A stone church with a clock tower, a wooden gazebo, and a stone pathway.

Search Holiday Rentals in Chailey

Q: What are some of the best holiday rentals that Chailey has to offer?

Churchill Country Retreat | By My Getaways : This highly rated holiday home rental in Chailey is equipped with a garden, laundry facilities and WiFi to help you feel comfortable during your stay. It has 6 bedrooms, in addition to a kitchen with a stovetop and a microwave.

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Dates

November 2026

December 2026

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Our top choices for Chailey holiday rentals

A brick wall with a potted plant and flowers.

1. Newstead Farmhouse

Lewes

includes taxes & fees

8 Nov - 9 Nov

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

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

Lewes

Phill

includes taxes & fees

6 Nov - 7 Nov

A rooftop terrace with a view of the city skyline, outdoor seating, and a potted plant arrangement.

3. Q Square by Supercity Aparthotels

Brighton City Centre

Warren

includes taxes & fees

6 Dec - 7 Dec

A cozy lodge entrance with a sign reading 'Duck Lodge,' a small outdoor seating area, and a pathway leading to the entrance.

4. Duck Lodge B&B

Brighton

Meredith

includes taxes & fees

9 Nov - 10 Nov

A hotel room with a bed, bedside tables, a wardrobe, a mirror, and artwork on the walls.

5. Numa Brighton Pavilion

Brighton City Centre

Roshan

includes taxes & fees

6 Dec - 7 Dec

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

Kemptown

Georgina

includes taxes & fees

6 Dec - 7 Dec

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.

7. Osborne Apartments

Eastbourne

Melvyn Spencer

includes taxes & fees

6 Dec - 7 Dec

A bedroom with a bed, two heart-shaped mirrors, and a door.

8. Brighton Abode by Brighton Holiday Lets

Brighton

MWANSA

includes taxes & fees

8 Nov - 9 Nov

A four-poster bed with a brown bedspread, a large window with curtains, a view of greenery, and a bedside table with a lamp.

9. Verdant Rise

Hassocks

10. Apartment in Brighton Near the Beach

Seafront

Daniel

includes taxes & fees

8 Nov - 9 Nov

A historic building with three arched windows and two green doors, numbered 24 and 22.

11. Cliffe Cottage

Lewes

includes taxes & fees

21 Nov - 22 Nov

A multi-level interior with a staircase, a mezzanine with a railing, and a ceiling light fixture.

12. Condo Apartment With Workspace

Haywards Heath

includes taxes & fees

7 Nov - 8 Nov

13. Beautiful & Cosy Apartment in Brighton BN2 3AD

Brighton

"Gorgeous flat, quiet, really comfortable, fantastic set up with everything you need in the kitchen, clean, and even a couple of croissants left for breakfast. The bed was comfy, the room was dark and a blackbird very gently woke us up at a reasonable time in the morning. At the end of the road are loads of decent eateries as well as a lovely pub with excellent bar staff. There's on street parking outside, free overnight to 9am, and then £6.50 for 4 hours. I think you likely have to move...

Sarah

includes taxes & fees

8 Nov - 9 Nov

A modern bedroom with a large bed, a bedside table, a mirror, and a wall-mounted light fixture.

14. Studio In the Lanes

Brighton City Centre

Genevieve

includes taxes & fees

10 Nov - 11 Nov

A bar area with a curved counter, multiple seating options, and a variety of plants and decorations.

15. City Heart Brighton

Brighton City Centre

Stephen

includes taxes & fees

19 Nov - 20 Nov

A multi-story building with balconies and a ground-level entrance.

16. Beaches Brighton 1

Seafront

Stewart

includes taxes & fees

8 Nov - 9 Nov

17. Hangover Hotel

Brighton City Centre

Donald

includes taxes & fees

6 Dec - 7 Dec

A modern living room with a dining area, large windows, and a view of the city.

18. Gorgeous 5 Star Location 2 min to Brighton Beach

Brighton City Centre

includes taxes & fees

8 Nov - 9 Nov

A modern living room with a glass dining table, a sofa, a TV, and a view through a glass door to an outdoor area.

19. Brighton Courtyard boutique

Brighton City Centre

"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. "

Peter

includes taxes & fees

8 Nov - 9 Nov

20. Chalet in Kent With Hot Tub & Countryside Views

Edenbridge

includes taxes & fees

6 Nov - 7 Nov

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Find holiday rentals that suit your style

Top Chailey Hotel Reviews

An arched pathway surrounded by lush green foliage, leading to a central area with string lights and a decorative element.

Trading Boundaries

Uckfield

10/10 Excellent

Brigitte

A spacious lobby with high ceilings, large windows, and modern chandeliers.

East Sussex National

Uckfield

10/10 Excellent

james

A garden pathway with potted plants and sculptures.

Beechwood B&B

Lewes

10/10 Excellent

I chose to stay here for two nights while I was visiting Glyndebourne. Carol and Ceri were so friendly and welcoming. They took such good care of me and made sure that I wanted for nothing. The room I was given was large and extremely comfortable with a private bathroom that overlooked the beautiful garden. Breakfast was always delicious and served in the conservatory. I would definitely recommend a stay here.

Anonymous traveller

A building with a symmetrical facade, a central entrance with a decorative arch, and two illuminated Christmas trees.

Buxted Park Hotel

Uckfield

10/10 Excellent

We arrived and we're greater by the most wonderful Vicky, with whom we hit it off straight away as she up graded us to a suite. It's little things like this which go along way, as the suite was the most opulent, most spacious room I have ever stayed in, it's sweeping viwes to date a lawn Ed tree-lined avenue showing up the splendour of the settings in which this stunning period hotels lies. We were directed to the bar and sampled their food menu. We sat outside opposite the orangery restaurant....

Ralph

A wooden pergola structure with a lattice design, surrounded by lush greenery and flowering plants.

The Wheatsheaf Inn

Haywards Heath

10/10 Excellent

Natalie

The Dorset

Lewes

10/10 Excellent

Noel

A large stone building with multiple windows and a symmetrical facade, surrounded by a well-maintained lawn and trees.

Ashdown Park Hotel & Country Club

Forest Row

10/10 Excellent

Anonymous traveller

A restaurant with green upholstered chairs and tables, a large mural on the wall, and a high ceiling with skylights.

The Grand Brighton

Brighton City Centre

10/10 Excellent

Helen

A cozy room with leather sofas, a wooden table, and a staircase leading to another area.

The Roebuck Hotel by Greene King Inns

Forest Row

10/10 Excellent

Graham

A seaside promenade with a Ferris wheel, beach, and promenade railing.

A Room With A View

Seafront

10/10 Excellent

Spent a fantastic couple of nights at A Room with a View for Valentine's weekend and we were both over the moon with our choice! From the moment you walk in it felt welcoming and cosy, yet had all the mod-cons and more. My husband loved the cooked breakfast (and the coffee machine!) and I felt very spoilt, being gluten free, with all sorts of specialist items for me to enjoy. The room was lovely with an amazing view from the roof terrace. The whole place was clean and very well looked after -...

Charlotte

A modern building with large glass windows and a green-lit interior.

Roffey Park Venue

Horsham

10/10 Excellent

Charlie

A modern hotel entrance with a glass door, a reception desk, and a visible hand sanitizer station.

Staybridge Suites Brighton by IHG

Brighton City Centre

10/10 Excellent

Michelle

A balcony with a white metal chair, a table, and a view of a marina with boats.

Malmaison Brighton

Seafront

10/10 Excellent

The hotel is great. Very clean and has an elevated contemporary feel for the price. Check in was phenomenal with a special shout out to Sam, who was fantastic. We ate in the restaurant and although the food was excellent and the staff really lovely, it was clear that they were very short staffed, as it took ages to order, I waited 30 minutes for my drink, and the food took a very long time to arrive. We ate a starter and main and, were seated for over 2 hours. I asked for the bill as soon as...

Katrina

Sea Spray

Kemptown

10/10 Excellent

Bob

An outdoor dining area with multiple tables and chairs, a bar area with shelves and a television, and large windows providing views of the surroundings.

Holiday Inn London Gatwick - Worth by IHG

Crawley

10/10 Excellent

lisa

Find out more about Chailey

Everything you need to know about Chailey holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chailey holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chailey holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chailey holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chailey. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chailey holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chailey holiday rentals we have selected for you start as low as £29 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chailey rentals

At Expedia, we put the best Chailey holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chailey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chailey holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chailey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

What are some of the best holiday rentals that Chailey has to offer?

Churchill Country Retreat | By My Getaways: This highly rated holiday home rental in Chailey is equipped with a garden, laundry facilities and WiFi to help you feel comfortable during your stay. It has 6 bedrooms, in addition to a kitchen with a stovetop and a microwave.

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.

Search Holiday Rentals in Chailey

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chailey holiday rentals

1. Newstead Farmhouse

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

3. Q Square by Supercity Aparthotels

4. Duck Lodge B&B

5. Numa Brighton Pavilion

6. Upper Rock Brighton Apartments

7. Osborne Apartments

8. Brighton Abode by Brighton Holiday Lets

9. Verdant Rise

10. Apartment in Brighton Near the Beach

11. Cliffe Cottage

12. Condo Apartment With Workspace

13. Beautiful & Cosy Apartment in Brighton BN2 3AD

14. Studio In the Lanes

15. City Heart Brighton

16. Beaches Brighton 1

17. Hangover Hotel

18. Gorgeous 5 Star Location 2 min to Brighton Beach

19. Brighton Courtyard boutique

20. Chalet in Kent With Hot Tub & Countryside Views

Find holiday rentals that suit your style

Top Chailey Hotel Reviews

Trading Boundaries

10/10 Excellent

Find out more about Chailey

Chailey holiday rentals: An excellent choice for every season

How to find incredible deals on Chailey rentals

Frequently Asked Questions

Are there holiday rentals in Chailey?

What are some of the best holiday rentals that Chailey has to offer?

How many holiday rentals are there in Chailey?

What can I see and do in Chailey?

What are holiday rentals like in Chailey?