Photo by Rob Parkin

Chailey holiday homes

We found 1,134 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:27 Nov - 4 Dec

Exceptional
(20 reviews)

17th Century Listed Self-Catering Cottage

Uckfield

9% off
NZ$4,617
for 7 nights, 1 cottage
NZ$660 per night
includes taxes & fees
17th Century Listed Self-Catering Cottage
Hand made kitchen units with granite worktops
The garden in late summer
Sitting area
Sitting/living area with woodburner
Exceptional
(46 reviews)

Deerkeepers Cottage - luxurious and contemporary rural retreat

East Grinstead

8% off
NZ$2,537
for 7 nights, 1 cottage
NZ$362 per night
includes taxes & fees
Deerkeepers Cottage - luxurious and contemporary rural retreat
Room
Living area
Private kitchen
Terrace/patio
Exceptional
(87 reviews)

Woodpeckers Cottage - One bedroom luxurious and Contemporary rural retreat

East Grinstead

9% off
NZ$2,038
for 7 nights, 1 cottage
NZ$291 per night
includes taxes & fees
Woodpeckers Cottage - One bedroom luxurious and Contemporary rural retreat
Interior
Living area
The Opulent Room: top floor front bedroom sleeps 5: 3 in single beds & 2 in bunk
More dining space views
Exceptional
(53 reviews)

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

Brighton

9% off
NZ$8,936
for 7 nights, 1 home
NZ$1,277 per night
includes taxes & fees
Central, stylish 4BRH, sleeps up to 20 people, couples to large groups welcome.
Cabin made up for two guests
Living area
Well-appointed Kitchenette
Room
Exceptional
(15 reviews)

Harlequin Cabin in East Sussex

Lewes

9% off
NZ$1,668
for 7 nights, 1 cabin
NZ$238 per night
includes taxes & fees
Harlequin Cabin in East Sussex
The garden - on right is the gate to the Common
Larch Cottage - in winter
The living area and kitchen
Kitchen area
Exceptional
(46 reviews)

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

Lewes

23% off
NZ$1,983
for 7 nights, 1 home
NZ$283 per night
includes taxes & fees
Modern Barn In The Heart Of Sussex, Easy access to Lewes and Brighton
Dining
Private kitchen
Exterior
Room
Exceptional
(8 reviews)

Large Central Delightful Townhouse with Garden

Brighton

9% off
NZ$6,167
for 7 nights, 1 home
NZ$881 per night
includes taxes & fees
Large Central Delightful Townhouse with Garden
Interior
Interior
Room
Private kitchen
Exceptional
(5 reviews)

Cosy house near centre of Haywards Heath.

Haywards Heath

18% off
NZ$2,542
for 7 nights, 1 home
NZ$363 per night
includes taxes & fees
Cosy house near centre of Haywards Heath.
Private kitchen
Dining
Living area
Interior
Exceptional
(39 reviews)

Delightful luxury bath and breakfast 3

Brighton

7% off
NZ$1,719
for 7 nights, 1 room
NZ$246 per night
includes taxes & fees
Delightful luxury bath and breakfast 3
Property grounds
Dining
Private kitchen
Interior
Exceptional
(29 reviews)

Stylish, Light-Filled Room with Private Bathroom in a Quiet Brighton Home

Brighton

7% off
NZ$1,688
for 7 nights, 1 home
NZ$241 per night
includes taxes & fees
Stylish, Light-Filled Room with Private Bathroom in a Quiet Brighton Home
Dining
Outdoor dining
Exterior detail
Living area
Exceptional
(96 reviews)

Central Sea View Penthouse with Private Roof Terraces

Brighton

13% off
NZ$3,125
for 7 nights, 1 apartment
NZ$446 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
NZ$2,750
for 7 nights, 1 apartment
NZ$393 per night
includes taxes & fees
Cosy Brighton Apt | Walk to Stations | Quiet Area
Living area
Property grounds
Interior
bedroom desk and vanity table
Exceptional
(73 reviews)

Central Beachfront Penthouse with private sun / roof terrace

Hove

9% off
NZ$2,304
for 7 nights, 1 apartment
NZ$329 per night
includes taxes & fees
Central Beachfront Penthouse with private sun / roof terrace
Living area
Living area
Exterior detail
Exterior detail
Very good
(7 reviews)

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

Brighton

9% off
NZ$2,531
for 7 nights, 1 apartment
NZ$362 per night
includes taxes & fees
MASON&FINN STAYS: Luxury 1-Bed Flat w Seaview
Fitness facility
Interior
Private kitchen
Outdoor dining
Exceptional
(34 reviews)

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

Brighton

9% off
NZ$2,282
for 7 nights, 1 apartment
NZ$326 per night
includes taxes & fees
Beautiful, luxury two bedroom apartment, within easy reach of the city centre,
Dining
Room
Living area
Excellent
(18 reviews)

Eclectic modern victorian large city central flat

Brighton

8% off
NZ$5,528
for 7 nights, 1 home
NZ$790 per night
includes taxes & fees
Eclectic modern victorian large city central flat
Interior
Dining
Private kitchen
Private kitchen
Exceptional
(28 reviews)

Stylish, Light-Filled Room with Private Bathroom in a Quiet Brighton Home

Brighton

7% off
NZ$1,679
for 7 nights, 1 home
NZ$240 per night
includes taxes & fees
Stylish, Light-Filled Room with Private Bathroom in a Quiet Brighton Home
  • 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, Bookabach 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 Bookabach. 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 Bookabach.
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 Bookabach 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 Bookabach, 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.