Winchelsea holiday rentals

We found 657 holiday rentals — enter your dates for availability
Select from 14 homes, 22 cottages and other holiday rentals in Winchelsea to find one that's perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the amenities that you need and want for your stay, which might include a garden and Wi-Fi. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Winchelsea

Showing deals for:6 Nov - 13 Nov

Living area
Interior
Dining
Pool
Exceptional
(16 reviews)

Countryside House Near Battle

Battle

9% off
AU$6,363
for 7 nights, 1 room
AU$909 per night
includes taxes & fees
Countryside House Near Battle
Private kitchen
Interior
Private kitchen
Beach
Exceptional
(50 reviews)

Stunning Spacious Seaside cottage, 1 minute from the beach sleeps 12

Rye

44% off
AU$3,786
for 7 nights, 1 cottage
AU$541 per night
includes taxes & fees
Stunning Spacious Seaside cottage, 1 minute from the beach sleeps 12
Private kitchen
Dining
Living area
Living area
Exceptional
(73 reviews)

Converted barn / Oast House with amazing views and EV chargers

Rye

28% off
AU$4,830
for 7 nights, 1 home
AU$690 per night
includes taxes & fees
Converted barn / Oast House with amazing views and EV chargers
Dinging Room and Snug.
Real fire in the cosy lounge
Ktchen
Interior
Exceptional
(102 reviews)

Spacious 4 Star Period Cottage, log fire, large garden, countryside, near Rye

Rye

35% off
AU$2,349
for 7 nights, 1 cottage
AU$336 per night
includes taxes & fees
Spacious 4 Star Period Cottage, log fire, large garden, countryside, near Rye
Beach
Living area
Exterior
Dining
Exceptional
(59 reviews)

Beautiful Seaside Cottage 1 minute from the beach - The Tides

Rye

50% off
AU$4,487
for 7 nights, 1 cottage
AU$641 per night
includes taxes & fees
Beautiful Seaside Cottage 1 minute from the beach - The Tides
Master bedroom with large double bed and sea views and private balcony
Interior
Beach side
Dining
Exceptional
(41 reviews)

"Seacrest" Camber - beachside property with uninterupted sea views

Rye

21% off
AU$5,900
for 7 nights, 1 home
AU$843 per night
includes taxes & fees
"Seacrest" Camber - beachside property with uninterupted sea views
Property grounds
View of The Retreat from garden.
Exterior
Interior
Exceptional
(62 reviews)

Tranquil Retreat, Two Bedrooms, Two Bathrooms (one en-suite, one shower room)

Hastings

9% off
AU$1,819
for 7 nights, 1 cottage
AU$260 per night
includes taxes & fees
Tranquil Retreat, Two Bedrooms, Two Bathrooms (one en-suite, one shower room)
Living area
Terrace/patio
Dining
Interior
Excellent
(7 reviews)

Boutique, interior designed, historic property

Rye

13% off
AU$4,684
for 7 nights, 1 home
AU$669 per night
includes taxes & fees
Boutique, interior designed, historic property
The flat's glass balustrade balcony and back garden of the property
hot tub
pool
path to pool
Exceptional
(27 reviews)

Sea View Studio Flat with heated indoor pool & spa, countryside location

Hastings

30% off
AU$976
for 7 nights, 1 apartment
AU$139 per night
includes taxes & fees
Sea View Studio Flat with heated indoor pool & spa, countryside location
Stone Green Oast - opens onto the enclosed, pet friendly garden
The Cinque Port market town of Tenterden is close by
The dining area is an architect-designed mix of old and new oak
The view from the front door across the neighbouring garden
Exceptional
(136 reviews)

Delightful pet-friendly oast with enclosed garden on Kent/Sussex border near Rye

Tenterden

9% off
AU$2,016
for 7 nights, 1 cottage
AU$288 per night
includes taxes & fees
Delightful pet-friendly oast with enclosed garden on Kent/Sussex border near Rye
One corner of our living room...
The garden is part of the living room...
A view of the dunes from our sunny back garden and bedrooms
The Dunes Bedroom can be arranged either as a kingsize or as 2 singles
Exceptional
(38 reviews)

Looney Dunes, Camber - 1 min to sand dunes, 2 sunny gardens, 3 bedrooms

Rye

19% off
AU$3,279
for 7 nights, 1 home
AU$468 per night
includes taxes & fees
Looney Dunes, Camber - 1 min to sand dunes, 2 sunny gardens, 3 bedrooms
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Why visit Winchelsea

  • Historic Architecture: Discover Winchelsea's stunning medieval buildings and charming streets that reflect its rich history.
  • Beautiful Beaches: Relax on the local beach, enjoying the scenic coastline and tranquil atmosphere.
  • Outdoor Activities: Explore picturesque reserves and indulge in various outdoor pursuits in the surrounding countryside.
  • Cultural Festivals: Attend the vibrant Winchelsea Medieval Festival for a taste of local culture and history.
  • Wine Tasting: Enjoy delightful experiences at nearby wineries, perfect for wine enthusiasts.

Popular types of accommodation in Winchelsea

Discover the charm of Winchelsea, a picturesque town in England steeped in history. Known for its stunning medieval architecture and scenic countryside, Winchelsea offers a delightful array of holiday rentals, including cosy cottages, private holiday homes, and comfortable apartments. Whether you seek accessible accommodation or a place with ample rooms, you will find a range of options to suit your needs. Experience the tranquillity and beauty of Winchelsea, where every stay promises a memorable getaway.

  • Cottages: Renowned for their charm, cottages are the top choice for visitors seeking a quintessentially English experience during their stay in Winchelsea.
  • Private Holiday Homes: Offering a home-away-from-home feel, private holiday homes are a popular option for those wanting more space and privacy.
  • Apartments: Ideal for couples or small groups, apartments provide convenient amenities and a central location for exploring the area.
  • Cabins: Emphasising a connection with nature, cabins offer a serene retreat amidst the countryside for a peaceful getaway.
  • Guest Houses: Providing a warm and welcoming atmosphere, guest houses are a lovely choice for those looking for a more personalised stay.**

Top attractions in and around Winchelsea

Winchelsea, England, is a charming destination perfect for those seeking beach, scenic views, and outdoor activities. Visitors can explore historic churches, enjoy the local beach, and experience the vibrant Winchelsea Medieval Festival. A short walk from the town centre leads to picturesque reserves, while nearby wineries offer delightful tasting experiences. This quaint town promises a blend of culture and family-friendly adventures for all who visit.

  • Winchelsea Beach: Enjoy the laid-back beach vibes along Winchelsea’s sandy shores, perfect for a leisurely stroll and seaside relaxation.
  • Great Dixter House and Gardens: Explore the historic House nestled 11km away, celebrated for its rich cultural heritage and magnificent garden displays.
  • Hastings Castle: Visit the evocative ruins, situated 11km from Winchelsea, offering a glimpse into the area’s storied past and cultural legacy.

Things to do recommended for couples

Discover charming Winchelsea with scenic walks along historic lanes and cosy evenings in quaint local pubs. Savour delightful meals and enjoy intimate moments in a picturesque setting perfect for a couple's retreat.

Things to do recommended for families

In Winchelsea, families will delight in exploring quaint markets and scenic coastal walks, while children revel in interactive local museum exhibits and charming countryside adventures.

Things to do recommended for groups

Embark on an adventure at Go Ape at Bedgebury, a zipline and ropes course located 26km from Winchelsea. Enjoy the thrill of the outdoor experience with your group, perfect for those seeking a lively and adventurous day out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

Whether you're journeying with a group, as a family, with your pets, or seeking extended stays, ensure you select the appropriate filters. Here are some Stayz booking suggestions for you.

  • Traveling to Winchelsea with a group: Consider how many bedrooms you require, along with facilities such as a fully-equipped kitchen or an outdoor area for group get-togethers. Luckily, you can refine your search for all of these features, and more, on Stayz.
  • Traveling to Winchelsea with young kids: Traveling with young children can present its challenges. It is essential to prioritise their comfort and safety, and ensure that age-appropriate amenities, such as a private swimming pool, are available. Additionally, it is worthwhile to consider the location in relation to attractions that are suitable for families.
  • Taking your pets with you to Winchelsea: For many, a family holiday isn’t complete without their four-legged companion. If this resonates with you, explore Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels right at home.
  • Planning for a long term stay visiting Winchelsea: If you're seeking holiday rentals with special offers for monthly stays, you've come to the right place. With the appropriate filter, you can effortlessly discover and save on long-term rentals. You might also consider including a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Winchelsea

Winchelsea offers a delightful blend of beachside charm and scenic landscapes. Explore its inviting coastline and relax on the beach while enjoying the friendly, historical atmosphere. The convenient location makes it easy to immerse yourself in the city’s relaxed vibe, with picturesque views just a short distance away. Perfect for a family-friendly, budget holiday, Winchelsea promises a memorable outdoor experience amidst its quaint and welcoming surroundings.

  • Rye: Rye is a historic city located 3km from Winchelsea, known for its captivating blend of coastal charm and scenic countryside. Visitors are drawn to Rye for its excellent beach, outdoor pursuits, and picturesque landscapes. The area offers a variety of recreational activities including golf on well-maintained courses, and its proximity to family-friendly beaches and dunes ensures a memorable experience for all ages.
  • Hastings: Hastings, a vibrant city 13km from Winchelsea, presents a delightful mix of outdoor adventures and coastal allure. The city is well-regarded for its extensive beaches, scenic views, and outdoor lifestyle. Explore its recreational areas, enjoy a theatrical performance, or try your hand at golf. Hastings’ charming coastal attractions, including its family beach and dune landscapes, provide a refreshing escape for visitors.
  • Camber: Camber, a quaint village situated 6km from Winchelsea, offers a serene retreat for those seeking coastal beauty and outdoor activities. This destination is celebrated for its beautiful beaches and scenic surroundings, making it ideal for leisurely walks along hiking trails. Enjoy the local recreational areas or indulge in a relaxing spa experience, all while taking in the stunning views of the family beach and dune landmarks that define this charming locale.

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 CloudyAverageSlightly Low
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 SunnyAverageAverage
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 Stayz is a breeze

Looking to save money on your next holiday? It might be worth considering some flexibility with your travel dates, as prices can vary. Moreover, booking a longer stay often leads to significant savings. To find the ideal Stayz property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s Trip Board offers a user-friendly platform where you can effortlessly plan new trips, resume previous ones, or manage your travel arrangements. You’ll discover your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Travel to friendly Winchelsea

The area's churches and monuments are just some of the reasons to come on holiday to Winchelsea. This welcoming and relaxing city entices travellers with its restaurants and gardens. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Winchelsea

Are you hoping to discover top things to see and do during your stay? Venture out of your holiday home and check out everything that makes Winchelsea a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 an active traveller or just want to appreciate the scenery, Winchelsea is a great place to get outside. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Winchelsea Beach (1.2 mi / 2 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)
  • Great Dixter House and Gardens (7.1 mi / 11.4 km)
  • Hastings Beach (7.8 mi / 12.6 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 centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Winchelsea?
Cottages are the most popular kind of holiday home in Winchelsea, according to our data. Even if you have something a little different in mind, Stayz has properties in a variety of sizes and shapes. Filter our options to find your ideal match.
How much does it cost to rent a holiday home in Winchelsea?
Season, length of stay and property type are some things that can influence the price of a holiday home. Simply add your travel dates to find your ideal match. From comfy cabins to expansive villas, all Stayz holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Winchelsea?
The average price for a holiday home close to the beach in Winchelsea will depend on when you'll be there and the size and type of property you're searching for. You can find prices quickly and easily on Stayz by entering your destination and travel dates. Then make use of the filter tool to choose the number of bedrooms and amenities that you need, like WiFi, air conditioning and a hot tub.
Are there pet-friendly holiday homes in Winchelsea?
With 53 holiday homes that allow pets, your happy hound can join in the fun on your Winchelsea break. Use the filter tool to search our pet-friendly holiday homes and find the pawfect pad on Stayz.
Can I rent a house with a pool in Winchelsea?
Add another level of fun to your getaway by booking one of the three houses with a private pool in Winchelsea. Use our search filter to find properties with pools on Stayz, then spend leisurely days frolicking in a swimming pool that's for your exclusive use.
What are popular home amenities in Winchelsea?
A firepit, tennis and a fireplace are rated the most popular home amenities in Winchelsea. Whether you're taking to the road solo, with your spouse or a group of friends, Stayz can help you find a holiday home that suits your tastes with all the options you need.
Are there large group holiday homes in Winchelsea?
Take your pick of 25 Stayz holiday properties in Winchelsea that can host five or more people. You'll enjoy all the space and privacy you need to have fun with the people you're holidaying with — and no one else.
Are there holiday homes in Winchelsea that welcome kids?
Winchelsea has 53 family-friendly holiday homes to pick from. And finding a stay that welcomes children is a cinch with our "Properties good for families" filter. In addition to having the whole place to yourselves, you'll also enjoy access to perks and amenities like dining rooms, kitchens and private pools.
What are the top attractions for families in Winchelsea?
Keep your kids occupied at these fun family-friendly attractions in Winchelsea:
  • Camber Sands
  • Hastings Pier
  • Winchelsea Beach
Are there one-bedroom holiday homes in Winchelsea?
Yes, Winchelsea has eight one-bedroom homes available. Typically situated in well-regarded areas due to their compact size, a one-bedroom holiday property is perfect if you're travelling with a pal or your partner. And with comforts such as laundry facilities and more privacy than a standard hotel, you'll be able to chill out while exploring this awesome destination.
Can I find two-bedroom holiday homes in Winchelsea?
Winchelsea has 30 two-bedroom holiday properties for you to select from. Experience a holiday home with all the comfort and space you need at a price you'll love on Stayz.
Are there holiday homes with WiFi in Winchelsea?
You can pick from 16 holiday homes with WiFi in Winchelsea. If you want to disconnect from the world on your escape, but still need to be connected to the internet, these properties have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How old do you have to be to rent a holiday home in Winchelsea?
It's advisable to check with the Winchelsea holiday property you want on Stayz as age restrictions vary. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Winchelsea for?
The amount of time you can book a Winchelsea holiday home for differs depending on the property. Simply put in your travel dates to view options that offer extended stays. They come with the things you need to make your extended trip more enjoyable and comfortable, such as kitchens and yards. Some holiday homes may also offer discounted weekly or monthly prices, so you can have a longer stay for less.

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