Chailey Holiday Rentals

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Our top choices for Chailey holiday rentals

Mill Barn by inspirestays.com - a cottage that sleeps 2 guests in 1 bedroom

Mill Barn by inspirestays.com - a cottage that sleeps 2 guests in 1 bedroom
North Chailey
10.0 out of 10, Exceptional, (26 reviews)
"Our second time at Mill Barn and as the first time, everything was perfect, included Penny the host."
United States
yaron P.
The price is AU$1,272
includes taxes & fees
1 June - 2 June
Mill Barn by inspirestays.com - a cottage that sleeps 2 guests in 1 bedroom

Red House Common View

Red House Common View
2.0 star property
Lewes
The price is AU$980
includes taxes & fees
26 May - 27 May
Red House Common View

Churchill Country Retreat | By My Getaways

Churchill Country Retreat | By My Getaways
Lewes
The price is AU$4,700
includes taxes & fees
24 May - 25 May
Churchill Country Retreat | By My Getaways

Bayview Retreat - 3 bedrooms with decking sleeps 6

Bayview Retreat - 3 bedrooms with decking sleeps 6
Pevensey Bay
8.0 out of 10, Very good, (1 review)
"Despite the house being described as "very nice and clean," the presence of white dog hairs on the carpet and sofa was a major disappointment. This issue not only affected the appearance of the house, but also caused practical issues such as getting dog hair on our clothes. As someone with an allergy to dog hair, this made my stay uncomfortable and not as enjoyable as it could have been. As long as I am sure that the hair will be cleaned properly, I would go back with my family the next time."
United Kingdom
Blanka
The price is AU$413
includes taxes & fees
13 May - 14 May
Bayview Retreat - 3 bedrooms with decking sleeps 6

Harbour Hideaway - Free Parking

Harbour Hideaway - Free Parking
Seafront
9.6 out of 10, Exceptional, (5 reviews)
"My teenage son and I had a great time staying at the harbour hideaway. It was easy to access very clean and well equipped. A great location with a lovely view of the harbour. "
United Kingdom
Scott H.
The price is AU$511
includes taxes & fees
14 May - 15 May
Harbour Hideaway - Free Parking

Jellybean - cute and cosy tiny houseboat in a nature reserve by the sea.

Jellybean - cute and cosy tiny houseboat in a nature reserve by the sea.
Shoreham-by-Sea
10.0 out of 10, Exceptional, (1 review)
"Perfect tiny boat, well equipped with everything needed for a comfortable stay. Easy parking close by. Elise is a very helpful & welcoming host, who is happy to suggest things to do locally if needed. Would stay here again! "
United Kingdom
Rachel R.
The price is AU$385
includes taxes & fees
13 May - 14 May
Jellybean - cute and cosy tiny houseboat in a nature reserve by the sea.

Artists Hideaway in Cowfold

Artists Hideaway in Cowfold
3.0 star property
Horsham
The price is AU$267
includes taxes & fees
17 May - 18 May
Artists Hideaway in Cowfold

Cosy Victorian Cottage in Crowborough with Log Burner and parking

Cosy Victorian Cottage in Crowborough with Log Burner and parking
Crowborough
8.6 out of 10, Excellent, (4 reviews)
"Lovely place, will be booking again . "
United Kingdom
Laura
The price is AU$185
includes taxes & fees
18 May - 19 May
Cosy Victorian Cottage in Crowborough with Log Burner and parking

The Heart-of-Brighton Hub / City Center

The Heart-of-Brighton Hub / City Center
Brighton City Centre
The price is AU$234
includes taxes & fees
13 May - 14 May
The Heart-of-Brighton Hub / City Center

Romantic Secret Garden Retreat

Romantic Secret Garden Retreat
Brighton and Hove
10.0 out of 10, Exceptional, (1 review)
The price is AU$353
includes taxes & fees
13 May - 14 May
Romantic Secret Garden Retreat

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)
"Lovely place to stay, hosts very welcoming and helpful "
United Kingdom
Laura
The price is AU$232
includes taxes & fees
17 May - 18 May
Lodge , air con , Free Parking , Mini bar

1 bedroom accommodation in Pevensey Bay, near Eastbourne

1 bedroom accommodation in Pevensey Bay, near Eastbourne
Pevensey Bay, near Eastbourne
10.0 out of 10, Exceptional, (13 reviews)
"We. Had a lovely holiday right near the beach had some lovely walks. The accommodation was very nice and clean. The owner was excellent and very accommodating if we needed anything."
United States
Christine Sheen
The price is AU$473
includes taxes & fees
5 June - 6 June
1 bedroom accommodation in Pevensey Bay, near Eastbourne

The Beach House Peacehaven, Brighton, East Sussex with free parking onsite

The Beach House Peacehaven, Brighton, East Sussex with free parking onsite
Peacehaven
10.0 out of 10, Exceptional, (58 reviews)
"Beautiful property. A real home from home but with a stunning view😁 Had everything you could want. Perfect for trips to seaside towns along the coast. Really lovely host too, thank you"
United Kingdom
RACHEL
The price is AU$200
includes taxes & fees
19 May - 20 May
The Beach House Peacehaven, Brighton, East Sussex with free parking onsite

Studio Annie is the most relaxing place to stay with free off road parking

Studio Annie is the most relaxing place to stay with free off road parking
Worthing
10.0 out of 10, Exceptional, (7 reviews)
"Lovely and cozy, very clean. Perfect for our stay"
United States
Daren W.
The price is AU$230
includes taxes & fees
24 May - 25 May
Studio Annie is the most relaxing place to stay with free off road parking

Bespoke studio with patio, driveway parking, sea, South Downs on the doorstep,

Bespoke studio with patio, driveway parking, sea, South Downs on the doorstep,
Seaford
8.8 out of 10, Excellent, (5 reviews)
"all as expected and very nice place"
United Kingdom
Ratty L.
The price is AU$163
includes taxes & fees
14 May - 15 May
Bespoke studio with patio, driveway parking, sea, South Downs on the doorstep,

Beautiful Rural Barn - stunning interior

Beautiful Rural Barn - stunning interior
Ockley
10.0 out of 10, Exceptional, (16 reviews)
"Its a lovely place, so peaceful & quiet. Very nice interior, all modern"
United Kingdom
Dave Dj Deebs B.
The price is AU$296
includes taxes & fees
26 May - 27 May
Beautiful Rural Barn - stunning interior

Spacious Retreat Private Hot Tub Sea/Downs views/patio 10min walk to Beach/Train

Spacious Retreat Private Hot Tub Sea/Downs views/patio 10min walk to Beach/Train
seaford
9.8 out of 10, Exceptional, (12 reviews)
"What a little gem, host was lovely, and place was even better. Excellent views with total privacy, easy access to other towns and the peace and quiet that we were looking for.Thank you for a lovely short stay Definitely recommend *****"
United Kingdom
Robert C.
The price is AU$444
includes taxes & fees
1 June - 2 June
Spacious Retreat Private Hot Tub Sea/Downs views/patio 10min walk to Beach/Train

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 AU$318
includes taxes & fees
19 May - 20 May
Duck Lodge B&B

The White House Retreat

The White House Retreat
Worthing
9.6 out of 10, Exceptional, (4 reviews)
"Lovely stay, super clean place and super helpful owners. Black book very useful and informative regarding how to use everything and local amenities including buses and taxis. Would definitely recommend, especially the jacuzzi!"
United States
Narea
The price is AU$1,109
includes taxes & fees
13 May - 14 May
The White House Retreat

The White House Studio

The White House Studio
Worthing
10.0 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay but but with a dog we felt it lacked a safe garden area."
United States
Valerie Rose
The price is AU$835
includes taxes & fees
18 May - 19 May
The White House Studio
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

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, 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 favourite 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 depend 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 AU$158 per night. Entering your travel dates in the search wizard might find you 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?

Beautiful Seaside Cottage : This holiday home rental outside of Chailey has laundry facilities and WiFi to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Chailey?

With 6 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 Brighton Beach.

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.