Holiday Rentals in Winchelsea

12 available vacation rental offers

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Winchelsea holiday rentals
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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.

Delightful 4-bed E. Sussex Cottage - Winchelsea
9.4 20 reviews
Winchelsea
20/10 – 30/10
£277/nighttotal: £2770 (10 )

Delightful 4-bed E. Sussex Cottage

1 3
apartment , Sussex de l'Est
Nelgarde Cottage, a four-bedroom house in Winchelsea, East Sussex, is situated a short 8km drive from Winchelsea Beach, with Rye and Camber Sands also easily accessible.
This self-catering property offers an open-plan kitchen and sitting room with fireplace, three bathrooms, sleeping up to nine guests, and is close to local amenities including a shop, tea room, and pub, plus walking trails.
90 M² Bungalow ∙ 2 Bedrooms ∙ 4 Guests - Winchelsea
Winchelsea
27/06 – 04/07
£115/nighttotal: £805 (7 )

90 M² Bungalow ∙ 2 Bedrooms ∙ 4 Guests

2 2
bungalow
Harbour Barn, a detached house, is located in a tranquil cul-de-sac just moments from Winchelsea Beach, with the beach, a pub, and a café all within 500 meters, and the historic town of Rye a short 5-kilometer drive away.
This 90 square meter bungalow offers accommodation for up to 4 guests across 2 bedrooms, featuring an open-plan living space, a garden conservatory, an enclosed garden with patio seating and BBQ, and on-street parking.
14th-century House In Rye's Historic Citadel - Winchelsea
10 226 reviews
Winchelsea
20/10 – 30/10
£231/nighttotal: £2310 (10 )

14th-century House In Rye's Historic Citadel

3 3
apartment , Sussex de l'Est
Hucksteps, a medieval house in Rye's Citadel, East Sussex, overlooks St Mary's Church and is within easy reach (walking, cycling, or a short drive) of Camber Sands.
This three-bedroom, two-bathroom dwelling sleeps six, boasting a spacious open-plan living area with an inglenook fireplace, a fully equipped modern kitchen, and high-speed Wi-Fi; enjoy nearby Rye's High Street shops and restaurants.
5 East Street Rye, Family And Dog Friendly Cottage In The Heart Of The Old Town - Winchelsea
Winchelsea
20/10 – 30/10
£163/nighttotal: £1630 (10 )

5 East Street Rye, Family And Dog Friendly Cottage In The Heart Of The Old Town

2 3
cottage , Rye
This Rye seaside cottage, situated steps from Rye Castle Museum, Rye Art Gallery, and St Mary's Church, offers immediate beach access and is a 5-minute walk from Rye railway station.
This 7-square-metre self-catering holiday home sleeps four guests in two bedrooms and two bathrooms, boasting a fully equipped kitchen, private patio, garden, barbecue, and spa facilities; free Wi-Fi is included.

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.

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.
River View - Stunning Garden Flat W/ Free Parking - Pass The Keys - Winchelsea
10 1 review
Winchelsea
20/10 – 30/10
£149/nighttotal: £1490 (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.
Rye House - Winchelsea
8.9 25 reviews
Winchelsea
19/08 – 23/08
£303/nighttotal: £1212 (4 )

Rye House

1 5
house , Rye
Rye House, situated in Rye, East Sussex, is approximately 45 kilometres from both Eastbourne and Folkestone, and 106 kilometres from London Gatwick Airport, offering easy access to the historic town centre and its attractions.
This 130-square-metre dwelling boasts three bedrooms, two bathrooms with walk-in showers, a fully equipped kitchen including a dishwasher, and accommodates up to 13 guests, providing ample space for families or groups; free Wi-Fi, a TV and DVD player are also available, with nearby opportunities for cycling and fishing.
93 M² Apartment ∙ 2 Bedrooms ∙ 7 Guests - Winchelsea
8.8 4 reviews
Winchelsea
27/06 – 04/07
£137/nighttotal: £959 (7 )

93 M² Apartment ∙ 2 Bedrooms ∙ 7 Guests

2 2
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.

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.

Rye And Shine - Winchelsea
Winchelsea
19/08 – 23/08
£345/nighttotal: £1380 (4 )

Rye And Shine

3 5
house , Rye
This holiday home in Rye is located 40 kilometres from Eurotunnel UK and Folkestone Central Railway Station, and 27 kilometres from Ashford Eurostar International.
This 70 square meter property offers 3 bedrooms, 1 bathroom, and accommodates up to 10 guests with a fully equipped kitchen, WiFi, and a private entrance, making it ideal for exploring the surrounding area.
The Studio House-design Garden Pass The Keys - Winchelsea
Winchelsea
19/08 – 23/08
£552/nighttotal: £2208 (4 )

The Studio House-design Garden Pass The Keys

1 5
studio , Rye
The Studio House-Design Garden Pass The Keys is located in Rye, 26 kilometres from Ashford Eurostar International, offering convenient access to attractions such as Eurotunnel UK (39 kilometres) and Leeds Castle (42 kilometres).
This spacious 111 square meter studio apartment accommodates up to 10 guests, featuring two bathrooms, a fully equipped kitchen with a dishwasher and oven, complimentary WiFi, and a patio with garden views for outdoor dining.
4 Landgate Cottage Sleeps 4 In Winchelsea Near Rye, East Sussex - Winchelsea
9.6 5 reviews
Winchelsea
20/10 – 30/10
£139/nighttotal: £1390 (10 )

4 Landgate Cottage Sleeps 4 In Winchelsea Near Rye, East Sussex

1 3
cottage , Winchelsea
This smoke-free cottage is situated just a short walk from Winchelsea's Church of St Thomas a Becket and St. Thomas the Martyr, with High Weald and Camber Castle within a 3km radius. The cottage is located in a peaceful rural setting, perfect for those seeking a tranquil getaway. It has received excellent user ratings, making it a popular choice for travellers.
The cottage spans 70 square metres and comfortably accommodates up to four guests in its two bedrooms and two bathrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, a spacious garden, a terrace, and a spa, making it ideal for a relaxing and enjoyable stay.
Extraordinary Huts Ltd - Winchelsea
9.4 550 reviews
Winchelsea
20/10 – 30/10
£307/nighttotal: £3070 (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.

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.

Becky’s Beach Retreat - Winchelsea
9.7 7 reviews
Winchelsea
20/10 – 30/10
£102/nighttotal: £1020 (10 )

Becky’s Beach Retreat

1 3
cabin , Winchelsea Beach
This Winchelsea Beach holiday cottage is located just minutes from the beach, local amenities, and within easy reach of Rye and Hastings, offering a prime spot for exploring historical sites such as Battle.
This two-bedroom property accommodates up to six guests and features a kitchen, internet, a swimming pool, and an on-site bar and restaurant, providing a convenient base for both short breaks and longer stays.
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.
*Location* Spacious Character Flat In Central Rye - Winchelsea
9.6 235 reviews
Winchelsea
20/10 – 30/10
£102/nighttotal: £1020 (10 )

*Location* Spacious Character Flat In Central Rye

1 3
apartment , Sussex de l'Est
This Grade II listed flat in Rye, East Sussex overlooks Rye High Street, Mermaid Street, and The Mint, offering views of the historic town centre.
The one-bedroom apartment sleeps three, features a fully equipped kitchen with oven, fridge, microwave, washing machine and Nespresso machine, and includes a comfortable lounge with a large TV; a travel cot is available (guests must supply bedding).
Caravan 3 A Comfortable And Spacious Caravan - Winchelsea
Winchelsea
20/10 – 30/10
£101/nighttotal: £1010 (10 )

Caravan 3 A Comfortable And Spacious Caravan

2 3
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.
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