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

Chailey Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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 S$135
includes taxes & fees
14 Oct - 15 Oct
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, (27 reviews)
"The accommodation was beautiful and every detail was catered for. The host was so helpful and couldn't do enough for us. Breakfast was ordered and they delivered it in the morning. The food was delicious The hot tub was brilliant. The location was brilliant as we wanted to walk in the surrounding area"
United Kingdom
Paul
The price is S$260
includes taxes & fees
9 Nov - 10 Nov
Duck Lodge B&B
A brick wall with a potted plant and flowers.

3. Newstead Farmhouse

Newstead Farmhouse
3.0 star property
Lewes
The price is S$1,127
includes taxes & fees
31 Oct - 1 Nov
Newstead Farmhouse
A rooftop terrace with a view of the city skyline, outdoor seating, and a potted plant arrangement.

4. Q Square by Supercity Aparthotels

Q Square by Supercity Aparthotels
4.0 star property
Brighton City Centre
9.6 out of 10, Exceptional, (394 reviews)
"Central location to everywhere and great facility to dine in or dine out. Clean and reasonable costs."
United States
Warren
The price is S$153
includes taxes & fees
14 Oct - 15 Oct
Q Square by Supercity Aparthotels
A hotel room with a bed, bedside tables, a wardrobe, a mirror, and artwork on the walls.

5. Numa Brighton Pavilion

Numa Brighton Pavilion
4.0 star property
Brighton City Centre
8.2 out of 10, Very good, (1,137 reviews)
"This is a great hotel in a great location,"
United Kingdom
Roshan
The price is S$128
includes taxes & fees
22 Oct - 23 Oct
Numa Brighton Pavilion
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.

6. Upper Rock Brighton Apartments

Upper Rock Brighton Apartments
3.0 star property
Kemptown
9.8 out of 10, Exceptional, (55 reviews)
"This is a small but well appointed 1 bedroom apartment situated 10 minutes stroll from the pier. There is a convenience store a couple of doors away and loads of cafes and restaurants nearby so excellently located."
United Kingdom
Alan
The price is S$162
includes taxes & fees
12 Nov - 13 Nov
Upper Rock Brighton Apartments
A bar area with a curved counter, multiple seating options, and a variety of plants and decorations.

7. City Heart Brighton

City Heart Brighton
3.0 star property
Brighton City Centre
9.0 out of 10, Wonderful, (42 reviews)
"Great location"
United Kingdom
Stephen
The price is S$145
includes taxes & fees
2 Nov - 3 Nov
City Heart Brighton
A bunk bed with a patterned sofa, a table with a bowl and plates, and a potted plant.

8. Hangover Hotel

Hangover Hotel
2.0 star property
Brighton City Centre
2.8 out of 10, (10 reviews)
"Top marks on all counts"
United States
Donald
The price is S$112
includes taxes & fees
13 Oct - 14 Oct
Hangover Hotel
A modern bedroom with a large bed, a bedside table, a mirror, and a wall-mounted light fixture.

9. Studio In the Lanes

Studio In the Lanes
3.0 star property
Brighton City Centre
9.0 out of 10, Wonderful, (12 reviews)
"Beautiful studio in an absolute excellent location. Can’t wait to come back!!"
United States
Genevieve
The price is S$148
includes taxes & fees
2 Nov - 3 Nov
Studio In the Lanes
Property grounds

10. Orchard View Shepherds Hut

Orchard View Shepherds Hut
2.0 star property
Henfield
The price is S$210
includes taxes & fees
19 Oct - 20 Oct
Orchard View Shepherds Hut
A wooden exterior with a pergola, a small potted plant, and a grey sofa.

11. 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 S$211
includes taxes & fees
18 Oct - 19 Oct
Lodge , air con , Free Parking , Mini bar
A hotel room with a bed, two armchairs, a small round table with a vase of flowers, and a view of the outdoors through large windows with curtains.

12. Osborne Apartments

Osborne Apartments
2.5 star property
Eastbourne
8.8 out of 10, Excellent, (154 reviews)
"Very spacious apartment with everything you require to make your stay comfortable. Have booked to return again several times this year. Great for someone working away for several days"
United Kingdom
Melvyn Spencer
The price is S$125
includes taxes & fees
13 Oct - 14 Oct
Osborne Apartments
A historic building with three arched windows and two green doors, numbered 24 and 22.

13. Cliffe Cottage

Cliffe Cottage
3.5 star property
Lewes
The price is S$959
includes taxes & fees
25 Oct - 26 Oct
Cliffe Cottage
A modern living room with a glass dining table, a sofa, a TV, and a view through a glass door to an outdoor area.

14. Brighton Courtyard boutique

Brighton Courtyard boutique
2.0 star property
Brighton City Centre
2.0 out of 10, (1 review)
"This property is in disrepair and is not being maintained. One part of the floor is sinking and propped by loose boards. There is an overall smell of mildew/mold throughout the place, and most of the surfaces need a good cleaning. In the bathroom the shower tap is rigged so that you cannot increase the temperature past a moderate level, and the shower door is falling off the frame. I also came across many spiders. "
United States
Peter
The price is S$256
includes taxes & fees
12 Nov - 13 Nov
Brighton Courtyard boutique
View from property

15. Apartment in Brighton Near the Beach

Apartment in Brighton Near the Beach
2.5 star property
Seafront
The price is S$286
includes taxes & fees
14 Oct - 15 Oct
Apartment in Brighton Near the Beach
A spacious room with wooden floors, a dining table with chairs, and a staircase leading to another level.

16. Dyke Farm Barn | By Huluki Sussex Stays

Dyke Farm Barn | By Huluki Sussex Stays
4.0 star property
Brighton
10.0 out of 10, Exceptional, (1 review)
The price is S$1,192
includes taxes & fees
23 Oct - 24 Oct
Dyke Farm Barn | By Huluki Sussex Stays
A four-poster bed with a brown bedspread, a large window with curtains, a view of greenery, and a bedside table with a lamp.

17. Verdant Rise

Verdant Rise
3.5 star property
Hassocks
The price is S$3,098
includes taxes & fees
5 Nov - 6 Nov
Verdant Rise
A wooden pergola structure with a pool area underneath, featuring stone tiles, lounge chairs, and a table.

18. Heath Retreat

Heath Retreat
3.5 star property
Uckfield
The price is S$1,632
includes taxes & fees
15 Oct - 16 Oct
Heath Retreat
A multi-story building with balconies and a ground-level entrance.

19. Beaches Brighton 1

Beaches Brighton 1
3.5 star property
Seafront
9.4 out of 10, Exceptional, (13 reviews)
"Perfect location, communication amazing, definitely would book again. Place was amazing really great attention to small details which we loved."
United Kingdom
Stewart
Beaches Brighton 1
Property grounds

20. Romantic Lakeview Dome

Romantic Lakeview Dome
2.0 star property
Henfield
The price is S$282
includes taxes & fees
12 Nov - 13 Nov
Romantic Lakeview Dome
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.
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Top Chailey Hotel Reviews

Maldron Hotel Brighton City Centre

Maldron Hotel Brighton City Centre

10/10 Excellent
"Heena on reception was lovely. So was everyone else on reception too. The hotel was really great and not on the main streets.. making it quieter than other places. Great rooms, good vibes, lovely staff. Thank you for a lovely stay. We will be back"
VICTORIA 1-night trip
Posted 2 hours ago
Maldron Hotel Brighton City Centre

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.