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Winchelsea vacation rentals

We found 759 vacation rentals — enter your dates for availability

Discover a selection of 5 homes and other vacation rentals in Winchelsea that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation rentals have the amenities you expect for your stay, which might include hot tub and a washer and dryer. No matter what you're looking for, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Winchelsea

Showing deals for:Nov 14 - Nov 21

Image gallery for Countryside House Near Battle

Pool
10 out of 10 rating
Exceptional
(13 reviews)

Countryside House Near Battle

Battle, England

10% off
Price is CA $957
CA $7,541 total
includes taxes & fees
Countryside House Near Battle

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Find out more about Winchelsea

Find out more about Winchelsea

Why visit Winchelsea

  1. Charming Beaches: Enjoy the picturesque beaches of Winchelsea, perfect for relaxation and family outings.
  2. Rich History: Explore historic churches and landmarks that reflect the town's fascinating past.
  3. Outdoor Adventures: Discover nature reserves and scenic landscapes ideal for hiking and exploring.
  4. Budget-Friendly Accommodations: Choose from a variety of vacation rentals that cater to all budgets.
  5. Welcoming Atmosphere: Experience the friendly community vibe that makes Winchelsea a delightful getaway.

Popular types of accommodation in Winchelsea

Are you planning a getaway to Winchelsea? Discover the perfect place to stay with our selection of vacation rentals that cater to every need. From charming cottages and houses to comfortable apartments, Winchelsea offers a variety of options for your ideal holiday. Whether you're seeking a cozy retreat or a beachside escape, our Winchelsea vacation rentals promise transparency, savings, and peace of mind for your stay.

  • Cottages: The top choice for visitors in Winchelsea, these charming dwellings offer a cozy and picturesque stay.
  • Houses: A great option for families or groups, these homes provide ample space and comfort.
  • Apartments: Perfect for those seeking convenience, apartments offer modern amenities in a central location.
  • Caravan Parks: For a unique experience, caravan parks allow you to enjoy the outdoors while having your own space.
  • Cabins: A lovely retreat for nature enthusiasts, cabins provide a rustic experience amidst beautiful scenery.**

Top attractions in Winchelsea

Winchelsea offers a delightful mix of beach, outdoor, and scenic experiences perfect for a vacation. With its charming beaches, nature reserves, and historic churches, visitors can enjoy a variety of activities catering to culture, family fun, and outdoor adventures. Whether you're exploring the local sights or simply soaking in the beautiful surroundings, Winchelsea is an ideal destination for a memorable getaway.

  1. Camber Sands: A stunning beach located 6.4km from Winchelsea, Camber Sands offers a delightful seaside experience with its expansive sandy shores, perfect for sunbathing and beach activities.
  2. Rye Harbour Nature Reserve: Situated 3.2km away, this reserve is a haven for wildlife enthusiasts. Enjoy the tranquil scenery, friendly locals, and a rich historical backdrop while exploring its diverse habitats.
  3. Great Dixter House and Gardens: Located 11.3km from Winchelsea, this historic house showcases exquisite gardens and rich cultural heritage, providing a glimpse into English gardening traditions.

Things to do recommended for couples

For a romantic getaway in Winchelsea, visit the Chapel Down Winery for a delightful wine tasting, enjoy a show at the White Rock Theatre, or take a scenic ride on the East Hill Lift for breathtaking views. Each experience offers a unique charm perfect for couples.

Things to do recommended for families

During your family vacation in Winchelsea, enjoy thrilling adventures at BattleZone Live and Clambers, both featuring family-friendly arcade fun just 12.9km away. For a relaxing day, visit Bewl Water, located 112.9km away, offering wellness and beautiful scenery for the whole family.

Things to do recommended for groups

Embark on the scenic 1066 Country Walk for outdoor adventure, catch a captivating show at the Stables Theatre for a dose of culture, or enjoy a round of golf at Sedlescombe Golf Club for some friendly competition, all within a short drive from Winchelsea.

What do I need to keep in mind when booking a vacation in Winchelsea

If you're planning a trip with a group, family, or pets, or if you're seeking extended stays, it's important to prioritise your preferences when filtering your options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Winchelsea with a group: Think about how many bedrooms you'll require, along with additional features like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Winchelsea with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with having access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Winchelsea: For many, a family getaway isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Winchelsea: If you’re seeking vacation rentals with great offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Winchelsea

Winchelsea, nestled in East Sussex, offers a charming blend of beachside relaxation and rich history. Explore its friendly atmosphere while enjoying scenic views and outdoor activities. Ideal for budget and luxury travellers alike, you’ll find affordable vacation rentals and delightful local spots. Nearby attractions enhance your experience with a taste of historical charm and stunning landscapes. Welcome to Winchelsea, where a relaxing getaway awaits!

  • Rye: Located a mere 3.2km from Winchelsea, Rye is a charming coastal city known for its historic streets and stunning scenery. Visitors are drawn to its picturesque architecture, including medieval buildings and cobbled pathways. The city offers a range of outdoor activities, from exploring the scenic beach to enjoying a round of golf at nearby courses. Highlights include family-friendly beaches and the natural beauty of the surrounding dunes, making it an ideal spot for a day of relaxation or adventure.
  • Hastings: Situated 12.9km from Winchelsea, Hastings is a vibrant seaside town packed with family-friendly attractions. Known for its rich history and beautiful coastline, visitors can explore the beach and indulge in outdoor activities like hiking and enjoying the local theatre scene. The funicular offers unique views of the town, and the sandy beaches are perfect for family outings. Hastings invites you to discover its charming streets, delectable dining options, and historical landmarks.
  • Icklesham: Nestled in the vicinity of Winchelsea, Icklesham is a quaint village that offers a peaceful retreat for nature lovers. With its stunning beaches and beautiful scenery, this village is perfect for outdoor enthusiasts. Visitors can enjoy recreational areas, golf courses, and the tranquil atmosphere of family beaches nearby. The picturesque dunes and coastal views provide an inviting backdrop for a leisurely stroll or a day spent unwinding in the beauty of the English countryside.

Best time to go to Winchelsea

If you're planning a trip to Winchelsea, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in April and July to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January41.4°F (5.2°C)Light RainMostly CloudyAverageAverage
February41.9°F (5.5°C)Light RainMostly CloudyAverageSlightly Low
March44.6°F (7.0°C)No Rain (Dry)Mostly CloudyAverageAverage
April48.2°F (9.0°C)No Rain (Dry)Mostly SunnyModerately HighAverage
May53.4°F (11.9°C)Light RainMostly SunnyAverageAverage
June59.2°F (15.1°C)Light RainMostly SunnyAverageAverage
July63.0°F (17.2°C)Light RainMostly SunnyModerately HighSlightly High
August63.3°F (17.4°C)Light RainMostly SunnyModerately HighSlightly High
September59.7°F (15.4°C)Light RainMostly SunnyAverageSlightly Low
October55.0°F (12.8°C)Light RainMostly CloudyModerately LowAverage
November48.4°F (9.1°C)Light RainMostly CloudyModerately LowSlightly Low
December44.1°F (6.7°C)Light RainMostly CloudyModerately LowSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? It might be beneficial to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to considerable savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to narrow down your options by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly area where you can easily plan new trips, resume your previous ones, or manage your travel arrangements. You can view the properties you’ve saved or booked, which are conveniently organized into Potential, Upcoming, or Current Trips. To get started with Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Travel to friendly Winchelsea

The area's churches and monuments are just a few of the reasons to vacation in Winchelsea. This welcoming and relaxing city entices travelers with its restaurants and gardens. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in Winchelsea

Are you looking for attractions to see while you're in town? Venture out of your vacation home and experience everything that makes Winchelsea a fun spot to vacation. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • East Hill Lift (6.9 mi / 11.1 km)
  • The Chapel Down Winery (8 mi / 12.9 km)
  • Gusbourne Estate Winery (9.4 mi / 15.1 km)
  • Rye Golf Club (2.9 mi / 4.6 km)
  • Carr Taylor Vineyard (6.3 mi / 10.2 km)
  • Blue Reef Aquarium (6.9 mi / 11 km)

Exploring the natural features in Winchelsea

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Winchelsea. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Winchelsea Beach (1.2 mi / 2 km)
  • Pett Level Beach (2 mi / 3.2 km)
  • 1066 Country Walk (2.2 mi / 3.6 km)
  • Rye Harbour Nature Reserve (2.5 mi / 4 km)
  • Camber Sands (3.8 mi / 6.1 km)
  • Hastings Country Park (5 mi / 8 km)

How to get to and around Winchelsea

Fly into Gatwick Airport (LGW), the closest airport, located 41.2 mi (66.3 km) from the city center.

Frequently asked questions

What is the best area to stay in Winchelsea when booking a vacation rental?
When considering a vacation rental in Winchelsea, the area around the historic town centre is an excellent choice. This charming neighbourhood is steeped in history, with its cobbled streets and medieval architecture, making it a delightful place to explore on foot. Here, you can easily access top attractions such as the 13th-century St. Thomas' Church, known for its impressive medieval tower, and the nearby Winchelsea Beach, which offers a lovely spot for a leisurely stroll or a picnic.

In addition to the town centre, the area surrounding the quaint Winchelsea Station is also appealing for visitors. This location provides a more tranquil setting while still being close to local amenities and scenic views of the surrounding countryside. The station area serves as a great starting point for walks along the picturesque landscapes that characterise this part of East Sussex.
How much does it cost to rent a vacation home in Winchelsea?
Prices for vacation rentals in Winchelsea vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winchelsea to more spacious homes.
Are there any discounts for Winchelsea vacation house rentals?
You can find great discounts on house rentals in Winchelsea on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Winchelsea?
For renting a beach house in Winchelsea, the area near the picturesque Winchelsea Beach is an excellent choice. This charming coastal village offers a selection of seaside properties, many of which feature stunning views of the English Channel and easy access to the beach. Travellers can expect amenities such as private gardens, outdoor seating areas, and fully equipped kitchens, making them suitable for families or groups looking to enjoy a beach vacation.

Additionally, the nearby Rye Harbour area provides further options for vacation rentals, where visitors can find properties that combine coastal charm with modern comforts. Many houses here offer spacious living areas, outdoor barbeque facilities, and proximity to local shops and eateries, ensuring a comfortable stay.
What is the most popular type of vacation rental accomodation in Winchelsea?
In Winchelsea, cottages are the most popular type of vacation rental, with around 17 available in the area. These charming properties are often situated in picturesque locations, providing a homely atmosphere. Most cottages come equipped with fully furnished kitchens, comfortable living areas, and outdoor spaces such as gardens or patios, which are superb for enjoying the tranquil surroundings.
Are there any family house rentals in Winchelsea?
In Winchelsea, there are twelve family-friendly vacation rentals available, making it an excellent choice for families seeking a memorable getaway. This charming town, steeped in history, offers a variety of properties that cater to different needs. Many of these homes come with spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.

Visitors to Winchelsea will appreciate the proximity to beautiful beaches like Camber Sands, superb for a fun day out by the sea. Additionally, the town is close to the scenic landscapes of the Rye Harbour Nature Reserve, which provides opportunities for birdwatching and leisurely walks. Expect amenities such as Wi-Fi, gardens, and some properties may even feature game rooms or play areas, adding to the enjoyment for younger guests.
Can I rent a vacation home with a pool or hot tub in Winchelsea?
In Winchelsea, there are several vacation homes available for rent that feature pools and hot tubs. This picturesque village, located near the stunning East Sussex coastline, offers a charming backdrop for a relaxing getaway. Many of these properties come equipped with private pools, hot tubs, and outdoor living areas, superb for enjoying the tranquil surroundings. Additionally, travellers can expect amenities such as fully equipped kitchens, spacious living areas, and gardens, making these rentals ideal for families or groups looking to unwind.
Can I find long-stay vacation rentals in Winchelsea?
A long-stay vacation rental in Winchelsea is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winchelsea?
In Winchelsea, there are several pet-friendly house rentals available, with around twelve options to choose from. This charming historic town, located near the stunning coast of East Sussex, offers a variety of vacation homes that welcome pets, making it an ideal destination for travellers looking to bring their furry companions along.

Many of these rentals feature amenities such as spacious gardens or courtyards, allowing pets to enjoy the outdoors. Additionally, you can expect comfortable living spaces with fully equipped kitchens, cosy lounges, and modern bathrooms, ensuring a pleasant stay for all guests.
Are there any remote work vacation rentals in Winchelsea?
In Winchelsea, there are numerous vacation rentals suitable for remote work, with around 25 options available for travellers. This picturesque town, known for its charming medieval architecture and proximity to scenic coastal areas, offers a range of properties equipped with essential amenities for those working remotely. Expect to find rentals featuring reliable Wi-Fi and designated laptop workspace areas, ensuring a productive environment during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winchelsea vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winchelsea with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winchelsea?
In Winchelsea, popular vacation rental amenities include well-equipped kitchens, allowing guests to prepare their own meals with ease. Most rentals also come with cookware, dishware, and utensils, making it convenient for those who enjoy cooking. Additionally, many properties offer free Wi-Fi in the rooms, which is ideal for staying connected or planning local excursions. Many accommodations feature microwaves and ovens, suiting various cooking needs.
When is the best time to visit Winchelsea for a vacation rental?
The best time to visit Winchelsea for a vacation rental is during the peak season from June to August, with July being particularly popular among travellers. This vibrant period attracts those seeking a mix of coastal charm and historical exploration, as visitors flock to enjoy the warm summer weather and the picturesque beaches along the Sussex coast.

During these summer months, temperatures typically hover in the high teens to low twenties Celsius, creating a friendly space for outdoor activities such as cycling, walking, and leisurely strolls through the quaint streets lined with medieval architecture. The local events, including fairs and festivals, add to the lively spirit, making it an exciting time for families and friends alike.

If you're looking for a more budget-friendly option, consider visiting in November. This month offers a tranquil experience, superb for those who appreciate the beauty of autumn without the hustle and bustle of the peak season. Enjoy long walks on the beach, explore the nearby nature reserves, and immerse yourself in the local culture at a relaxed pace.
How early should I book a Winchelsea vacation rental?
Book your Winchelsea vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winchelsea?
In Winchelsea, visitors can immerse themselves in a rich historical experience. The town is renowned for its medieval architecture, including the impressive St. Thomas's Church, which features a striking bell tower and beautiful stained-glass windows. Nearby, the charming Winchelsea Beach offers a lovely coastal retreat, superb for leisurely walks along the shore and enjoying the natural scenery.
Can I change or cancel my Winchelsea home rental booking on Vrbo?
To find Winchelsea vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winchelsea vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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