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Chester Breaks & Holidays

Chester Coach Holidays

Enjoy a coach holiday visiting the magical city of Chester, with its ancient city walls, stunning landmarks and cultural attractions.

One of the best-preserved walled cities in England, Chester is home to Roman ruins, charming medieval buildings and a fascinating old town. You couldn't choose a better destination for a city break. Walk the city walls, the oldest, longest and most complete in Britain, with parts dating back nearly 2,000 years. Whilst giving you an insight into the history of Chester, the full circuit of the walls also allows you to take in wondrous views of the city.

Things to do on a Short Break in Chester

You’ll be spoilt for choice with the selection of attractions to explore in the city, including the largest Roman Amphitheatre in Britain, cruises along the beautiful River Dee and the 1,000-year-old cathedral with fine examples of medieval wood carvings.

If you enjoy a bit of retail therapy, you’ll love Chester’s Rows in the heart of the city. These unique structures are half-timbered shopping galleries across two tiers, with everything from independent shops, cosy coffee shops and popular restaurants.

What to expect on our Chester Coach Trips?

Our coach holidays visiting Chester include hotel accommodation on a bed & breakfast or dinner, bed & breakfast basis, along with excursions to places of interest. Some of our short breaks also feature evening entertainment and drinks offers!

Our coaches to Chester feature reserved seats and we pick up from a range of local departure points before taking you directly to your holiday destination.

Why book with us

Award-Winning Breaks

The Best Large Travel Company for Coach Holidays & Best Large Company for UK Coach/Touring Holidays

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Book with a low deposit from only £40

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We are unable to access your money until you return from your break

Caledonian reviews

Browse or search holidays visiting Chester below

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Recently Viewed

Chester Christmas Market - Day Break

£26.95

Now £19 .95pp

save £7.00

Duration: 1 Days

From: Darlington, Gateshead, Middlesbrough, Newcastle, Stockton, Sunderland

Coach Seating

Room Types

Departure Points

Return Coach travel with reserved seating.
Day to enjoy the famous City of Walls of Chester and its christmas market.

Departure Date

Tue 9th Dec 25 2025

£26.95 £19.95pp

Tue 9th Dec 25 2025

£24.95 £18.95pp

Tue 9th Dec 25 2025

£24.95 £19.95pp

Tue 16th Dec 25 2025

£26.95 £19.95pp

Tue 16th Dec 25 2025

£26.95 £19.95pp

Tue 16th Dec 25 2025

£23.95 £18.95pp

Book now View Break More Info

Recently Viewed

Cheshire Oaks Designer Outlet

£24.95

Now £14 .95pp

save £10.00

Duration: 1 Days

From: Anlaby, Hull, Wakefield

Coach Seating

Room Types

Departure Points

Modern coach travel with reserved seating
Visit to the Cheshire Oaks Designer Outlet

Departure Date

Tue 9th Dec 25 2025

£24.95 £14.95pp

Tue 9th Dec 25 2025

£24.95 £19.95pp

Tue 16th Dec 25 2025

£23.95 £18.95pp

Thu 25th Jun 26 2026

£26.95 £26.95pp

Thu 16th Jul 26 2026

£27.95 £27.95pp

Thu 13th Aug 26 2026

£27.95 £27.95pp

Thu 3rd Sep 26 2026

£26.95 £26.95pp

Thu 8th Oct 26 2026

£25.95 £25.95pp

Thu 29th Oct 26 2026

£25.95 £25.95pp

Book now View Break More Info

Recently Viewed

Historic Chester & Cheshire Oaks

The Beaufort Park Hotel - Mold

£79.00

Only £79 pp

save -

Duration: 2 Days

From: Darlington, Middlesbrough, Newcastle, Stockton, Sunderland

Coach Seating

Room Types

Departure Points

Modern coach travel with reserved seating
One night dinner, bed and breakfast at The Beaufort Park Hotel - Mold
Visit to Cheshire's county town, Chester to explore its rich history
Visit to the Cheshire Oaks Designer Outlet

Chester - From the best-preserved city walls in England to the Rows: the black and white 700-year-old medieval two-tiered timber-framed galleries that line the main streets - the Cathedral City has a long and rich history.

Cheshire Oaks Designer Outlet - The largest designer outlet in the UK, Cheshire Oaks is a shopping destination of over 140 designer boutiques, with discounts of up to 60%.

The Beaufort Park Hotel, Mold - Stunningly located on the Welsh borders, close to the historic market town of Mold, this splendid hotel offers delightful accommodation, great entertainment, a warm welcome in an ideallocation for our inclusive itinerary.

Departure Date

Sat 3rd Jan 26 2026

£79.00 £79pp

Sat 10th Jan 26 2026

£79.00 £79pp

Sat 10th Jan 26 2026

£79.00 £79pp

Sat 17th Jan 26 2026

£89.00 £89pp

Sat 24th Jan 26 2026

£89.00 £89pp

Sat 31st Jan 26 2026

£99.00 £99pp

Sat 7th Feb 26 2026

£99.00 £99pp

Sat 14th Feb 26 2026

£99.00 £99pp

Sat 21st Feb 26 2026

£99.00 £99pp

Sat 28th Feb 26 2026

£99.00 £99pp

Sat 7th Mar 26 2026

£99.00 £99pp

Sat 14th Mar 26 2026

£99.00 £99pp

Sat 21st Mar 26 2026

£99.00 £99pp

Sat 28th Mar 26 2026

£99.00 £99pp

Sat 11th Apr 26 2026

£119.00 £119pp

Sat 18th Apr 26 2026

£119.00 £119pp

Sat 25th Apr 26 2026

£119.00 £119pp

Sat 16th May 26 2026

£119.00 £119pp

Sat 30th May 26 2026

£119.00 £119pp

Sat 6th Jun 26 2026

£119.00 £119pp

Sat 27th Jun 26 2026

£119.00 £119pp

Sat 25th Jul 26 2026

£119.00 £119pp

Sat 1st Aug 26 2026

£119.00 £119pp

Sat 8th Aug 26 2026

£119.00 £119pp

Sat 15th Aug 26 2026

£119.00 £119pp

Sat 22nd Aug 26 2026

£119.00 £119pp

Sat 22nd Aug 26 2026

£119.00 £119pp

Sat 26th Sep 26 2026

£119.00 £119pp

Sat 10th Oct 26 2026

£119.00 £119pp

Sat 17th Oct 26 2026

£119.00 £119pp

Sat 24th Oct 26 2026

£119.00 £119pp

Sat 24th Oct 26 2026

£119.00 £119pp

Sat 31st Oct 26 2026

£119.00 £119pp

Sat 7th Nov 26 2026

£119.00 £119pp

Sat 7th Nov 26 2026

£119.00 £119pp

Sat 14th Nov 26 2026

£119.00 £119pp

Book now View Break More Info

Recently Viewed

Liverpool & Chester Weekend

£99.00

Only £99 pp

save -

Duration: 2 Days

From: Anlaby, Castleford, Goole, Hessle, Hull, Leeds, Wakefield

Coach Seating

Room Types

Departure Points

Modern coach travel with reserved seating
One night dinner, bed and breakfast at our select hotel
Saturday - An excursion to the lively city of Liverpool
Sunday - visit to Cheshire's county town, Chester to explore its rich history

Departure Date

Sat 24th Jan 26 2026

£99.00 £99pp

Sat 31st Jan 26 2026

£99.00 £99pp

Sat 21st Nov 26 2026

£119.00 £119pp

Sat 5th Dec 26 2026

£119.00 £119pp

Book now View Break More Info

Recently Viewed

Historic Chester & Liverpool Weekend

£99.00

Only £99 pp

save -

Duration: 2 Days

From: Carlisle, Glasgow, Gretna, Hamilton, Paisley

Coach Seating

Room Types

Departure Points

Coach travel with reserved seating
One night dinner, bed and breakfast at our select hotel
Visit to Cheshire's county town, Chester to explore its rich history
An excursion to the lively city of Liverpool

Chester - From the best-preserved city walls in England to the Rows: the black and white 700-year-old medieval two-tiered timber-framed galleries that line the main streets - the Cathedral City has a long and rich history.

Liverpool - It's one of the UK’s most popular city breaks, and it’s clear why. Located right where the River Mersey meets the Irish Sea in the North West of England, it’s bursting with diverse and fascinating history, attractions – and lots and lots of shopping.

Departure Date

Sat 31st Jan 26 2026

£99.00 £99pp

Sat 21st Feb 26 2026

£99.00 £99pp

Sat 21st Mar 26 2026

£99.00 £99pp

Book now View Break More Info

Recently Viewed

2 for 1 Bar

Southport, Liverpool & Lakes Superdeal

The Prince of Wales Hotel - Southport

£169.00

Only £169 pp

save -

Duration: 4 Days

From: Darlington, Gateshead, Middlesbrough, Newcastle, Stockton, Sunderland

Coach Seating

Room Types

Departure Points

Modern coach travel with reserved seating
Three nights dinner, bed and breakfast at The Prince Of Wales Hotel - Southport
2 for 1 Bar Package for three hours each evening with a choice of beers, wines, house spirits & soft drinks.
Free time in Southport
An excursion to Cheshire's county town, Chester to explore its rich history
An excursion to the lively city of Liverpool
A scenic journey on your return through the Lake District, with a visit to Bowness-on-Windermere

Chester - From the best-preserved city walls in England to the Rows: the black and white 700-year-old medieval two-tiered timber-framed galleries which line the main streets of the city – the Cathedral City has a rich history. ‘The Rows’ are now home to an exciting mix of shops, restaurants, pubs, bars, attractions, and experiences.

Liverpool - It's one of the UK’s most popular city breaks, and it’s clear why. Located right where the River Mersey meets the Irish Sea in the North West of England, it’s bursting with diverse and fascinating history, attractions – and lots and lots of shopping.

Bowness-on-Windermere - A busy town right on the shore of the largest lake in The Lake District -and England: Windermere. You’ll find traditional stone cottages, lakefront pubs, B&Bs – and lots and lots of water sports!

Departure Date

Mon 9th Feb 26 2026

£169.00 £169pp

Mon 23rd Feb 26 2026

£169.00 £169pp

Mon 9th Mar 26 2026

£179.00 £179pp

Mon 23rd Mar 26 2026

£179.00 £179pp

Book now View Break More Info

Recently Viewed

Historic Chester & Liverpool Weekend

Holiday Inn - Chester South

£99.00

Only £99 pp

save -

Duration: 2 Days

From: Anlaby, Castleford, Goole, Hessle, Hull, Leeds, Wakefield

Coach Seating

Room Types

Departure Points

Modern coach travel with reserved seating
One night dinner, bed and breakfast at the Holiday Inn - Chester South
Saturday - Visit to Cheshire's county town, Chester to explore its rich history
Sunday - An excursion to the lively city of Liverpool

Chester - From the best-preserved city walls in England to the Rows: the black and white 700-year-old medieval two-tiered timber-framed galleries that line the main streets - the Cathedral City has a long and rich history.

Liverpool - It's one of the UK’s most popular city breaks, and it’s clear why. Located right where the River Mersey meets the Irish Sea in the North West of England, it’s bursting with diverse and fascinating history, attractions – and lots and lots of shopping.

Holiday Inn - Chester South - On the edge of the beautiful Roman City of Chester, you’ll find the Holiday Inn Chester South hotel, offering the perfect blend of modern comfort and warm hospitality, this welcoming hotel provides everything you need for a relaxing stay. Enjoy the on-site Health Club, featuring a heated indoor pool, sauna, steam room, and fully equipped gym.

Departure Date

Sat 14th Feb 26 2026

£99.00 £99pp

Sat 28th Feb 26 2026

£99.00 £99pp

Sat 14th Mar 26 2026

£99.00 £99pp

Sat 28th Mar 26 2026

£99.00 £99pp

Sat 4th Apr 26 2026

£119.00 £119pp

Sat 11th Apr 26 2026

£119.00 £119pp

Sat 18th Apr 26 2026

£119.00 £119pp

Sat 2nd May 26 2026

£119.00 £119pp

Sat 9th May 26 2026

£119.00 £119pp

Sat 16th May 26 2026

£119.00 £119pp

Sat 6th Jun 26 2026

£119.00 £119pp

Sat 13th Jun 26 2026

£119.00 £119pp

Sat 20th Jun 26 2026

£119.00 £119pp

Sat 27th Jun 26 2026

£119.00 £119pp

Sat 4th Jul 26 2026

£119.00 £119pp

Sat 11th Jul 26 2026

£119.00 £119pp

Sat 25th Jul 26 2026

£119.00 £119pp

Sat 1st Aug 26 2026

£119.00 £119pp

Sat 8th Aug 26 2026

£119.00 £119pp

Sat 15th Aug 26 2026

£119.00 £119pp

Sat 22nd Aug 26 2026

£119.00 £119pp

Sat 29th Aug 26 2026

£119.00 £119pp

Sat 5th Sep 26 2026

£119.00 £119pp

Sat 19th Sep 26 2026

£119.00 £119pp

Sat 26th Sep 26 2026

£119.00 £119pp

Sat 3rd Oct 26 2026

£119.00 £119pp

Sat 17th Oct 26 2026

£119.00 £119pp

Sat 31st Oct 26 2026

£119.00 £119pp

Sat 7th Nov 26 2026

£119.00 £119pp

Sat 14th Nov 26 2026

£119.00 £119pp

Book now View Break More Info

Recently Viewed

Historic Chester & Liverpool Weekend

The Crowne Plaza Hotel - Liverpool Airport

£99.00

Only £99 pp

save -

Duration: 2 Days

From: Barnsley, Bradford, Halifax, Huddersfield, Rotherham

Coach Seating

Room Types

Departure Points

Modern coach travel with reserved seating
One night dinner, bed and breakfast at The Crowne Plaza Hotel - Liverpool Airport
Saturday - Visit to Cheshire's county town, Chester to explore its rich history
Sunday - An excursion to the lively city of Liverpool

Chester - From the best-preserved city walls in England to the Rows: the black and white 700-year-old medieval two-tiered timber-framed galleries that line the main streets - the Cathedral City has a long and rich history.

Liverpool - It's one of the UK’s most popular city breaks, and it’s clear why. Located right where the River Mersey meets the Irish Sea in the North West of England, it’s bursting with diverse and fascinating history, attractions – and lots and lots of shopping.

Departure Date

Sat 14th Feb 26 2026

£99.00 £99pp

Sat 14th Mar 26 2026

£99.00 £99pp

Sat 25th Apr 26 2026

£99.00 £99pp

Sat 6th Jun 26 2026

£99.00 £99pp

Sat 18th Jul 26 2026

£99.00 £99pp

Sat 29th Aug 26 2026

£99.00 £99pp

Sat 26th Sep 26 2026

£99.00 £99pp

Sat 24th Oct 26 2026

£99.00 £99pp

Book now View Break More Info

Recently Viewed

2 for 1 Bar

Southport, Liverpool & Lakes Superdeal

The Prince of Wales Hotel - Southport

£169.00

Only £169 pp

save -

Duration: 4 Days

From: Anlaby, Castleford, Goole, Hessle, Hull, Leeds, Wakefield

Coach Seating

Room Types

Departure Points

Modern coach travel with reserved seating
Three nights dinner, bed and breakfast at The Prince Of Wales Hotel, Southport
"2 for 1" bar - for three hours each evening with a choice of beers, wines, spirits and soft drinks
Free time in Southport
An excursion to the lively city of Liverpool
A scenic excursion through the Lake District, with a visit to Bowness-on-Windermere
An excursion to Cheshire's county town, Chester on your return to explore its rich history

Liverpool - It's one of the UK’s most popular city breaks, and it’s clear why. Located right where the River Mersey meets the Irish Sea in the North West of England, it’s bursting with diverse and fascinating history, attractions – and lots and lots of shopping.

Bowness-on-Windermere - A busy town right on the shore of the largest lake in The Lake District -and England: Windermere. You’ll find traditional stone cottages, lakefront pubs, B&Bs – and lots and lots of water sports!

Chester - From the best-preserved city walls in England to the Rows: the black and white 700-year-old medieval two-tiered timber-framed galleries which line the main streets of the city – the Cathedral City has a rich history. ‘The Rows’ are now home to an exciting mix of shops, restaurants, pubs, bars, attractions, and experiences.

The Prince Of Wales Hotel - With its stunning Victorian features, the Prince of Wales Hotel is located in the heart of Southport, within beautifully landscaped gardens. This elegant hotel overlooks Lord Street, the main boulevard in the town and a fantastic shopping area in this seaside resort..

Departure Date

Mon 16th Feb 26 2026

£169.00 £169pp

Mon 16th Mar 26 2026

£179.00 £179pp

Book now View Break More Info

Recently Viewed

Chester - Day Break

£24.95

Only £24 .95pp

save -

Duration: 1 Days

From: Castleford, Hessle, Hull, Leeds, Wakefield

Coach Seating

Room Types

Departure Points

Modern coach travel with reserved seating
Time to explore Cheshire's county town, Chester to explore its rich history

Departure Date

Sat 28th Feb 26 2026

£24.95 £24.95pp

Sat 21st Mar 26 2026

£25.95 £25.95pp

Sat 28th Mar 26 2026

£27.95 £27.95pp

Sat 28th Mar 26 2026

£27.95 £27.95pp

Tue 7th Apr 26 2026

£26.95 £26.95pp

Sat 18th Apr 26 2026

£27.95 £27.95pp

Sat 25th Apr 26 2026

£27.95 £27.95pp

Sat 25th Apr 26 2026

£27.95 £27.95pp

Sat 2nd May 26 2026

£27.95 £27.95pp

Sat 16th May 26 2026

£27.95 £27.95pp

Tue 26th May 26 2026

£27.95 £27.95pp

Sat 30th May 26 2026

£28.95 £28.95pp

Sat 30th May 26 2026

£28.95 £28.95pp

Sat 30th May 26 2026

£27.95 £27.95pp

Sat 30th May 26 2026

£27.95 £27.95pp

Sat 13th Jun 26 2026

£27.95 £27.95pp

Sat 13th Jun 26 2026

£27.95 £27.95pp

Thu 25th Jun 26 2026

£26.95 £26.95pp

Sat 27th Jun 26 2026

£29.95 £29.95pp

Sat 27th Jun 26 2026

£29.95 £29.95pp

Sat 27th Jun 26 2026

£27.95 £27.95pp

Sat 27th Jun 26 2026

£27.95 £27.95pp

Sat 11th Jul 26 2026

£29.95 £29.95pp

Sat 11th Jul 26 2026

£29.95 £29.95pp

Thu 16th Jul 26 2026

£27.95 £27.95pp

Tue 21st Jul 26 2026

£27.95 £27.95pp

Tue 21st Jul 26 2026

£27.95 £27.95pp

Sat 25th Jul 26 2026

£29.95 £29.95pp

Sat 25th Jul 26 2026

£29.95 £29.95pp

Sat 25th Jul 26 2026

£29.95 £29.95pp

Sat 25th Jul 26 2026

£29.95 £29.95pp

Tue 4th Aug 26 2026

£27.95 £27.95pp

Tue 4th Aug 26 2026

£27.95 £27.95pp

Thu 13th Aug 26 2026

£27.95 £27.95pp

Tue 18th Aug 26 2026

£27.95 £27.95pp

Tue 18th Aug 26 2026

£27.95 £27.95pp

Sat 22nd Aug 26 2026

£29.95 £29.95pp

Sat 22nd Aug 26 2026

£29.95 £29.95pp

Sat 22nd Aug 26 2026

£29.95 £29.95pp

Sat 22nd Aug 26 2026

£29.95 £29.95pp

Thu 3rd Sep 26 2026

£26.95 £26.95pp

Sat 12th Sep 26 2026

£28.95 £28.95pp

Sat 12th Sep 26 2026

£28.95 £28.95pp

Sat 19th Sep 26 2026

£29.95 £29.95pp

Sat 19th Sep 26 2026

£29.95 £29.95pp

Sat 26th Sep 26 2026

£27.95 £27.95pp

Sat 26th Sep 26 2026

£27.95 £27.95pp

Thu 8th Oct 26 2026

£25.95 £25.95pp

Sat 17th Oct 26 2026

£27.95 £27.95pp

Sat 17th Oct 26 2026

£27.95 £27.95pp

Sat 24th Oct 26 2026

£26.95 £26.95pp

Thu 29th Oct 26 2026

£25.95 £25.95pp

Sat 7th Nov 26 2026

£26.95 £26.95pp

Book now View Break More Info

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Chester Breaks & Holidays

Chester Coach Holidays

Things to do on a Short Break in Chester

What to expect on our Chester Coach Trips?

Why book with us

Caledonian reviews

Browse or search holidays visiting Chester below

Tour Search

Chester Christmas Market - Day Break

N/A

Cheshire Oaks Designer Outlet

N/A

Historic Chester & Cheshire Oaks

The Beaufort Park Hotel - Mold

Liverpool & Chester Weekend

Mystery Hotel

Historic Chester & Liverpool Weekend

Mystery Hotel

Southport, Liverpool & Lakes Superdeal

The Prince of Wales Hotel - Southport

Historic Chester & Liverpool Weekend

Holiday Inn - Chester South

Historic Chester & Liverpool Weekend

The Crowne Plaza Hotel - Liverpool Airport

Southport, Liverpool & Lakes Superdeal

The Prince of Wales Hotel - Southport

Chester - Day Break

N/A

Exclusive deals and new breaks straight to your inbox!

The Caledonian Claymore - Arrochar

The Caledonian Tower - Blackpool

The Caledonian Torbay - Torquay

The Caledonian New Southlands - Scarborough

Offcanvas

Chester Breaks & Holidays

Chester Coach Holidays

Things to do on a Short Break in Chester

What to expect on our Chester Coach Trips?

Why book with us

Caledonian reviews

Browse or search holidays visiting Chester below

Tour Search

Chester Christmas Market - Day Break

N/A

What's included on your break

Cheshire Oaks Designer Outlet

N/A

What's included on your break

Historic Chester & Cheshire Oaks

The Beaufort Park Hotel - Mold

What's included on your break

Liverpool & Chester Weekend

Mystery Hotel

What's included on your break

Historic Chester & Liverpool Weekend

Mystery Hotel

What's included on your break

Southport, Liverpool & Lakes Superdeal

The Prince of Wales Hotel - Southport

What's included on your break

Historic Chester & Liverpool Weekend

Holiday Inn - Chester South

What's included on your break

Historic Chester & Liverpool Weekend

The Crowne Plaza Hotel - Liverpool Airport

What's included on your break

Southport, Liverpool & Lakes Superdeal

The Prince of Wales Hotel - Southport

What's included on your break

Chester - Day Break

N/A

What's included on your break

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