Holiday Rentals in Winchelsea

12 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Winchelsea holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Winchelsea

Best Holiday Rentals for Families in Winchelsea

Family holidays in Winchelsea work best when your holiday rental is properly set up with space and city attractions within easy reach.

Winchelsea Sands Holiday Park - Winchelsea
8.1 25 reviews
Winchelsea
20/10 – 30/10
£86/nighttotal: £860 (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.
Stylish Luxury Let In Rye. Walk To Shops/pubs/restaurants + Near Beach - Winchelsea
9.8 48 reviews
Winchelsea
27/06 – 04/07
£212/nighttotal: £1484 (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.
Spacious 4 Bed Family Beach House In Sought After Pett Level Beach, Dogs Welcome - Winchelsea
Winchelsea
27/06 – 04/07
£341/nighttotal: £2387 (7 )

Spacious 4 Bed Family Beach House In Sought After Pett Level Beach, Dogs Welcome

4 2
apartment , HASTINGS
This pet-friendly holiday home in Hastings is located a 6-minute walk from Pett Level Road Beach and a 5-minute drive from Hastings Country Park, offering convenient access to seaside activities and coastal walks.
This 4-bedroom, 2-bathroom holiday home accommodates up to 8 guests, featuring a fully equipped kitchen with a microwave and dishwasher, complimentary Wi-Fi, on-site laundry facilities, and a garden, with parking available.
Rye House - Winchelsea
9.9 50 reviews
Winchelsea
19/08 – 23/08
£279/nighttotal: £1116 (4 )

Rye House

3 5
cottage , Rye
Rye House is located in the charming historic town of Rye, just 43km from Leeds Castle and 45km from both Eastbourne Miniature Steam Railway Adventure Park and Eastbourne Pier. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The house offers 3 bedrooms and 2 bathrooms across 130 square metres of space. Guests can enjoy a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as free Wi-Fi, parking, and a TV with a DVD player.

Top Holiday Rentals with Parking in Winchelsea

Driving to Winchelsea? Your holiday rental includes a car park, making the city centre simple to navigate from arrival.

Caravan 3 A Comfortable And Spacious Caravan - Winchelsea
Winchelsea
27/06 – 04/07
£104/nighttotal: £728 (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.
Rother - Studio In Rye - Location,location,location !!! - Winchelsea
9.6 224 reviews
Winchelsea
20/10 – 30/10
£159/nighttotal: £1590 (10 )

Rother - Studio In Rye - Location,location,location !!!

1 3
studio , Rye
This Rye studio apartment is centrally located, within walking distance of Rye Castle Museum and Rye's historic town centre, approximately 40-48km from Eurotunnel and Leeds Castle.
The 50 square metre self-catering unit offers a spacious layout, sleeping one person, with a fully equipped kitchen (fridge, microwave), private entrance, parking, and pet-friendly accommodation (extra charge).
Eastwoods Cottage - Winchelsea - Winchelsea
Winchelsea
20/10 – 30/10
£129/nighttotal: £1290 (10 )

Eastwoods Cottage - Winchelsea

2 3
apartment , East Sussex
This two-bedroom holiday cottage in Winchelsea, East Sussex, is situated a 5-minute walk from High Weald National Park and a 6-minute walk from St. Thomas the Martyr Church.
This family-friendly apartment accommodates four guests and offers free Wi-Fi, on-site parking, and a well-equipped kitchen, with a washing machine provided for guest convenience.
River House - Winchelsea
9.4 24 reviews
Winchelsea
20/10 – 30/10
£162/nighttotal: £1620 (10 )

River House

3 3
house , Playden
River House, a three-bedroom property in Playden, East Sussex, offers peaceful accommodation approximately 40km from the Eurotunnel and 45km from Folkestone Central railway station.
This self-catering house sleeps up to 11 guests, boasting a fully equipped kitchen, terrace, free Wi-Fi, and free private parking; pets are welcome.

Frequently asked questions about holiday rentals in Winchelsea

  • Which walking or cycling routes are the best in Winchelsea?

    The coastal path is a great walk, offering stunning views of the English Channel. There are also plenty of shorter walks around Winchelsea itself, taking you past the historic walls and the old church. For cycling, try the route along the Romney Marsh, a flat and easy ride with beautiful scenery.
  • What are the best Airbnb and holiday rentals in Winchelsea?

  • What sports or outdoor activites can visitors enjoy in and around Winchelsea?

    Winchelsea is a great place for walking and cycling, and you can also enjoy sailing and kayaking on the nearby coast. If you're looking for something more active, there are several golf courses in the area, and you can also go horse riding on the Romney Marsh. There's also a lovely beach at Camber Sands, about 6 miles away.
  • What are the most popular Airbnbs 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 miles away. You can also easily reach Brighton and Canterbury by car, and London is about an hour and a half away by train.
  • What are the best holiday rentals with a pool in Winchelsea?

    Rye Harbour Caravan, Beautiful 3 Bedroom Holiday Home Sleeps 8 People and Henry-oscar House are the best holiday rentals with a pool in Winchelsea.

  • What amenities are commonly available in vacation rentals in Winchelsea?

    You'll find that most vacation rentals in Winchelsea have basic amenities like a kitchen, bathroom, and bedrooms. Many rentals also offer Wi-Fi, a washing machine, and a TV. Some even have gardens or patios. It's best to check the listing for specifics.
  • What are the best rentals for families and kids in Winchelsea?

    The best rentals for families and kids in Winchelsea are Wheelwrights, Beautiful Flat On Rye High Street - & Marsh View and Rye Bay Beach Apartment.

  • What time of year is best to rent a vacation rental Winchelsea?

    Winchelsea is lovely all year round, but the best time to visit is in the spring or autumn when the weather is mild and the crowds are smaller. Summer is also a popular time to visit, but it can get quite busy.
  • What are the best rentals or Airbnbs with a jacuzzi in Winchelsea?

    The best holiday rentals or Airbnb with a jacuzzi in Winchelsea are Stowaway Beach House Camber Sands, Kinara In Camber and Henry-oscar House.

  • What are the local dishes in Winchelsea region?

    The local cuisine in the area is known for its fresh seafood, so be sure to try the local fish and chips. You can also enjoy traditional pub grub, and the area is known for its lamb. There are a few excellent restaurants in Winchelsea and Rye.

Destinations nearby

Check Out Holiday Rentals with a Balcony in Winchelsea

A terrace with city skyline views is a fantastic reason to book a holiday rental in Winchelsea. View our top picks and start comparing now.

Scallop Cottage Oasis Of Calm - Pass The Keys - Winchelsea
9.6 7 reviews
Winchelsea
20/10 – 30/10
£166/nighttotal: £1660 (10 )

Scallop Cottage Oasis Of Calm - Pass The Keys

2 3
house , Rye
Scallop Cottage, a two-bedroom house in Rye, East Sussex, is situated approximately 45-48 kilometres from Leeds Castle, Eastbourne, and Folkestone.
This 74 square metre property sleeps five, boasting a fully equipped kitchen with dishwasher and microwave, a private garden, and free Wi-Fi; a washing machine is also available.
Tilling View With Private Parking - Winchelsea
9.1 56 reviews
Winchelsea
20/10 – 30/10
£143/nighttotal: £1430 (10 )

Tilling View With Private Parking

2 3
house , Rye
This house in Rye, East Sussex is located just 1.4 kilometres from Camber Castle, offering river views and a patio.
The 79 square metre property features two bedrooms, two bathrooms, a private garden, and a fully equipped kitchen with a dishwasher.
Beautiful Sussex Coastal Holiday Home - Winchelsea
Winchelsea
19/08 – 23/08
£355/nighttotal: £1420 (4 )

Beautiful Sussex Coastal Holiday Home

4 5
house , Winchelsea
This recently renovated holiday cottage is located in Winchelsea, 32 kilometres from Ashford Eurostar International and 84 kilometres from London Gatwick Airport.
This 25 square metre holiday cottage sleeps 11 guests and features a garden, terrace, fully equipped kitchen with a dishwasher, and complimentary Wi-Fi.
Matchbox - Winchelsea
9.2 60 reviews
Winchelsea
27/06 – 04/07
£170/nighttotal: £1190 (7 )

Matchbox

2 2
house , Winchelsea
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.

Find the Best Dog-Friendly Self-Catering Rentals in Winchelsea

Your dog is as welcome as you are. These pet-friendly holiday rental and Airbnbs in Winchelsea provide easy access to local dog parks and city walks. See what's available.

Cottage ∙ 3 Bedrooms ∙ 6 Guests - Winchelsea
10 3 reviews
Winchelsea
19/08 – 23/08
£446/nighttotal: £1784 (4 )

Cottage ∙ 3 Bedrooms ∙ 6 Guests

3 5
cottage
This holiday cottage in Playden is situated on the rural outskirts of Rye, East Sussex, offering a 10-minute walk to the medieval town and a short drive to Camber Sands.
Sleeping up to six guests in three bedrooms, this family-friendly property features a spacious, enclosed garden, a log burner, a separate family room with a sofa bed, Wi-Fi, and private parking for three cars.
93 M² Apartment ∙ 2 Bedrooms ∙ 7 Guests - Winchelsea
8.8 4 reviews
Winchelsea
19/08 – 23/08
£286/nighttotal: £1144 (4 )

93 M² Apartment ∙ 2 Bedrooms ∙ 7 Guests

2 5
apartment
This ground-floor flat is centrally located in Rye's medieval town centre, a short walk from Rye's historic landmarks, shops, and cafes.
The 93 square metre (0.093 hectare) apartment offers two bedrooms, two bathrooms, a garden, parking, and sleeps up to seven guests, boasting a fully equipped kitchen including a fridge, microwave, and dishwasher.
Delightful 2 Bedroom Hideaway Close To Beach - Winchelsea
9.9 119 reviews
Winchelsea
20/10 – 30/10
£122/nighttotal: £1220 (10 )

Delightful 2 Bedroom Hideaway Close To Beach

2 3
apartment , Winchelsea Beach
This charming cottage is located on a quiet street in Winchelsea Beach Village, just a 5-minute walk from the beach and 2 minutes from the Co-op supermarket. Guests have consistently rated the accommodation as excellent for its cleanliness, location, and overall experience.
The cottage has two bedrooms and one bathroom, comfortably sleeping up to four guests. It features a well-equipped kitchen, a private garden with a sun-drenched courtyard, free parking, and easy access to local amenities, making it the perfect base for exploring the beautiful Sussex coast.
Stoats Old River Way - Winchelsea
9.7 37 reviews
Winchelsea
27/06 – 04/07
£266/nighttotal: £1862 (7 )

Stoats Old River Way

1 2
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.
©2026 cozycozy.com