This superb inn-to-inn South Cotswold Ring self-guided walking holiday will take you through the southern part of the Cotswolds and will let you enjoy some of the best walking the Cotswolds have to offer. The circuit starts and finishes in Cheltenham and takes in the most picturesque towns and villages of the Cotswolds. We arrange comfortable accommodation in en-suite rooms at hotels and accredited guesthouses on this itinerary, and we transfer your luggage between each of the accommodations.
Full list of our Cotswolds itineraries is available here.
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Day 1: Arrive Cheltenham
Arrive in Cheltenham – a beautiful spa town celebrated for its Regency architecture and fine shops and restaurants.
- Accommodation: Beaumont House or similar
Day 2: Cheltenham to Winchcombe | 11 km / 7 mi
Walk over Cleeve Hill to pass the Neolithic tomb at Belas Knap and then down to Winchcombe, home to Sudeley Castle.
- Walking for the day: 7 miles / 11 km, 3-4 hours
- Accommodation: White Heart Inn or similar
Day 3: Winchcombe to Bourton-on-the-Water | 21 km / 13 mi
Cross the old Salt Way to descend to the beautiful villages of Guiting Power (a church with gorgeous golden Norman doorway) and Naunton, with its ancient dovecote overlooking the River Windrush, which you then follow into Bourton-on-the-Water.
- Walking for the day: 13 miles / 21 km, 5-6 hours
- Accommodation: Chester House Hotel or similar
Day 4: Bourton-on-the-Water to Northleach | 17 km / 11 mi
The route weaves around Bourton lakes, then crosses the hills to Sherborne. Stroll through the landscaped Sherborne Park and continue to the tranquil and historic village of Northleach, with its glorious wool church, mechanical music museum and air of timelessness.
- Walking for the day: 11 miles / 17 km, 4-5 hours
- Accommodation in Northleach
Day 5: Northleach to Cirencester | 22 km / 14 mi
Head for Chedworth with its welcoming pub (and a nearby Roman villa, one of the best-preserved in the country), before continuing to Cirencester, after London the second town of Roman Britain, with its excellent Corinium Museum and its majestic market square overlooked by the huge and recently restored parish church.
- Walking for the day: 14 miles / 22 km, 5-6 hours
- Accommodation in Cirencester
Day 6: Cirencester to Painswick | 21 km / 13.5 mi
A stroll through the 18th-century landscape of Cirencester Park brings you to Sapperton, once a centre for William Morris’s Arts & Crafts Movement. Follow the old Thames & Severn Canal, and then walk through perfect rural England to Painswick, ‘Queen of the Cotswolds’, noted for its fascinating churchyard and the Rococo Garden.
- Walking for the day: 13.5 miles / 21 km, 5-6 hours
- Accommodation: St Anne’s B&B or similar
Day 7: Painswick to Cheltenham | 20 km / 13 mi
Walk through the countryside immortalised in Laurie Lee’s ‘Cider with Rosie’ to Sheepscombe (which is featured in the book), which straddles an enchanting valley. The Cotswold Way takes you along the Cotswold Edge, with panoramic views towards Gloucester, the Malvern Hills and the Black Mountains in Wales.
- Walking for the day: 13 miles / 20 km, 5-6 hours
- Accommodation: Beaumont House or similar
Day 8: Departure
Departure or extra nights upon request.
What to Expect
Accommodations on this tour include a mix of charming small hotels, B&Bs and guesthouses. They have been carefully selected for their location, atmosphere, cuisine and/or unique services. All rooms have en-suite or private bathrooms.
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*Hotels are subject to availability. In case a particular hotel is fully booked for your desired dates, we will replace it with a hotel of equal or higher value and quality level. We will provide exact accommodation details to you upon booking confirmation.
Breakfast is included on all days. When no restaurant location is available on the route, lunches and snacks should either be bought from local shops, or packed lunch can be pre-ordered from your hotel the night before. You can have dinner at the guesthouse you are staying at or at the village pubs and restaurants.
Difficulty & terrain
This itinerary allows you to walk at a leisurely pace, giving you time to explore this fascinating area of outstanding natural beauty. Most days offer 4-6 hours of walking. You will cover a variety of terrain, but these are gentle wolds and not mountainous areas. Ascents and descents are usually 150-200 m per day (read more about difficulty grades). The trail follows well-maintained footpaths, bridleways, open fields and some minor roads. The route is not specially designated and waymarked, so check carefully against your guidebook. Generally, the route is easy to navigate, and we will provide you with detailed road notes and maps, and you can call our 24/7 local assistance phone number anytime. More detailed info on route navigation will be included in your holiday information pack.
When to go
This trip is available from the mid-April until mid-October. The flexibility of self-guided holidays means that there are no fixed dates and you can start your trip on any date during the season. If you are a seasoned and well-equipped hiker, we can eventually book you on off-season dates.
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By train or bus
- Cheltenham is served by frequent trains, with some direct trains to London (Paddington), Birmingham, and Bristol. As this is a circular route, you will be walking back to your starting location to depart by the same means you arrived.
- For more information, use the Omio planner above.
- 7 nights in a twin or double rooms with an en-suite or private bathroom (3-star hotels, B&Bs and guesthouses)
- 7 breakfasts
- Detailed journey documentation and practical information: personalised trip notes and maps (emailed before departure and a hard copy provided at the first hotel; one set per booking)
- Luggage transfers from hotel to hotel – up to 15 kg per person
- 24/7 phone assistance by our local office/representative in Cheltenham
- Airfare and connecting land transfers
- Lunches, dinners, drinks and snacks
- Travel insurance (required – get a quote online)
- Personal expenses
- Local tourist taxes and entry fees (payable on-site)
- Any items not explicitly listed as included
Options, extras & supplements
- A supplement applies to members of a group who require a single room
- This holiday is available for solo travellers; a supplement will be charged as accommodation and luggage transfer costs are not shared (we never mix and match – solo travellers will be accommodated in single rooms)
- Extra nights along the trail are bookable upon request