Overview
A seven day, self-guided walking holiday in the South Cotswolds, following a perfect circuit that starts and ends in the historic and very handsome town of Cheltenham. The Cotswolds are a designated Area of Outstanding Beauty, and you’re never short of outstanding on this holiday, with hill walks that feel untouched by time, and villages and traditional Cotswoldian towns that are packed with ancient sites, and elegant hotels. This is also one of the most fantastic areas of England for fine food, so you can fill your boots at the end of each day. Accessible by train, with luggage transfers.
Full list of our Cotswolds itineraries is available here.
- Sudeley Castle
- Cheltenham
- River Windrush
- Lodge Park
- Sherborne Park Estate
- Painswick
Itinerary
Day 1: Arrive Cheltenham
Arrive in Cheltenham, a spa town celebrated for its Regency architecture, fine shops and restaurants. If time allows, take a stroll through this elegant town or even visit Holst Victorian House, birthplace of composer Gustav Holst.
- Accommodation: The George Hotel or similar in Cheltenham
Day 2: Cheltenham – Winchcombe | 16.8km
Begin the day with an ascent of Cleeve Hill, taking in views of The Cotswold Way before reaching the Neolithic tomb at Belas Knap. Continue on down to Winchcombe, home to Sudeley Castle, which was the final resting place of Katherine Parr, the sixth wife of Henry VIII.
- Walking for the day: 16.8km, ↑445m ↓453m
- Accommodation: The White Hart Inn or similar in Winchcombe
Day 3: Winchcombe – Bourton-on-the-Water | 19.4km
Cross the old Salt Way to descend to the village of Guiting Power, known for its church with a golden Norman doorway. Continue on to Naunton, where one of the landmarks is an ancient dovecote overlooking the River Windrush. Follow the river into Bourton-on-the-Water.
- Walking for the day: 19.4km, ↑348m ↓310m
- Accommodation: Chester House Hotel or similar in Bourton-on-the-Water
Day 4: Bourton-on-the-Water – Northleach | 16.8km
Today’s route weaves around Bourton Lakes, before crossing the hills to Sherborne. Stroll through the grounds of the National Trusts’ Sherborne Park Estate, with its special 18th-century water meadows, and continue on to the historic village of Northleach, famous for its Wool Church. This was funded by local wool merchants during the late medieval period.
- Walking for the day: 16.8km, ↑273m ↓241m
- Accommodation: The Sherborne Arms or similar in Northleach
Day 5: Northleach – Cirencester | 22.7km
Head for Chedworth with its welcoming pub and nearby Roman villa, one of the best-preserved in the country, before continuing on to Cirencester. After London, Cirencester was the second town of Roman Britain. Take the time to stroll around the area with its Corinium Museum and majestic market square overlooked by the huge and recently restored parish church.
- Walking for the day: 22.7km, ↑247m ↓299m
- Accommodation: The Fleece or similar in Cirencester
Day 6: Cirencester – Painswick | 22.3km
A stroll through the 18th-century landscape of Cirencester Park, which is part of the Bathurst Estate, brings you to Sapperton, once a centre for William Morris’ Arts & Crafts movement (payable locally). Follow the old Thames and Severn Canal, before finishing the day walking through perfect rural England to Painswick. Sometimes known as Queen of the Cotswolds, Painswick is noted for St. Mary’s church, which has a churchyard dating back to the 18th century, with 99 yew trees. Another don’t miss is the town’s Rococo Garden.
- Walking for the day: 22.3km, ↑459m ↓428
- Accommodation: St Anne’s B&B or similar in Painswick
Day 7: Painswick – Leckhampton/Cheltenham | 21.5km/33.3km
The Cotswold Way takes you along the Cotswold Edge, passing the Painswick Beacon and Cooper’s Hill, with panoramic views towards Gloucester, the Malvern Hills and Black Mountains in Wales. Explore these distinctive hills, well-known for wildlife and archaeology, before ending the day and your tour back in Cheltenham. Enter Cheltenham through Leckhampton in the south, or continue around the city to enter from Harp Hill in the north, where the circuit began.
- Walking for the day: 21.5km, ↑548m ↓587 or 33.3km, ↑872m ↓899m
- Accommodation: The George Hotel or similar in Cheltenham
Day 8: Departure
Departure after breakfast.
What to expect
Accommodation
Accommodation on this tour includes a mix of mostly small, locally-owned hotels, B&Bs and traditional guesthouses. They have been carefully selected based on a variety of criteria including their location, warm hospitality, fine local food or commitment to responsible tourism. All rooms have en-suite or private bathrooms.
Click to view default hotels
- The George Hotel (Cheltenham)
- The White Hart Inn (Winchcombe)
- Chester House Hotel (Bourton-on-the-Water)
- The Sherborne Arms (Northleach)
- The Fleece (Cirencester)
- St Anne’s B&B (Painswick)
Accommodation is subject to availability. In the event of a particular hotel or guesthouse being fully booked for your chosen dates, we will replace it with a hotel of equal value and quality level. We will provide exact accommodation details to you upon booking confirmation.
Meals
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 and terrain
This tour is rated moderate, with daily distances ranging from 16-23km (33km optional). The terrain is varied, but these are gentle wolds and not mountainous areas (read more about difficulty grades).
The trail follows well-maintained footpaths, bridleways, open fields and some minor roads. The Cotswold Way is a nationally recognised trail and signposted well. 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 mid-March 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.
The weather in the Cotswolds is generally mild throughout the year with temperatures ranging from 10-26C during the spring and summer months. For more information, see our blog, Best time to visit England.
Getting there
Up-to-date travel advice on the United Kingdom is available here (for Canadian citizens) and here (for US citizens).
Click to view travel options
By plane
Our recommended airports for this tour are Birmingham Airport (BHX) or Heathrow (LHR).
By train or bus
- If you are able to travel to Cheltenham without flying, this holiday is reachable by rail with a train station in the town centre. For more details, see Trainline, or use the Omio planner above.
- Cheltenham is served by frequent trains from Birmingham (45mins) and London Paddington (2h). As this is a circular route, you will be walking back to your starting location to depart by the same means you arrived.
UK Visa and entry requirements:
IMPORTANT: From 2025, the UK is implementing a new Electronic Travel Authorisation (ETA) for many countries around the world. Up until 08 January, the ETA requirement only applied to nationals from Bahrain, Jordan, Kuwait, Oman, Qatar, Saudi Arabia and UAE.
On 08 January 2025, the ETA requirement was extended to visitors from eligible non-European countries, including Australian, Canadian and US nationals. Then, on 02 April 2025, the ETA requirement was extended to eligible European countries, referring to most of Europe.
You can view the full list of countries that this applies to here and apply for your ETA here, or on the UK ETA app. The ETA and usually takes up to three working days to be processed, although we advise applying as early as possible, in advance of your travel dates. People travelling with an Irish passport don’t need an ETA.
You can read more about the UK entry requirements on our blog.
Inclusions
Included
- 7 nights accommodation
- 7 breakfasts
- Door-to-door luggage transfers on all walking days (one piece per person, max 20kg)
- Access to your digital pre-departure information (accommodation list, GPS map of the route, baggage transfer information, itineraries, route information of cafes, restaurants, local bus timetables, etc.)
- 24/7 phone assistance by our local office/representative
Excluded
- 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 locally)
- eSIM data for international travel (get an eSIM)
Options, extras and supplements
- If you’re travelling in a group, a supplement applies to group members who would like to have a room of their own
- This holiday is available for solo travellers. However, a supplement will be charged as the cost of rooms and also luggage or private transfers (when applicable) is not shared. Please note that solo travellers are always accommodated in their own room. For logistical reasons, we don’t offer an option for solo travellers to share rooms with other solo travellers
- Extra nights along the trail are bookable upon request
