Winchelsea holiday lettings

We found 752 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in Winchelsea that are 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.
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  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

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)
  • 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 centre.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Winchelsea?
Cottages are the most popular kind of holiday rental in Winchelsea, according to our data. Even if you have something a little different in mind, Vrbo 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 rental 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 Vrbo holiday rentals 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 Vrbo 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 rentals in Winchelsea?
With 53 holiday rentals 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 rentals and find the pawfect pad on Vrbo.
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 Vrbo, then spend leisurely days frolicking in a swimming pool that’s for your exclusive use.
What are popular rental amenities in Winchelsea?
A firepit, tennis and a fireplace are rated the most popular rental amenities in Winchelsea. Whether you’re taking to the road solo, with your spouse or a group of friends, Vrbo can help you find a holiday rental that suits your tastes with all the options you need.
Are there large group holiday rentals in Winchelsea?
Take your pick of 25 Vrbo 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 rentals 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 rentals in Winchelsea?
Yes, Winchelsea has eight one-bedroom rentals 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 rentals 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 Vrbo.
Are there holiday rentals with WiFi in Winchelsea?
You can pick from 16 holiday rentals 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 Vrbo.
How old do you have to be to rent a holiday rental in Winchelsea?
It’s advisable to check with the Winchelsea holiday property you want on Vrbo as age restrictions vary. However, generally it’s 16, 18 or 21.
How long can I rent a holiday rental 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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