Photo by Rob Parkin

Chailey holiday rentals

We found 1,112 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Chailey that are perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the best amenities for spending time at your holiday home, such as parking and air conditioning. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Chailey

Showing deals for:25 Dec - 1 Jan

Stairs to large bedroom area
View from the deck
Fully equipped kitchen with dishwasher and washing machine
Large airy bedroom with king size bed, plenty of room for a cot if required
Exceptional
(113 reviews)

Comfortable Barn, Ashdown Forest, Fantastic Local Pub, Excellent For Walkers

Haywards Heath

9% off
AU$1,304
for 7 nights, 1 cottage
AU$186 per night
includes taxes & fees
Comfortable Barn, Ashdown Forest, Fantastic Local Pub, Excellent For Walkers
Terrace/patio
Living area
Room
Private kitchen
Exceptional
(90 reviews)

Woodpeckers Cottage - One bedroom luxurious and Contemporary rural retreat

East Grinstead

9% off
AU$2,205
for 7 nights, 1 cottage
AU$315 per night
includes taxes & fees
Woodpeckers Cottage - One bedroom luxurious and Contemporary rural retreat
Well-appointed Kitchenette
Living area
Room
Terrace/patio
Exceptional
(15 reviews)

Harlequin Cabin in East Sussex

Lewes

9% off
AU$1,626
for 7 nights, 1 cabin
AU$232 per night
includes taxes & fees
Harlequin Cabin in East Sussex
Kitchen area
Larch Cottage - in winter
The garden - on right is the gate to the Common
View from the garden
Exceptional
(46 reviews)

Modern Barn In The Heart Of Sussex, Easy access to Lewes and Brighton

Lewes

23% off
AU$1,626
for 7 nights, 1 home
AU$232 per night
includes taxes & fees
Modern Barn In The Heart Of Sussex, Easy access to Lewes and Brighton
Interior
Living area
More dining space views
The back of the living with 3 out 4 sofa beds
Exceptional
(53 reviews)

Central, stylish 4BRH, sleeps up to 20 people, couples to large groups welcome.

Brighton

9% off
AU$9,039
for 7 nights, 1 home
AU$1,291 per night
includes taxes & fees
Central, stylish 4BRH, sleeps up to 20 people, couples to large groups welcome.
Front room with sofa view
Kitchen view with breakfast bar
Main bedroom with velux window view
Regency building view
Exceptional
(13 reviews)

Cosy Brighton Apt | Walk to Stations | Quiet Area

Brighton

13% off
AU$3,247
for 7 nights, 1 apartment
AU$464 per night
includes taxes & fees
Cosy Brighton Apt | Walk to Stations | Quiet Area
Lounge
Patio/terrace
Lounge-small dining table overlooking street
Bedroom
Wonderful
(7 reviews)

Trendy Central 1 Bed Flat with Roof Terrace

Brighton

5% off
AU$2,222
for 7 nights, 1 apartment
AU$317 per night
includes taxes & fees
Trendy Central 1 Bed Flat with Roof Terrace
Private kitchen
Living area
Exterior detail
Living area
Very good
(7 reviews)

MASON&FINN STAYS: Luxury 1-Bed Flat w Seaview

Brighton

9% off
AU$2,124
for 7 nights, 1 apartment
AU$303 per night
includes taxes & fees
MASON&FINN STAYS: Luxury 1-Bed Flat w Seaview
Living area
Dining
Living area
Excellent
(18 reviews)

Eclectic modern victorian large city central flat

Brighton

9% off
AU$4,887
for 7 nights, 1 home
AU$698 per night
includes taxes & fees
Eclectic modern victorian large city central flat

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Chailey getaway

Learn about the unique charm of Chailey with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Chailey

Are you hoping to discover things to do in the area? Venture out of your holiday home and check out everything that makes Chailey a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • East Sussex National Golf Club (5.2 mi / 8.3 km)
  • Ockenden Manor Spa (6.6 mi / 10.6 km)
  • Bolney Estate Winery (9 mi / 14.4 km)
  • Royal Ashdown Forest Golf Club (9.2 mi / 14.8 km)
  • Tulley's Farm (11 mi / 17.8 km)
  • SEA LIFE Brighton (11.1 mi / 17.9 km)

Exploring the natural landscape of Chailey

Whether you're looking for adventure or just want to appreciate the scenery, Chailey is a great spot to appreciate mother nature. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Sheffield Park Garden (2.8 mi / 4.5 km)
  • Wakehurst Place (8.1 mi / 13 km)
  • Ashdown Forest (8.1 mi / 13.1 km)
  • Enchanted Place - Winnie the Pooh (9 mi / 14.4 km)
  • Nymans (10.1 mi / 16.2 km)
  • Devil's Dyke (10.1 mi / 16.3 km)

How to get to and around Chailey

The nearest airport is in Gatwick Airport (LGW), located 15.1 mi (24.3 km) from the city centre.

Frequently asked questions

What is the best area to stay in Chailey when booking a holiday rental?
When considering a holiday rental in Chailey, one of the most appealing areas to stay in is the charming neighbourhood surrounding the village centre. This area offers a delightful blend of rural tranquillity and easy access to local amenities. You'll find a variety of properties here, ranging from quaint cottages to modern family homes, making it suitable for different types of visitors.A key attraction nearby is the stunning Chailey Common, which is a designated Site of Special Scientific Interest. It provides ample opportunities for walking and enjoying the beautiful natural landscape, great for those who appreciate outdoor activities. Additionally, the historic St. Peter's Church adds a touch of heritage to the area, inviting visitors to explore its beautiful architecture and serene grounds.Staying in this neighbourhood not only places you within reach of these attractions but also ensures you can enjoy the peaceful village atmosphere that Chailey is known for.
What are the top attractions in Chailey?
In Chailey, visitors can enjoy a tranquil rural setting with several noteworthy attractions. The historic St. Peter's Church, with its beautiful architecture and serene churchyard, offers a glimpse into the area's past. Nature enthusiasts can explore the expansive Chailey Common, a Site of Special Scientific Interest, which features stunning heathland and diverse wildlife, great for walking and enjoying the outdoors.Nearby, the charming village of Cooksbridge boasts the picturesque River Ouse, ideal for riverside strolls and a peaceful atmosphere. For those interested in local history, the nearby National Trust property of Sheffield Park and Garden is a must-visit, showcasing beautiful landscaped gardens and woodlands.The area is also conveniently located near the South Downs National Park, offering breathtaking views and extensive walking trails for those who appreciate scenic landscapes and outdoor activities.
Are all fees included in the Chailey holiday homes prices shown on Stayz?
Stayz 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.
Are there any Chailey holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chailey 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 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.
Are there any discounts for Chailey holiday homes?
You can find great discounts on holiday homes in Chailey on Stayz, 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.
Can I change or cancel my Chailey holiday home booking on Stayz?
To find Chailey holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chailey?
A long-stay holiday home in Chailey 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chailey holiday home?
Book your Chailey holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chailey?
Prices for holiday homes in Chailey 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. Stayz offers something for every taste and budget, from affordable homes in Chailey to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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