Cotswold Way Short Break

Cotswold Way Short Break

A short walking holiday from Dowdeswell to Kings Stanley, providing a taste of the Cotswold Way.

4 nights
26 miles

From £445 per person

Find out about the tour

About this route

This short break covers the central section of the Cotswold Way from Dowdeswell to King’s Stanley in two walking days. The walk meanders through quiet woodland, open meadows and along the edge of the escarpment, offering fabulous, far-reaching views.

Along with the wonderful scenery, places of note include Crickley Hill Country Park, with its fascinating archaeological site, Painswick and its historic church and the old town of King’s Stanley, where this walk comes to its conclusion.

© Contours Walking Holidays Cotswold Way Short Break map
Dowdeswell/King's Stanley
26 miles (42 km)
19th March to 30th October

Holiday highlights

Wandering through the landscapes of the Cotswolds and enjoying the tranquillity of the English countryside.

Visiting Cooper’s Hill; world-renowned as the site of the annual Cheese Rolling event.

Admiring the white stone buildings and insightful history of the market town of Painswick.

Available tours

CodeTourDurationDifficultyPrice per person
COTWSB From Dowdeswell(T) to King's Stanley 4 nights, 3 days walking Moderate£445

Cotswold Way Short Break 4 nights, 3 days walking

£NNN per person
  • Itinerary
  • What's included?
  • Extra nights?
  • Tour facts
  • Route profile
  • Travel info
  • Weather

Travel to Dowdeswell(T) where your first night's accommodation has been booked

Day 1

Dowdeswell(T) to Birdlip(L). 9.5 miles (15km) / 1621 ft (494 m) ascent

Day 2

Birdlip(L) to Painswick. 7 miles (11.5km) / 781 ft (238 m) ascent

Day 3

Painswick to King's Stanley. 9.5 miles (15.5km) / 1027 ft (313 m) ascent


Depart from King's Stanley after breakfast

Your Itinerary

This itinerary lists our preferred overnight stops for this tour. Sometimes there may be a shortage of available accommodation in a preferred location, in which case we will transfer you from the trail to your accommodation and back again at no extra charge. Overnight stops marked with a (T) will always require transfers as standard.

Overnight stops marked with an (L) have very limited accommodation, and therefore more often than not will also require a transfer, particularly on bank holidays and weekends. We will use non-transfer accommodation wherever possible.

The daily mileages quoted are average trail miles only and do not include the distance from the trail to your accommodation. We do not expect you to have to travel more than a mile from the trail to your accommodation; should your accommodation be further than this, transfers will be provided as standard.

Below are the additional costs that may apply depending on your requirements. Dog-friendly tours are subject to a Daily Dog Charge, which will be listed below if applicable. Our standard prices per person are based upon two people sharing a room; if you are on your own, or are part of a group but require a room of your own, then the Solo Traveller or Single Supplements apply respectively:

A note about transfers
Solo Traveller Supplement
£50.00 per person / per night
Single Supplement
£40.00 per person / per night

You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night
Extra night (Dowdeswell(T))
£70.00 per person / per night

What's included?

  • 4 nights' accommodation in en-suite rooms (where available) in selected B&B’s, hotels, inns and guesthouses along the trail, or a short distance away via taxi provided at our expense.
  • Breakfast each day.
  • Door to door luggage transfer.
  • Maps with the route marked on and a guidebook or route notes describing the trail.
  • An information pack containing an itinerary, instructions on how to find your accommodation each night and a kit list.
  • Detailed travel instructions on how to get to the start of your holiday and back from the end of it.

Extra Nights & Rest Days

The old wool town of Painswick with its ancient stone buildings dating from the 13th century is a good choice for an extra night.

You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night
Extra night (Dowdeswell(T))
£70.00 per person / per night

Tour Facts

Total distance: 26 miles (42 km)
Duration: 4 nights, 3 days walking
Minimum daily distance: 7 miles (11.5 km)
Maximum daily distance: 9.5 miles (15.5 km)
Code: COTWSB Grade: Moderate
Season: 19th March - 30th October
Start of holiday: Dowdeswell(T)
End of holiday: King's Stanley

Route Profile

Cotswold Way Short Break Route Profile

Travel Information

Useful information and travel links that will assist you in your plans to travel to the start of the holiday and back from the end of it are sent to you with your full tour pack. A summary is given below:

By Air - The most convenient major city and international airports are London Heathrow, Bristol and Birmingham.

By Rail - The nearest rail station to the start of the trail (Dowdeswell) is at Cheltenham Spa (about 5 miles away). The nearest rail stations to the end of the trail (Kings Stanley) are either Stonehouse (about 2 miles away) or Stroud (about 4 miles away).

By Bus - There is a bus service from Cheltenham Spa to Dowdeswell, but a taxi would be much quicker. There are bus services from King's Stanley to Stonehouse or Stroud.

From London - Trains run from London Paddington station to Cheltenham Spa. From there a bus/taxi will be required to Dowdeswell.

Return To The Start - The easiest way to return to the start of the trail is to take a taxi from King's Stanley to Dowdeswell.

Weather Information

To find out more about the weather forecast for your chosen holiday's general location, please see the following websites:

  • MetCheck - This website allows you to look up detailed weather information for specific locations as far as six months in advance.
  • Met Office - This website shows regional area forecasts a few days in advance, with a general UK forecast description of up to 30 days in advance.
  • Mountain Forecast - This website shows what the forecast is like up on specific hills and fells, and offers forecasts a few days in advance.

Routes on this trail

Cotswold Way
7 to 14 nights
102 miles
Easy / Moderate+
Dog friendly
From £720 per person
A self-guided walking holiday from Chipping Campden to Bath through the beautiful Cotswolds.Find Out More
Cotswold Way - North Section
4 to 7 nights
47 miles
Easy / Moderate+
Dog friendly
From £435 per person
A pleasant walk from Chipping Campden to Painswick along the Cotswold Way.Find Out More
Cotswold Way - South Section
4 to 8 nights
55 miles
Easy / Moderate+
Dog friendly
From £440 per person
A wonderful walking holiday from Painswick to Bath along the world-famous Cotswold Way.Find Out More

Walking the Cotswold Way with Contours Walking Holidays

Outdoor Journalist Damian Hall takes a walk from Chipping Campden to the Heritage Listed City of Bath, along one of the most quintessentially English trails in the country.
Watch Now