Chequer
Rye, East Sussex
7
5
16
2
Beautiful Period Grandeur in the heart of Rye — where heritage meets urban luxury living. Perched proudly on East Street in the very centre of historic Rye, this exceptional three-storey Grade listed home offers an unparalleled stay for those seeking space, style, and something truly special. With sweeping views across the open expanse of the Romney Marsh all the way to the distant shimmer of the sea, this is not just a home — it’s a destination.
Inside, the property unfolds with effortless grandeur. Seven beautifully appointed, boutique hotel-inspired bedrooms and bathrooms provide serene sanctuaries for rest and retreat, while four elegant reception rooms offer a mix of refined comfort and entertaining space. Whether you’re gathering around the log burner in the kitchen whilst hosting a dinner, or having a summer soiree in the more formal drawing room, or spilling out onto the sunlit terraces with a glass of wine, every corner has been thoughtfully designed for both indulgence and relaxation. Spanning four generous levels, this grand home combines period character with modern luxury. Think high ceilings, large sash windows, original architectural details, and an understated yet sophisticated interior palette.
Catering and entertainment packages are available upon request, though with Rye’s acclaimed restaurants, cafés, and bars quite literally on your doorstep, you’ll be spoilt for choice without lifting a finger. Step outside to discover cobbled streets, boutique shops, art galleries, and coastal walks, all within minutes. Whether you’re celebrating, reconnecting, or simply escaping, this remarkable home is the perfect setting for unforgettable moments. A rare opportunity to stay in one of Rye’s most distinguished residences — where the views are endless and the welcome is second to none.
Inside, the property unfolds with effortless grandeur. Seven beautifully appointed, boutique hotel-inspired bedrooms and bathrooms provide serene sanctuaries for rest and retreat, while four elegant reception rooms offer a mix of refined comfort and entertaining space. Whether you’re gathering around the log burner in the kitchen whilst hosting a dinner, or having a summer soiree in the more formal drawing room, or spilling out onto the sunlit terraces with a glass of wine, every corner has been thoughtfully designed for both indulgence and relaxation. Spanning four generous levels, this grand home combines period character with modern luxury. Think high ceilings, large sash windows, original architectural details, and an understated yet sophisticated interior palette.
Catering and entertainment packages are available upon request, though with Rye’s acclaimed restaurants, cafés, and bars quite literally on your doorstep, you’ll be spoilt for choice without lifting a finger. Step outside to discover cobbled streets, boutique shops, art galleries, and coastal walks, all within minutes. Whether you’re celebrating, reconnecting, or simply escaping, this remarkable home is the perfect setting for unforgettable moments. A rare opportunity to stay in one of Rye’s most distinguished residences — where the views are endless and the welcome is second to none.
Check Availability & Book
Book Now
Select your dates to check availability
Selected Available Unavailable
-
Facilities
Board GamesChild FriendlyCoffee MachineCotDishwasher3 Miles To The Beach0.1 Miles To The PubHairdryerHighchairIron & BoardMicrowaveParking - On StreetPet FriendlySmoke DetectorsTumble DryerWashing MachineWi-Fi
About the House
7
5
16
2
Chequer, Rye, sleeps a max of 14 adults plus 2 more children on day beds.
Within 7 bedrooms, 5 bathrooms, 4 reception rooms, tiered terraces and an upper kitchen terrace. Games room area.
Living / Reception areas:
Ground Floor
Entering through into the grand hallway.
Sitting room / TV lounge, seating for 8 / 10 guests, large Smart screen TV, large sash windows.
Morning room, ideal for early risers, a place for watching the sunrise. Coffee machine, cups and items. Smart screen TV. Sofa seating and window seats for 6/8 guests.
Utility room, with washing machine and dryer, with the main bin store area
Shower room and WC (via utility area - great for washing muddy paws via the side access entrance.
Lower ground floor access is via the grand hall way:
Games room / Evening area with Large Smart TV, dart board, fusbol table. Kitchenette with fridge and freezer, coffee machine, microwave, popcorn maker, host of plastic ware for the tiered terraces. Bean bags.
Access to the tiered terraces - nook snug seating area.
Terraces have three levels, with an array of seating and relaxation areas.
First Floor:
Drawing room, with huge high sash windows with far reaching sea views. Sofa seating for 8 guests plus additional seating for 6 more. Two fire places (ornamental) at each end of the room.
Kitchen and dining room, fully equipped kitchen, with double oven, microwave oven, induction hob, dishwasher, airfryer, coffee machine (nespresso original) Log burner, double opening fridge and freezer. Dresser full of dinnerware and crockery. A starter pack includes Tea, coffee, fresh milk, butter, local loaf of bread and jam. Oil, salt, pepper, cling film, foil as well as a selection of tea towels, oven gloves and cleaning provisions.
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.
Sleeping and bathing information:
Second Floor
Bed 1 Master bedroom (sleeps 2), view facing with Superking bed. Ensuite shower room and slipper bath with double sink. Smart screen TV
Bed 2 Large King sized bedroom (sleeps 2 ) street side, with large wardrobe, dressing table.
Bed 3 Large king bedroom / street side (sleeps 2) built in wardrobes, chest of drawers.
Bed 4 Side Kingsize bedroom (sleeps 2) hanging space only and chest of drawers.
Bathroom with slipper bath, and walk in enclosure shower.
First Floor
Bed 5 Large kingsize bedroom / street side (sleeps 2) built in wardrobes, chest of drawers. (shower room is on this floor)
Bathroom with walk in shower, wc.
Ground Floor
Bed 6 Accessible King size double bedroom (sleeps 2) view side, Smart screen TV, hanging space, chest of drawers. Ensuite shower room.
Lower Ground Floor
Bed 7 Large kingsize bedroom / view side (sleeps 2) hanging space, chest of drawers. Smart screen TV.
Shower room - with shower, wc.
All larger bedrooms and Master bedrooms can have an option for a day bed in the room (max 2 -sleeps children under 10 only with bedding and towels) supplement of £75 per bed. Must be booked in advance (no later than 7 days before arrival to avoid disappointment)
Services
Wi-Fi throughout
Central heating throughout and underfloor heating
Within 7 bedrooms, 5 bathrooms, 4 reception rooms, tiered terraces and an upper kitchen terrace. Games room area.
Living / Reception areas:
Ground Floor
Entering through into the grand hallway.
Sitting room / TV lounge, seating for 8 / 10 guests, large Smart screen TV, large sash windows.
Morning room, ideal for early risers, a place for watching the sunrise. Coffee machine, cups and items. Smart screen TV. Sofa seating and window seats for 6/8 guests.
Utility room, with washing machine and dryer, with the main bin store area
Shower room and WC (via utility area - great for washing muddy paws via the side access entrance.
Lower ground floor access is via the grand hall way:
Games room / Evening area with Large Smart TV, dart board, fusbol table. Kitchenette with fridge and freezer, coffee machine, microwave, popcorn maker, host of plastic ware for the tiered terraces. Bean bags.
Access to the tiered terraces - nook snug seating area.
Terraces have three levels, with an array of seating and relaxation areas.
First Floor:
Drawing room, with huge high sash windows with far reaching sea views. Sofa seating for 8 guests plus additional seating for 6 more. Two fire places (ornamental) at each end of the room.
Kitchen and dining room, fully equipped kitchen, with double oven, microwave oven, induction hob, dishwasher, airfryer, coffee machine (nespresso original) Log burner, double opening fridge and freezer. Dresser full of dinnerware and crockery. A starter pack includes Tea, coffee, fresh milk, butter, local loaf of bread and jam. Oil, salt, pepper, cling film, foil as well as a selection of tea towels, oven gloves and cleaning provisions.
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.
Sleeping and bathing information:
Second Floor
Bed 1 Master bedroom (sleeps 2), view facing with Superking bed. Ensuite shower room and slipper bath with double sink. Smart screen TV
Bed 2 Large King sized bedroom (sleeps 2 ) street side, with large wardrobe, dressing table.
Bed 3 Large king bedroom / street side (sleeps 2) built in wardrobes, chest of drawers.
Bed 4 Side Kingsize bedroom (sleeps 2) hanging space only and chest of drawers.
Bathroom with slipper bath, and walk in enclosure shower.
First Floor
Bed 5 Large kingsize bedroom / street side (sleeps 2) built in wardrobes, chest of drawers. (shower room is on this floor)
Bathroom with walk in shower, wc.
Ground Floor
Bed 6 Accessible King size double bedroom (sleeps 2) view side, Smart screen TV, hanging space, chest of drawers. Ensuite shower room.
Lower Ground Floor
Bed 7 Large kingsize bedroom / view side (sleeps 2) hanging space, chest of drawers. Smart screen TV.
Shower room - with shower, wc.
All larger bedrooms and Master bedrooms can have an option for a day bed in the room (max 2 -sleeps children under 10 only with bedding and towels) supplement of £75 per bed. Must be booked in advance (no later than 7 days before arrival to avoid disappointment)
Services
Wi-Fi throughout
Central heating throughout and underfloor heating
-
Things You Need to Know
Towels and Linen provided
Wifi
Central heating throughout
Pets allowed, up to 2. Please note that additional pet charges are £35 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.
-
House Rules
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.
The Lead booker must be staying at the property due to contractual terms of booking. Unless agreed otherwise in writing and details of others leading the booking.
Please ensure you check out on time to allow our housekeepers to enter the property and prepare it for the next guests.
Smoking is not permitted in the property at any time.
Please note for insurance purposes the number of guests must not exceed the total occupancy of the house.
For fire safety reasons please do not use any candles in the property.
Please note stag parties are not permitted. Nor are group of under 25’s.
Please note quiet hours are between 11pm and 9am. Please be respectful to our neighbours.
No confetti and no messy decorations are permitted on the walls or frames of the property.
On check out please clear all items including all refrigerated items, dispose of waste in the bins in the utility room area and ensure you turn on the dishwasher before departure. You do not need to strip the beds.
On departure please ensure the heating is set back to 16 degrees, windows closed and all doors are locked and return the keys to the key box.
In the Area
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.
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.
Featured Holiday Cottages
