Chailey Vacation Rentals from CA $55: Short-Term Rentals for 2026

Q: What's the top vacation rental that Chailey has to offer?

Churchill Country Retreat | By My Getaways : Visitors like this Chailey vacation home rental. It 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chailey vacation rentals

A bathroom with a bathtub, a wooden shelf with toiletries, and a view into the bedroom.

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

North Chailey

"My husband and I enjoyed a week in Mill Barn in early June. Unfortunately the weather didn't want to play along so we couldn't enjoy the beautiful garden as much as I had hoped, but that was no loss - the cottage is adorable inside too and it's perfect for cozy cocooning when it's rainy. We enjoyed the smart TV, bath and wonderful shower, as well as the well equipped kitchen. There are plenty of fun day trips in the area and Penny was incredibly kind and helpful during our stay. I would book...

Anonymous traveller

CA $1,104 total

includes taxes & fees

Nov 2 - Nov 3

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

CA $151 total

includes taxes & fees

Oct 20 - Oct 21

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

3. Duck Lodge B&B

Brighton

Meredith

CA $290 total

includes taxes & fees

Nov 9 - Nov 10

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

4. Q Square by Supercity Aparthotels

Brighton City Centre

Warren

CA $170 total

includes taxes & fees

Nov 15 - Nov 16

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

CA $137 total

includes taxes & fees

Nov 8 - Nov 9

A narrow hallway with a bed in the background, a mirror on the left, and a door on the right.

6. Pet friendly and central Laines location, 1 minute from station

Brighton City Centre

Monica L.

CA $199 total

includes taxes & fees

Oct 20 - Oct 21

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

Kemptown

Alan

CA $184 total

includes taxes & fees

Nov 10 - Nov 11

A rocky beach with a cliff and wooden posts in the water.

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

Seaford

Gazelle J.

CA $160 total

includes taxes & fees

Oct 20 - Oct 21

A room with a wooden table, a bench with floral cushions, and a view through large windows.

9. Stylish Lewes Apartment - Gorgeous Views

Lewes

Colin B.

CA $379 total

includes taxes & fees

Nov 11 - Nov 12

A dining area with tables and chairs, large windows with blinds, and a view of the sea.

10. Majestic Hotel Eastbourne by Belvilla - Twin Room with Sea View

Eastbourne City Centre

Catherine

CA $55 total

includes taxes & fees

Oct 20 - Oct 21

A spacious living room with a wooden dining table, a sofa set, a TV, and a staircase leading to another level.

11. Beacon Cottage by inspirestays.com - a cottage that sleeps 2 guests in 1 bedroom

Ditchling

Anonymous traveller

CA $1,163 total

includes taxes & fees

Nov 9 - Nov 10

A wooden exterior with a pergola, a small potted plant, and a grey sofa.

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

Hove

Sally

CA $235 total

includes taxes & fees

Oct 23 - Oct 24

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

13. City Heart Brighton

Brighton City Centre

Stephen

CA $169 total

includes taxes & fees

Nov 2 - Nov 3

A dimly lit room with a bed, a desk with a lamp, and a wicker chest of drawers.

14. Brighton Oasis of Calm seconds from the seafront and beach with an EnSuite Room

Hove, Brighton

Catherine

CA $160 total

includes taxes & fees

Oct 27 - Oct 28

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

15. Studio In the Lanes

Brighton City Centre

Genevieve

CA $177 total

includes taxes & fees

Nov 8 - Nov 9

16. The Heart-of-Brighton Hub / City Center

Brighton City Centre

anna k.

CA $251 total

includes taxes & fees

Oct 21 - Oct 22

A hot tub with a wooden deck, surrounded by lush greenery and hanging pink flowers.

17. Romantic Secret Garden Retreat

Brighton and Hove

Kai M.

CA $313 total

includes taxes & fees

Oct 20 - Oct 21

A view from a room with a large window overlooking a beach and the sea.

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

Peacehaven

Thomas Sebastian P.

CA $242 total

includes taxes & fees

Oct 21 - Oct 22

19. Orchard View Shepherds Hut

Henfield

CA $233 total

includes taxes & fees

Oct 20 - Oct 21

A rustic interior with exposed wooden beams, stone steps, and a cozy seating area.

20. Bellflower Cottage - Ashdown Forest

Haywards Heath

Phyllis M.

CA $1,749 total

includes taxes & fees

Nov 5 - Nov 6

View all properties

Find vacation rentals that suit your style

Apartments

Aparthotels

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

Sandman Signature London Gatwick Hotel

10/10 Excellent

"I have stayed at the hotel many times. The lady who checked me in was very quick and very friendly. The hotel is very clean and parking is very easy. It’s one of my favourite hotels with gym and swimming even it’s not very big but I have never seen it being very busy."

Hampton by Hilton London Gatwick Airport

8/10 Good

"Literally inside the airport! Can’t get closer than that so it’s very convenient, especially if flying from easyJet where the check-in deals are just by the entrance to the hotel. Bathroom was very small, bed and pillows were really comfortable. I didn’t have time for breakfast. There was a lot of noise from trolleys and floors above, not very sound proof."

The Burlington Hotel

8/10 Good

"The hotel was so in need of a little tlc. The room, superior twin was fine, recently refurbished, clean and comfy bed. Bathroom needed updating, but ok.The real issue was no means of fresh air, as windows were fixed shut and no other means of ventilation. The lift was appalling. Parking was ok and easily accessible. Outside painting of front especially entrance area would be a wise investment."

Find out more about Chailey

Everything you need to know about Chailey vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chailey vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chailey vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chailey vacation rentals we have selected for you start as low as CA $55 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 vacation 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 vacation.

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 vacation rentals in Chailey?

Yes, we offer vacation rentals in Chailey near Bluebell Railway - Sheffield Park Station, or you can select a more remote option if you want a relaxing stay.

What's the top vacation rental that Chailey has to offer?

Churchill Country Retreat | By My Getaways: Visitors like this Chailey vacation home rental. It 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 vacation rentals are there in Chailey?

With 7 Expedia vacation rentals, you're sure 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 larger area, you’ll find Bluebell Railway - Sheffield Park Station and Sheffield Park Garden.

What are vacation rentals like in Chailey?

Vacation rentals are privately owned accommodations you can book for a short or long stay in Chailey. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family trip or a small group gathering.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chailey vacation rentals

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

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

3. Duck Lodge B&B

4. Q Square by Supercity Aparthotels

5. Numa Brighton Pavilion

6. Pet friendly and central Laines location, 1 minute from station

7. Upper Rock Brighton Apartments

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

9. Stylish Lewes Apartment - Gorgeous Views

10. Majestic Hotel Eastbourne by Belvilla - Twin Room with Sea View

11. Beacon Cottage by inspirestays.com - a cottage that sleeps 2 guests in 1 bedroom

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

13. City Heart Brighton

14. Brighton Oasis of Calm seconds from the seafront and beach with an EnSuite Room

15. Studio In the Lanes

16. The Heart-of-Brighton Hub / City Center

17. Romantic Secret Garden Retreat

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

19. Orchard View Shepherds Hut

20. Bellflower Cottage - Ashdown Forest

Find vacation rentals that suit your style

Top Chailey Hotel Reviews

Sandman Signature London Gatwick Hotel

Hampton by Hilton London Gatwick Airport

Sofitel London Gatwick

Maldron Hotel Brighton City Centre

Hilton London Gatwick Airport

The Burlington Hotel

West Beach Hotel Brighton

Leonardo Royal Hotel Brighton Waterfront

DoubleTree by Hilton Brighton Metropole

Find out more about Chailey

Frequently asked questions

Go further with the Expedia app