A vintage steam locomotive with the number 92212 on its front.

Chailey Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chailey holiday rentals

A balcony with a white metal table and two chairs, a striped sofa, and a wooden railing.

1. 1 Bed Flat - Sleeps 2 - Pets - Garden - Parking

1 Bed Flat - Sleeps 2 - Pets - Garden - Parking
3.0 star property
Lewes
8.6 out of 10, Excellent, (10 reviews)
"Lovely, cosy, quirky little place in a very quiet part of town. It has everything I needed for my stay. Only stayed 1 night for work purposes but wanted to stay longer. Rod was very welcoming and throughly nice chap."
United Kingdom
Phill
The price is RM431
RM431 total
includes taxes & fees
29 Sept - 30 Sept
1 Bed Flat - Sleeps 2 - Pets - Garden - Parking
A cozy lodge entrance with a sign reading 'Duck Lodge,' a small outdoor seating area, and a pathway leading to the entrance.

2. Duck Lodge B&B

Duck Lodge B&B
3.0 star property
Brighton
10.0 out of 10, Exceptional, (26 reviews)
"Amazing host, and the lodge was absolutely spotless "
United Kingdom
Meredith
The price is RM691
RM829 total
includes taxes & fees
12 Oct - 13 Oct
Duck Lodge B&B
A modern lobby with a reception desk, seating area, and a staircase leading to upper floors.

3. Charles Hope Hove

Charles Hope Hove
3.5 star property
Hove
8.6 out of 10, Excellent, (37 reviews)
"Really nice apartment in a good location, super clean, well equipped and great WiFi. Parking allocation is a bit of a faff along with first time entry, ideally they need to allow you to book parking along with the room. It's the fifth time I've stayed, so they are doing something right 👍"
United Kingdom
Mike
The price is RM482
RM578 total
includes taxes & fees
19 Oct - 20 Oct
Charles Hope Hove

4. Orchard View Shepherds Hut

Orchard View Shepherds Hut
2.0 star property
Henfield
The price is RM605
RM726 total
includes taxes & fees
29 Sept - 30 Sept
Orchard View Shepherds Hut
A historic building with three arched windows and two green doors, numbered 24 and 22.

5. Cliffe Cottage

Cliffe Cottage
3.5 star property
Lewes
The price is RM2,546
RM3,055 total
includes taxes & fees
2 Oct - 3 Oct
Cliffe Cottage
A wooden exterior with a pergola, a small potted plant, and a grey sofa.

6. Lodge , air con , Free Parking , Mini bar

Lodge , air con , Free Parking , Mini bar
3.0 star property
Hove
10.0 out of 10, Exceptional, (12 reviews)
"Very welcoming and well thought out accommodation. Would definitely stay again "
United Kingdom
Sally
The price is RM569
RM667 total
includes taxes & fees
4 Oct - 5 Oct
Lodge , air con , Free Parking , Mini bar
A neatly arranged bedroom with a bed, a bedside table with a lamp, a hanging clothes rack, a mirror, and a painting on the wall.

7. Upper Rock Brighton Apartments

Upper Rock Brighton Apartments
3.0 star property
Kemptown
9.8 out of 10, Exceptional, (55 reviews)
"Location and amenities were excellent, as was the helpfulness and communication from hosts."
United Kingdom
Samantha
The price is RM375
RM612 total
includes taxes & fees
1 Oct - 2 Oct
Upper Rock Brighton Apartments
A bedroom with a bed, two heart-shaped mirrors, and a door.

8. Brighton Abode by Brighton Holiday Lets

Brighton Abode by Brighton Holiday Lets
3.0 star property
Brighton
10.0 out of 10, Exceptional, (1 review)
"I had a really amazing time when I stayed at this property and was pleasantly surprised with everything that it had to offer. Both my partner and I had a wonderful, cosy experience and believe it was an absolute bargain for everything that you get! 10/10 :)"
United Kingdom
MWANSA
The price is RM696
RM696 total
includes taxes & fees
28 Sept - 29 Sept
Brighton Abode by Brighton Holiday Lets
A rooftop terrace with a view of the city skyline, outdoor seating, and a potted plant arrangement.

9. Q Square by Supercity Aparthotels

Q Square by Supercity Aparthotels
4.0 star property
Brighton City Centre
9.6 out of 10, Exceptional, (388 reviews)
"Lovely staff, great location. Would recommend"
Canada
Estrella Leila
The price is RM352
RM423 total
includes taxes & fees
4 Oct - 5 Oct
Q Square by Supercity Aparthotels

10. Artists Hideaway in Cowfold

Artists Hideaway in Cowfold
3.0 star property
Horsham
The price is RM771
RM925 total
includes taxes & fees
1 Oct - 2 Oct
Artists Hideaway in Cowfold
A hotel room with a bed, bedside tables, a wardrobe, a mirror, and artwork on the walls.

11. Numa Brighton Pavilion

Numa Brighton Pavilion
4.0 star property
Brighton City Centre
8.2 out of 10, Very good, (1,127 reviews)
"Very pleasant stay"
United Kingdom
Daniel
The price is RM378
RM454 total
includes taxes & fees
6 Oct - 7 Oct
Numa Brighton Pavilion
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chailey Hotel Reviews

Sofitel London Gatwick

Sofitel London Gatwick

10/10 Excellent
"Perfect location for an early flight."
Sylvie 1-night trip
Posted 1 hour ago
Sofitel London Gatwick

Find out more about Chailey

Search for holiday rentals in Chailey on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Chailey using one of the methods below:

  • View our selection of featured holiday rentals in Chailey
  • Use the map to find apartments and other holiday homes in the Chailey neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chailey while they last

Look no further and take a look at our great range of rental properties in Chailey!

Frequently asked questions

Are there holiday rentals in Chailey?

Yes, there are holiday rentals in Chailey close to Bluebell Railway - Sheffield Park Station, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Chailey?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Chailey stay.

What can I see and do in Chailey?

While exploring the area, visit family-friendly sights like Tulley's Farm, or get outside and enjoy nature at High Weald. In the wider area, you’ll find Bluebell Railway - Sheffield Park Station and Sheffield Park Garden.

What are holiday rentals like in Chailey?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chailey. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family gatherings.