Chestfield Holidays from £431

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Your Chestfield Holiday

The best way to experience this lively city is with a custom-made Chestfield holiday package. Base yourself in the neighbourhood of Birchington, which is good for nature, history and walking or choose someplace else — our packages are all about you. Every trip to Chestfield needs a well-thought-out itinerary. Fill yours with major attractions such as Whitstable Harbour, Whitstable Beach and Tankerton Beach. Browse Expedia's wide range of travel options and start organising your ultimate holiday to Chestfield now.

Top Chestfield Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
4 Landgate Cottage Winchelsea

4 Landgate Cottage Winchelsea

3.5 out of 5
Price was £1,039, price is now £431 per person
£431
per person
24 Oct - 30 Oct
found 11 hours ago
Return flight included
Glasgow (GLA) to London (LGW)
9/10 Wonderful! (2 reviews)
Les Dunes

Les Dunes

3.5 out of 5
Price was £1,827, price is now £567 per person
£567
per person
24 Oct - 30 Oct
found 11 hours ago
Return flight included
Glasgow (GLA) to London (LGW)
No reviews
Maytham Cottage

Maytham Cottage

4 out of 5
Price was £2,266, price is now £888 per person
£888
per person
24 Oct - 30 Oct
found 11 hours ago
Return flight included
Glasgow (GLA) to London (LGW)
No reviews
Whitefriars

Whitefriars

4 out of 5
Price was £2,395, price is now £982 per person
£982
per person
24 Oct - 30 Oct
found 11 hours ago
Return flight included
Glasgow (GLA) to London (LGW)
No reviews
Corkwood

Corkwood

3 out of 5
Price was £2,134, price is now £879 per person
£879
per person
24 Oct - 30 Oct
found 11 hours ago
Return flight included
Glasgow (GLA) to London (LGW)
No reviews

Chestfield Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Southend Airport (SEN)
Max Temp Winter
7ºC
Max Temp Summer
18ºC
Top Sights
Whitstable Beach, Tankerton Beach and Whitstable Castle and Gardens

Top hotels in Chestfield

Ashford International Hotel & Spa

Ashford International Hotel & Spa

4 out of 5
Simone Weil Avenue, Ashford, England
Fully refundableReserve now, pay when you stay
The price is £70 per night from 21 Sept to 22 Sept
£70
21 Sept - 22 Sept
includes taxes & fees
7.8/10 Good! (1,002 reviews)
lovely hotel
"We enjoyed our one night stay at this hotel. Room and hotel were very clean and comfortable. We got there late at night and had to leave early in the morning, so didn't get to use any of their amenities, but breakfast was good (with good options) and room fridge was stocked with beer! Check in and ..."

Reviewed on 19 Aug 2025

Ashford International Hotel & Spa
The Falstaff Hotel

The Falstaff Hotel

3 out of 5
8-10 St Dunstan Street Kent, Canterbury, England
Fully refundableReserve now, pay when you stay
The price is £107 per night from 21 Sept to 22 Sept
£107
21 Sept - 22 Sept
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Parking
"All good apart from the parking arrangements with a third party,had great difficulty with registration on line or over phone so had to get reception to sort it out very stressful.Why do you have to have a third party to manage your car park?"

Reviewed on 20 Aug 2025

The Falstaff Hotel
ABode Canterbury

ABode Canterbury

4 out of 5
30-33 High St, Canterbury, England
Fully refundableReserve now, pay when you stay
The price is £69 per night from 22 Sept to 23 Sept
£69
22 Sept - 23 Sept
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
Great central location
"The staff were great and friendly. They were helpful with recommendations and the location was amazing. We found free parking a 15 minute walk away and left the car there for 3 days while we explored the town"

Reviewed on 23 Aug 2025

ABode Canterbury
See all 2,112 properties in Chestfield
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.

The Advantages of Chestfield Weekend Breaks

Discover a different side of the British Isles with a weekend break in Chestfield. Take short breaks away from home and enjoy some quality time in a beautiful place. You’ll come back feeling refreshed and inspired. You can have an action-packed Chestfield weekend break or get some peace with a relaxing holiday. Whatever experience you’re looking for, find it with our deals on hotels in Chestfield.

Cheap Weekend Breaks to Chestfield

There are lots of ways to take cheap weekend breaks to Chestfield. Expedia offers deals on car hires and hotel rooms and covers trips for all kinds of travellers. The best way to save is with our holiday packages in Chestfield. First, choose your car hire and hotel reservation. Then we’ll bundle them together into one discounted price. Solo explorers, couples, families, and groups of friends can discover budget solutions for their weekend breaks. Once you arrive, enjoy some of the fun things to do, many of which are free or cheap to experience  

Chestfield Romantic Weekend Breaks

Couples love taking romantic weekend breaks in Chestfield. Whisking your lover away for a romantic Chestfield weekend break is the perfect opportunity to make new memories together. Expedia offers all kinds of hotel options, so you can find romantic hotels in Chestfield and choose the best place for you. Check out our deals on beautiful properties, and you’ll save even more when you choose to package your hotel reservation with a car hire.

Family Weekend Breaks in Chestfield

Set some time aside to experience family weekend breaks in Chestfield. There are plenty of excellent family-friendly hotels in Chestfield within our selection of hotels. You can also find a place to call home in one of the holiday rentals in Chestfield. With accommodation, activities, and adventure all waiting, there’s never been a better time to plan Chestfield family weekend breaks.

All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Whitstable Beach as well as a small group of people

Whitstable Beach

Pack a picnic and your swimsuit for a day out on this attractive shingle beach lined with rows of pastel-colored wooden huts.

Whitstable Beach
Whitstable Harbour which includes a marina and industrial elements

Whitstable Harbour

Watch fishing boats sail in with their catches and savor oysters and other fruits of the sea at this busy working harbor.

Whitstable Harbour
Tankerton Beach

Tankerton Beach

If a restful holiday is part of your travel plans, Tankerton Beach might be the perfect place to visit during your trip to Whitstable. While you're in the area, stroll along the seaside.

Tankerton Beach

What to do in Chestfield

Leeds Castle, Canterbury & Dover Tour with Admission

Leeds Castle, Canterbury & Dover Guided Tour from London

£105
per adult
88% of travellers recommend
Leeds Castle, Canterbury & Dover Guided Tour from London
Canterbury: Walking Tour with Green Badge Guide

Canterbury: Walking Tour with Green Badge Guide

£15
per adult
94% of travellers recommend
Canterbury: Walking Tour with Green Badge Guide
Kent Garden of England in Private Vehicle Tour including Passes

Private Tour of Kent Garden of England including Passes

£1,030
per adult
Private Tour of Kent Garden of England including Passes
See all activities in Chestfield

Frequently asked questions

Why should I book my Chestfield holiday with Expedia?
Expedia has your back for every detail of your Chestfield getaway. You'll always get the best prices, but when you bundle your hotel, flights and/or hire car into a holiday package, you'll score even bigger savings. Keen to truly make the most of your adventure? Add some activities and tours to your customised package. Expedia offers flexible cancellation policies on most bookings, so you won't need to worry if your travel plans change. Visit our Customer Service Portal link to learn more.
When is the best time of year to holiday in Chestfield?
Chestfield gets busy in January, April and November. If you're not a fan of large crowds and prefer a calmer pace, lock in your trip for June, October and December. Organise your trip to Chestfield according to what type of holiday you want. January is the coolest month, when daytime temperatures average 5ºC. In July, the warmest period, you'll experience averages of 17ºC during the day.
How do I get a cheap holiday to Chestfield?
Search for flights that fit in with your schedule, add a hotel to your booking and watch the savings grow with a Chestfield holiday. It's as easy as that! From hotels and flights to hire cars and tours, Expedia makes travelling on a budget easy. And with more than 400 airlines and 321,000 hotel options throughout the world to select from, you won't be short of choice. Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Chestfield holiday?
Make sure your next holiday in Chestfield is an unforgettable one by stopping by its most popular attractions. Whitstable Beach, Whitstable Harbour, Tankerton Beach and Whitstable Castle and Gardens are some of the things worth seeing while you're here.
What is the best area to stay in when on holiday in Chestfield?
An escape to Chestfield isn't complete without visiting Chestfield Golf Club. Why not book a stay near this much-loved attraction?
Do I need a visa for my Chestfield holiday?
Visa requirements for Chestfield vary depending on your nationality and the purpose of your visit. We recommend checking official government websites to determine if you need a visa for your trip. Here you'll also find the most up-to-date information, including details about application procedures or any supporting documentation that might be necessary. Enquire about your visa requirements in advance to ensure a hassle-free travel experience. Finally, double-check to see that your passport has at least six months validity from your date of return.
What should I wear on my Chestfield holiday?
Think about the types of things you'll be doing during your Chestfield trip and travel with pieces that you can mix and match. For fashion inspiration or even information on dress codes, browse style blogs or social media accounts.
What does an Expedia Chestfield holiday include?
That mostly depends on you. Simply choose from a range of Chestfield bundles, such as a flight, hotel and hire car. You can also book a flight and a hotel, or a flight and a car hire. Once you've made your booking, add the fun stuff like activities and experiences. Whatever your Chestfield break looks like, you'll save! Expedia features all types of properties, with the most preferred in Chestfield being cottages. Whatever style of retreat you're looking for, Expedia gives you the flexibility and freedom to personalise your holiday.
Does Expedia offer Book Now, Pay Later Chestfield holidays?
Your bank balance shouldn't get in the way of escaping on holiday, so Expedia has devised a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book your dream getaway without drying up your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's convenient payment plans. If making bite-sized repayments each month sounds right for you, choose this option during the checkout process.
  • No-deposit holidays: Pressing the "book now" button is much easier with this option. With no upfront fee for your escape, you can Book Now, Pay Later and start working on your travel plans.

Can I choose my airline with a Chestfield Expedia holiday?
Yes — and it's simple too. Expedia has access to more than 400 partner airlines all over the world. Our holiday packages give you the freedom to pick from available flight, hotel or activity options that fit your needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.