (Rye Castle), a 13th-century fort offering insight into Rye’s rich past, complete with tales of smuggling, courtroom drama, and sweeping rooftop views over the town and coast. Dine on East Street, where historic charm meets modern flavours. The Union stands out for its locally sourced sharing plates and stylish setting in a centuries-old building. Visit Camber Sands, a vast golden beach just ten minutes from Rye. Ideal for families, it’s perfect for paddling, kite-flying, sand dunes, and seaside picnics.
Enjoy a relaxed tasting at Tillingham Vineyard in nearby Peasmarsh. This organic winery offers beautiful views, artisan wines, and a peaceful garden setting—great for both adults and children. Wander through Rye’s independent shops to discover antiques, vintage books, and handmade local goods—ideal for unique souvenirs and gifts. Rye is very accessible with trains from London and abroad via Ashford International and through to the town. Chequer is within walking distance of the station.
Yes. This holiday cottage in Rye allows two dogs at the holiday rental for the duration of your stay. Pets are charged at an additional 35 pounds per pet, per week.
Yes. Sleeping up to 14 guests across seven bedrooms and multiple reception rooms, Chequer is an excellent large group accommodation option for trips that include family gatherings and celebrations.
We recommend packing comfortable shoes for walking Rye’s cobbled streets, along with layers and beachwear if you plan to visit nearby Camber Sands or Winchelsea. The property also features a Nespresso coffee machine; if you wish to make use of this, Nespresso compatible pods can be purchased online or from local supermarkets.