Matchbox is a holiday home in Winchelsea, just 42 kilometres from Eastbourne Miniature Steam Railway Adventure Park and 43 kilometres from Eastbourne Pier, offering a tranquil escape in a charming historic town. Guests have consistently rated the property excellent for its location, cleanliness and overall experience. This two-bedroom property spans 89 square metres and comfortably sleeps four guests. Enjoy modern amenities including a fully equipped kitchen, private terrace, washing machine, free Wi-Fi, and a flat-screen TV, making it ideal for a relaxing and comfortable stay.
Winchelsea
27/06 – 04/07
A$226/nighttotal: A$1582 (7 )
2 Bed In Rye Oc-rh1045
2 2
house , Rye
This 2-bedroom holiday home in Rye is located 27 kilometres from Ashford Eurostar International, with Eurotunnel UK and Folkestone Central Railway Station 40 kilometres away, and Leeds Castle and Folkestone Harbour within a 45-kilometre radius. This property offers WiFi, a microwave oven, a dishwasher, a washing machine, and a fireplace, accommodating up to 7 guests with a garden for outdoor relaxation.
9.6 62 reviews
Winchelsea
27/06 – 04/07
A$218/nighttotal: A$1526 (7 )
Applecote A Studio Apartment For Two Rye, East Sussex
1 2
studio , Rye
Applecote is a studio apartment located in Rye, East Sussex, just 42km from Eurotunnel UK and 43km from Leeds Castle, making it a great base for exploring the area's historic charm and picturesque countryside. This accommodation has received excellent ratings for its location, cleanliness, and overall user experience. The studio features a well-equipped kitchen, a private terrace with garden views, and a cosy fireplace. Guests can enjoy the convenience of on-site parking, air conditioning, and access to a spa, as well as the opportunity to explore the nearby hiking trails.
Winchelsea
27/06 – 04/07
A$198/nighttotal: A$1386 (7 )
Caravan 3 A Comfortable And Spacious Caravan
1 2
chalet , Winchelsea
This Winchelsea chalet is located 83.7 kilometres from London Gatwick Airport and offers a private terrace, complimentary private parking, and free WiFi. This comfortable accommodation sleeps up to seven guests in one bedroom and one bathroom, featuring a fully equipped kitchen, a flat-screen TV, and a strictly non-smoking environment.
9.5 39 reviews
Winchelsea
20/10 – 30/10
A$266/nighttotal: A$2660 (10 )
4 Landgate Cottages
2 3
house , Winchelsea
4 Landgate Cottages, Winchelsea, offers a self-catering property 42km from the Eastbourne Miniature Steam Railway Adventure Park and 43km from Eastbourne Pier, conveniently located near Winchelsea's historic town centre. This two-bedroom house, boasting 70 square metres of floor space, includes a fully equipped kitchen with dishwasher, private garden, free parking, and Wi-Fi; sleeping up to four guests comfortably.
10 42 reviews
Winchelsea
20/10 – 30/10
A$298/nighttotal: A$2980 (10 )
Pretty 18th Century Cottage Centrally Situated On Mermaid Street In Rye
2 3
cottage , Rye
Mermaid Cottage, a two-bedroom holiday home, is situated at the top of Mermaid Street in Rye's historic citadel, a 0.8 km walk from Rye Station and close to Rye's attractions including the 1066 Country Walk. This self-catering property sleeps four, boasting a living room, dining room, kitchen with fridge and microwave, a bathroom with shower bath, a secluded courtyard garden, and a jacuzzi, plus free Wi-Fi.
Winchelsea
19/08 – 23/08
A$410/nighttotal: A$1640 (4 )
Luxford - Elms Farm Cottages
1 5
apartment , Sussex de l'Est
Elms Farm Cottages - Luxford is a self-catering cottage located in the historic Cinque Port town of Winchelsea, East Sussex, offering free WiFi and private parking. This spacious holiday home accommodates up to six guests across four bedrooms and two bathrooms, featuring a fully equipped kitchen, dining area, and a patio with garden views, ideal for exploring the nearby coastline and countryside.
Winchelsea
27/06 – 04/07
A$234/nighttotal: A$1638 (7 )
Pass The Keys | Bosun's Loft - Superb Views!
1 2
apartment , Rye
This Rye apartment, near Rye's beach, is within walking distance of Lamb House and Landgate, offering easy access to Rye's historical landmarks. The 56 square metre flat features one bedroom, one bathroom, and sleeps two, with a kitchen including a fridge and microwave; secure booking via Truvi is available.
9.5 30 reviews
Winchelsea
19/08 – 23/08
A$1012/nighttotal: A$4048 (4 )
Designer Central Rye Home With Two Gardens
1 5
apartment , Sussex de l'Est
This three-bedroom Rye apartment enjoys a central location in East Sussex, a two-minute walk from Rye train and bus stations, offering easy access to Camber Sands beach (approx. 16km), Hastings (approx. 24km), and other East Sussex attractions. The self-catering flat features two private gardens, sleeps six guests, includes a fridge and dishwasher, and boasts stylish interiors with high ceilings, providing a spacious and comfortable stay.
10 34 reviews
Winchelsea
19/08 – 23/08
A$1123/nighttotal: A$4492 (4 )
The Cottage In Mermaid Passage, Rye, East Sussex
1 5
apartment , Sussex de l'Est
This Rye cottage, situated in the historic Mermaid Passage, is moments from the Mermaid Inn and within easy driving distance of Pett Level and Winchelsea beaches. Sleeping six guests, this three-bedroom property boasts a fully equipped kitchen with Smeg appliances, multiple living spaces including a wood burner and Smart TV, and a private garden; nearby attractions include Tillingham winery.
9.2 42 reviews
Winchelsea
27/06 – 04/07
A$256/nighttotal: A$1792 (7 )
Honey Cottage
2 2
house , Rye
Honey Cottage, a recently renovated holiday home in Rye, East Sussex, is situated 42km from the Eurotunnel and 43km from Leeds Castle. This 70 square metre property sleeps four guests in two bedrooms and one bathroom, offering a fully equipped kitchen, private terrace, garden, spa, and free Wi-Fi.
Winchelsea
27/06 – 04/07
A$253/nighttotal: A$1771 (7 )
Pass The Keys | The Lookout At Rye - Great Views
1 2
apartment , Rye
This Rye apartment, centrally located near Rye railway/bus station and within walking distance of Rye Harbour Nature Reserve, offers stunning views of rooftops and countryside. The 56 square metre flat features a one-bedroom layout with a separate study, a designer bathroom, Nespresso machine, and is close to Rye's shops, restaurants (such as The Hoof), Camber Sands beach (10-minute drive), and Rye marina.
Best family friendly Winchelsea holiday rentals
Among the 4 accommodations in Winchelsea, here are the 4 best family friendly rentals
8.6 55 reviews
Winchelsea
27/06 – 04/07
A$313/nighttotal: A$2191 (7 )
Rose Mullion Cottage
3 2
house , Pett
Rose Mullion Cottage is located in Pett, a charming village, just 39 kilometres from Eastbourne Miniature Steam Railway Adventure Park and Eastbourne Pier. This property has received excellent ratings for location, cleanliness and user experience. The cottage offers three bedrooms and a comfortable living space, perfect for families or groups of friends. The modern kitchen is fully equipped with a dishwasher and oven, and there's a private terrace, a garden, a spa, and free Wi-Fi for your enjoyment.
9.7 37 reviews
Winchelsea
20/10 – 30/10
A$399/nighttotal: A$3990 (10 )
Stoats Old River Way
1 3
house , Winchelsea
This spacious four-bedroom house, situated on Stoats Old River Way in Winchelsea, offers easy access to attractions such as the Eastbourne Miniature Steam Railway Adventure Park (43km), Eastbourne Pier (45km), and the Eurotunnel UK (45km). The self-catering property features a fully equipped kitchen, private patio with barbecue, free Wi-Fi, parking, a spa, and outdoor play equipment, comfortably accommodating a family and providing a relaxing getaway near hiking trails.
8.9 28 reviews
Winchelsea
20/10 – 30/10
A$263/nighttotal: A$2630 (10 )
Southbank
3 3
house , Rye
This Rye holiday home, Southbank, is situated approximately 40 kilometres from Eurotunnel UK, 43 kilometres from Leeds Castle, and 45 kilometres from Folkestone Central railway station. The three-bedroom property offers free private parking, a fully equipped kitchen with dishwasher, a private terrace and garden, plus Wi-Fi; ideal for families or groups of up to six, enjoying a self-catering stay with access to a spa.
9.6 145 reviews
Winchelsea
20/10 – 30/10
A$250/nighttotal: A$2500 (10 )
Rosendal – Cosy Cottage For Countryside & Coast
3 3
apartment , Sussex de l'Est
Rosendal Cottage, a three-bedroom house, is situated on the edge of Winchelsea, East Sussex, a short walk (less than 0.8 km) from the town centre and close to the High Weald Area of Outstanding Natural Beauty, offering easy access to Rye and the coast. This family-friendly dwelling boasts an open-plan kitchen/dining area, a cosy lounge with a wood burner and Freesat TV, plus a garden, parking, and sleeps six, with amenities including a dishwasher and WiFi; nearby attractions include Winchelsea beach, the 1066 trail and Rye Harbour Nature Reserve.
Best Winchelsea holiday rentals with parking
10 1 review
Winchelsea
20/10 – 30/10
A$284/nighttotal: A$2840 (10 )
River View - Stunning Garden Flat W/ Free Parking - Pass The Keys
2 3
apartment , Rye
This Rye ground-floor flat is centrally located in the medieval town, within easy walking distance of Rye Castle Museum and the Jerwood Gallery. The 93-square-metre self-catering apartment offers two bedrooms, two bathrooms, a private garden, parking, and sleeps up to seven guests, boasting modern amenities including a dishwasher and Wi-Fi.
8.6 5 reviews
Winchelsea
27/06 – 04/07
A$247/nighttotal: A$1729 (7 )
Summer Breeze Caravan On Winchelsea Sands Holiday Park
2 2
house , Winchelsea
This caravan is situated within Winchelsea Sands Holiday Park in Winchelsea, 33 kilometres from Ashford International, offering a peaceful setting with proximity to outdoor activities like hiking and cycling. The accommodation provides 2 bedrooms, 2 bathrooms, a kitchen with a fridge and microwave, a terrace with garden views, a swimming pool, on-site restaurant and bar, free WiFi, and free private parking, accommodating up to 11 guests.
9.8 48 reviews
Winchelsea
27/06 – 04/07
A$403/nighttotal: A$2821 (7 )
Stylish Luxury Let In Rye. Walk To Shops/pubs/restaurants + Near Beach
3 2
apartment , Rye
Bee Cottage is a stylish house located a short ten-minute walk from Rye town centre, offering easy access to shops, restaurants, and historic attractions. It has received excellent ratings for location, cleanliness, and overall user experience. This three-bedroom home comfortably sleeps six guests and spans 80 square metres. Amenities include a well-equipped kitchen, a private garden with a patio and barbecue, and entertainment options like an Xbox, DVD player, and a record player.
9.1 58 reviews
Winchelsea
20/10 – 30/10
A$308/nighttotal: A$3080 (10 )
Spring Crescent Cottage In Rye
2 3
house , Rye
Spring Crescent Cottage, a two-bedroom house in Rye, East Sussex, is situated 29km from Ashford International and offers easy access to Folkestone (48km) and other Kent and East Sussex attractions. This pet-friendly property sleeps seven, features free Wi-Fi, and is ideal for families or couples seeking a peaceful base for exploring Rye's historic town centre and the surrounding coastline.
Frequently asked questions about holiday rentals in Winchelsea
What are some interesting places to visit in or near Winchelsea?
Winchelsea itself is a charming medieval town with the ruins of the old town walls, a historic church, and quaint cobbled streets. You can also visit Rye, a nearby historic town with a castle and a bustling market. For stunning coastal views, head to the nearby Camber Sands beach.
What are the best Airbnb and holiday rentals in Winchelsea?
Which walking or cycling routes are the best in Winchelsea?
The South Coast Path runs along the cliffs near Winchelsea, offering breathtaking views. For a shorter walk, try the circular route around the old town walls. If you're into cycling, there's a lovely route along the River Rother to Rye.
What sports or outdoor activites can visitors enjoy in and around Winchelsea?
Winchelsea is great for walking, cycling, and birdwatching. You can also enjoy watersports at Camber Sands, including kite surfing and windsurfing. For something more adventurous, try a round of golf at the nearby Rye Golf Club.
What are the best holiday rentals with a pool in Winchelsea?
What other towns or cities can be easily accessed from Winchelsea?
Rye is just a short drive away, and Hastings is about 15 minutes by car. You can also easily reach the historic city of Canterbury by car or train. The towns of Bexhill-on-Sea and Eastbourne are also within easy reach.
What are the best rentals for families and kids in Winchelsea?
What amenities are commonly available in vacation rentals in Winchelsea?
Most vacation rentals in Winchelsea offer basic amenities like a kitchen, bathroom, and comfortable beds. Many also have a garden or patio, and some even have sea views. You can find rentals with Wi-Fi, washing machines, and even hot tubs.
What are the best rentals or Airbnbs with a jacuzzi in Winchelsea?
What time of year is best to rent a vacation rental Winchelsea?
The best time to visit Winchelsea is during the spring or autumn when the weather is mild and the crowds are smaller. The summer months are popular for beach holidays, but it can get quite busy. Winter can be chilly, but it's a great time to enjoy the town's quieter side.
Destinations nearby
Best Winchelsea holiday rentals with a balcony
8.9 20 reviews
Winchelsea
20/10 – 30/10
A$183/nighttotal: A$1830 (10 )
White Haven - With 2 Double Rooms
3 3
apartment , Winchelsea Beach
White Haven is a 3-bedroom holiday home situated within the Winchelsea Sands holiday park, a short walk from the stunning Winchelsea Beach. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience. This spacious holiday home, spanning 39 square metres, comfortably accommodates up to 7 guests. Amenities include a fully equipped kitchen, a private terrace, and access to a swimming pool, tennis court, and parking.
Winchelsea
19/08 – 23/08
A$1051/nighttotal: A$4204 (4 )
The Studio House-design & Garden | Pass The Keys
3 5
studio , Rye
This studio apartment is situated in the historic centre of Rye, just 2 minutes on foot from the train and bus stations, placing you within immediate reach of local shops, galleries, and restaurants. Offering 111 square meters of space for up to 6 guests, this property features two bathrooms, a kitchen with a fridge and dishwasher, and two private outdoor areas, providing an ideal base for exploring Rye Castle Museum and the 1.6 kilometer walk to Camber Sands beach.
9.4 550 reviews
Winchelsea
20/10 – 30/10
A$585/nighttotal: A$5850 (10 )
Extraordinary Huts Ltd
2 3
farm , Rye
Extraordinary Huts is a farm stay in Rye, East Sussex, just a short drive from Camber Castle and the beautiful East Sussex countryside. The farm stay consistently receives excellent user ratings for its cleanliness, location, and overall experience. Each self-catering unit comes with a kitchen, dining area, and living room, giving guests the flexibility to relax and enjoy their own space. Guests can enjoy the outdoor space, including a terrace, garden, and barbecue, and there are also opportunities for hiking and windsurfing nearby.
9.8 68 reviews
Winchelsea
19/08 – 23/08
A$652/nighttotal: A$2608 (4 )
Oak House
1 5
house , Rye
Oak House, a three-bedroom property in Rye, East Sussex, is conveniently located approximately 42 kilometres from the Eurotunnel UK and 43 kilometres from Leeds Castle. This family-friendly house, sleeping up to six, boasts a private terrace, garden, spa, and fully equipped kitchen including a dishwasher; free Wi-Fi is also available.
Best pet friendly Winchelsea holiday rentals
Among the 4 accommodations in Winchelsea, here are the 4 best pet friendly rentals
8.1 25 reviews
Winchelsea
20/10 – 30/10
A$164/nighttotal: A$1640 (10 )
Winchelsea Sands Holiday Park
3 3
apartment , Winchelsea
Winchelsea Sands Holiday Park apartments offer self-catering accommodation in Winchelsea, East Sussex, conveniently located near Winchelsea's historic town centre and approximately 43-50km from Eastbourne and the Eurotunnel terminal. These pet-friendly flats, each with a private terrace, 20 square metre floor area, and sleeping up to 11 guests, include free Wi-Fi, parking, fully equipped kitchens, and private bathrooms; ideal for exploring the nearby coast.
10 204 reviews
Winchelsea
20/10 – 30/10
A$221/nighttotal: A$2210 (10 )
Daisy Tatham Cottage, Rye
1 3
apartment , Sussex de l'Est
Daisy Tatham Cottage, a Victorian terraced house in Rye, East Sussex, is located within walking distance of Rye train station and the historic Cinque Ports town centre. This dog-friendly holiday home sleeps five guests across three floors, offering two bedrooms, a futon in a third bedroom/lounge, a private courtyard garden, and amenities including a washing machine, BBQ, and log burning stove.
10 2 reviews
Winchelsea
19/08 – 23/08
A$2498/nighttotal: A$9992 (4 )
Chequer - A Holiday Let That Sleeps 14 Guests In 7 Bedrooms
7 5
apartment , Rye
This seven-bedroom Rye holiday home, a five-minute walk from Rye Castle Museum and Rye train station, offers easy access to the 1066 Country Walk. The 511-square-metre property boasts six bathrooms, a fully equipped kitchen including dishwasher and microwave, plus Wi-Fi, making it ideal for large groups; nearby attractions include Lamb House and Rye Farm World.
10 1 review
Winchelsea
20/10 – 30/10
A$195/nighttotal: A$1950 (10 )
Caravan 7, A Modern Unit With Gch + Dg
1 3
cabin , Winchelsea Beach
This Winchelsea Beach holiday lodge offers a tranquil retreat within a small caravan park, located just a short 200-meter walk from Winchelsea Beach and its adjacent Nature Reserve, with convenient public transport links to Rye and Hastings. This modern, two-bedroom accommodation for four guests includes a well-equipped open-plan kitchen and living area with a smart TV, gas central heating, double glazing, and a private outdoor seating area, making it suitable for year-round stays.