Photo by Rob Parkin

Chailey holiday rentals

We found 1,111 holiday rentals — enter your dates for availability
Discover a selection of 6 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:13 Nov - 20 Nov

Exceptional
(20 reviews)

17th Century Listed Self-Catering Cottage

Uckfield

9% off
AU$3,774
for 7 nights, 1 cottage
AU$539 per night
includes taxes & fees
17th Century Listed Self-Catering Cottage
King size bed
Exterior
Living area
Fully equipped kitchen
Exceptional
(20 reviews)

Beautiful contemporary accommodation - Sleeps 2 adults

Lewes

9% off
AU$1,455
for 7 nights, 1 cottage
AU$208 per night
includes taxes & fees
Beautiful contemporary accommodation - Sleeps 2 adults
Living area
Living area
Private kitchen
Dining
Exceptional
(20 reviews)

Luxury Mansion Townhouse with Private Cinema sleeping up to 18

Brighton

9% off
AU$13,565
for 7 nights, 1 home
AU$1,938 per night
includes taxes & fees
Luxury Mansion Townhouse with Private Cinema sleeping up to 18
Room
Living area
Private kitchen
Exterior
Exceptional
(87 reviews)

Woodpeckers Cottage - One bedroom luxurious and Contemporary rural retreat

East Grinstead

9% off
AU$1,719
for 7 nights, 1 cottage
AU$246 per night
includes taxes & fees
Woodpeckers Cottage - One bedroom luxurious and Contemporary rural retreat
Large airy bedroom with king size bed, plenty of room for a cot if required
View from the deck
Fully equipped kitchen with dishwasher and washing machine
Stairs to large bedroom area
Exceptional
(111 reviews)

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

Haywards Heath

9% off
AU$1,324
for 7 nights, 1 cottage
AU$189 per night
includes taxes & fees
Comfortable Barn, Ashdown Forest, Fantastic Local Pub, Excellent For Walkers
Living area
Property grounds
King size Hypnos bed, overlooks garden
Property grounds
Exceptional
(51 reviews)

Peaceful edge-of-village C18th converted cottage in gardens of Manor House

Lewes

9% off
AU$2,662
for 7 nights, 1 cottage
AU$380 per night
includes taxes & fees
Peaceful edge-of-village C18th converted cottage in gardens of Manor House
Well-appointed Kitchenette
Living area
Cabin made up for two guests
Terrace/patio
Exceptional
(15 reviews)

Harlequin Cabin in East Sussex

Lewes

9% off
AU$1,391
for 7 nights, 1 cabin
AU$199 per night
includes taxes & fees
Harlequin Cabin in East Sussex
The back of the living with 3 out 4 sofa beds
Living area
Interior
More dining space views
Exceptional
(52 reviews)

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

Brighton

9% off
AU$7,455
for 7 nights, 1 home
AU$1,065 per night
includes taxes & fees
Central, stylish 4BRH, sleeps up to 20 people, couples to large groups welcome.
Dining
Private kitchen
Living area
Room
Exceptional
(8 reviews)

Large Central Delightful Townhouse with Garden

Brighton

9% off
AU$5,427
for 7 nights, 1 home
AU$775 per night
includes taxes & fees
Large Central Delightful Townhouse with Garden
Kitchen area
Larch Cottage - in winter
View from the garden
The garden - on right is the gate to the Common
Exceptional
(46 reviews)

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

Lewes

23% off
AU$1,651
for 7 nights, 1 home
AU$236 per night
includes taxes & fees
Modern Barn In The Heart Of Sussex, Easy access to Lewes and Brighton
Room
Interior
Private kitchen
Private kitchen
Exceptional
(5 reviews)

Cosy house near centre of Haywards Heath.

Haywards Heath

18% off
AU$2,170
for 7 nights, 1 home
AU$310 per night
includes taxes & fees
Cosy house near centre of Haywards Heath.
Interior
Dining
Relax in the sun
Interior
Exceptional
(60 reviews)

Beautiful, luxury two bedroom apartment, within easy reach of the city centre,

Brighton

9% off
AU$1,893
for 7 nights, 1 apartment
AU$270 per night
includes taxes & fees
Beautiful, luxury two bedroom apartment, within easy reach of the city centre,
Interior
Dining
Interior
Living area
Exceptional
(39 reviews)

Delightful luxury bath and breakfast 3

Brighton

7% off
AU$1,384
for 7 nights, 1 room
AU$198 per night
includes taxes & fees
Delightful luxury bath and breakfast 3
Private kitchen
Dining
Private kitchen
Interior
Exceptional
(49 reviews)

A calm haven in the heart of Brighton

Brighton

7% off
AU$1,436
for 7 nights, 1 room
AU$205 per night
includes taxes & fees
A calm haven in the heart of Brighton
Dining
Outdoor dining
Exterior detail
Living area
Exceptional
(95 reviews)

Central Sea View Penthouse with Private Roof Terraces

Brighton

13% off
AU$2,748
for 7 nights, 1 apartment
AU$393 per night
includes taxes & fees
Central Sea View Penthouse with Private Roof Terraces
Main bedroom with velux window view
Kitchen view with breakfast bar
Front room with dining table view
Front room with sofa view
Exceptional
(13 reviews)

Cosy Brighton Apt | Walk to Stations | Quiet Area

Brighton

13% off
AU$2,266
for 7 nights, 1 apartment
AU$324 per night
includes taxes & fees
Cosy Brighton Apt | Walk to Stations | Quiet Area
Interior
Property grounds
Living area
bedroom desk and vanity table
Exceptional
(73 reviews)

Central Beachfront Penthouse with private sun / roof terrace

Hove

8% off
AU$2,050
for 7 nights, 1 apartment
AU$293 per night
includes taxes & fees
Central Beachfront Penthouse with private sun / roof terrace
Bedroom
Patio/terrace
Lounge-small dining table overlooking street
Kitchen/Lounge
Wonderful
(7 reviews)

Trendy Central 1 Bed Flat with Roof Terrace

Brighton

5% off
AU$1,698
for 7 nights, 1 apartment
AU$243 per night
includes taxes & fees
Trendy Central 1 Bed Flat with Roof Terrace
Dining
Living area
Living area
Excellent
(18 reviews)

Eclectic modern victorian large city central flat

Brighton

8% off
AU$4,642
for 7 nights, 1 home
AU$663 per night
includes taxes & fees
Eclectic modern victorian large city central flat
fully equipped Kitchen
Twin bedroom bunk bed, top bed view
Kitchen and dining area
Front door pink with code access lock
Exceptional
(9 reviews)

Castle Bank Terrace - just a few minutes walk to the high street

Lewes

8% off
AU$2,740
for 7 nights, 1 home
AU$391 per night
includes taxes & fees
Castle Bank Terrace - just a few minutes walk to the high street
Private kitchen
Living area
Exterior detail
Exterior detail
Very good
(6 reviews)

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

Brighton

9% off
AU$2,150
for 7 nights, 1 apartment
AU$307 per night
includes taxes & fees
MASON&FINN STAYS: Luxury 1-Bed Flat w Seaview

  • 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)
  • Tulley's Farm (11 mi / 17.8 km)
  • SEA LIFE Brighton (11.1 mi / 17.9 km)
  • Brighton Pier (11.2 mi / 18 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:

  • Brighton Beach (11 mi / 17.8 km)
  • Sheffield Park Garden (2.8 mi / 4.5 km)
  • Borde Hill Garden (6.1 mi / 9.9 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)

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 most popular type of holiday home accommodation in Chailey?
Barns are the most popular kind of holiday home in Chailey, according to our data. Even if you've got something bigger or smaller in mind, Stayz has holiday homes in loads of shapes and sizes. Explore our options to find your ideal fit.
How much does it cost to rent a holiday home in Chailey?
The average price for a holiday home in Chailey can vary based on factors like length of stay, season and property type. Whether you're looking for a sprawling villa with a pool or a cosy cottage perfect for just you and the kids, just enter your travel dates to discover stays with amazing value.
How much does it cost to rent a beach house in Chailey?
When you travel and the size and style of the property will influence how much you'll pay for your beachside holiday home. Click on your Chailey travel dates to see all your options on Stayz. Can't live without a hot tub? Use our filters to select the amenities and features you want in your home.
Are there pet-friendly holiday homes in Chailey?
Good news! Yes. You can choose from two holiday homes that allow pets in Chailey. Many of our pet-friendly holiday homes come with an area outdoors for your four-legged friend to play in, special dog beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your place on Stayz.
What are popular home amenities in Chailey?
When it comes to home amenities that guests are looking for in Chailey, a firepit, nearby museums and a fireplace are at the top of the list. With Stayz holiday homes, there are choices to suit your taste and style, whether you're on a trip with family, friends or even pets.
Are there holiday homes in Chailey that welcome kids?
With two family-friendly holiday properties to choose from in Chailey, now is a great time to introduce your little ones to the magic of travel. Check our "Properties good for families" filter box to discover stays that come with conveniences ideal for families on the move, like full kitchens, backyards, entertainment areas and hot tubs.
What are the top attractions for families in Chailey?
There's a ton of awesome things to see and do with the family in Chailey, such as:
  • Lewes Castle
  • Barbican House Museum
  • Spring Barn Farm Park
How old do you have to be to rent a holiday home in Chailey?
The minimum age is usually 16, 18 or 21. It can change from property to property on Stayz, so check the rules of your chosen Chailey holiday home before booking your trip.
How long can I rent a holiday home in Chailey for?
The length of time you can book a holiday home in Chailey depends on the property. Just enter your preferred dates to look at a list of options offering extended stays. With loads of amenities such as laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get somewhere perfect to call your home away from home in Chailey.

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