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Home | Cotswold Way Part Two
Cotswold Way, Bolthole Retreats

The Cotswold Way: Winchcombe to Bath

You’re on the home-from-home straight

The second leg of this Cotswold Way tour takes you from Winchcombe to Bath, the official finish line of the Cotswold Way. Visit Cheltenham, pass Painswick, and discover the lovely little town of Wotton-under-Edge, all while staying in a unique, Cotswold cottage.

During summer you’ll be able to see the grasslands in all their glory; in spring and autumn you can enjoy the beech woodlands; and on those crisp winter days you can see for miles around. Pack your wellies, or pack your sunhat, and enjoy the stunning Cotswold countryside whatever the weather.

From royal Sudeley Castle and Gardens to the royal crescent in Bath

Upon entering Winchcombe, a town renowned for its beauty and Cotswold architecture, you won’t fail to notice the jewel in the town’s crown – Sudeley Castle and Gardens. We are proud to have a portfolio of cottages within the Sudeley Castle Estate, as well as some other lovely properties in the surrounding area. Read on to discover your ideal base for walking the Cotswold Way route.

Barebones Farm in Winchcombe

7 Bedrooms | Sleeps 14

Less than a mile from Winchcombe High Street

Barebones Farm is a large and airy property with character features including exposed beams, stone walls, and an inglenook fireplace. As well as all the space inside, Barebones has a quarter acre of landscaped garden, complete with fruit trees and herbaceous borders. If the weather is a little inclement, you don’t have to miss out on the garden; the property has a conservatory with plenty of cosy seating and underfloor heating. Did I hear someone say ‘walkies?’ Barebones Farm allows two dogs, who are sure to enjoy their stay as much as you do. Lace up your boots and head out along the Cotswold Way with your four-legged friend and return to the reviving surroundings of Barebones Farm.

Kingfisher Cottage in Winchcombe

5 Bedrooms | Sleeps 10

Less than a mile from Winchcombe High Street

Hear the gentle babbling River Isbourne, a tributary of the Avon, as you relax in the lovely enclosed garden at Kingfisher Cottage. Lined with vibrant and pretty flowers, this is the perfect place to sit back with your drink of choice after a day exploring the area. Or, if all the exploring has left you wanting more, how about a spot of on-site fishing? The interior is tastefully furnished, with a neutral palette and pops of colour. There’s even a pool table for you to enjoy.

Mercia House in Winchcombe

4 Bedrooms | Sleeps 8

Less than a mile from Winchcombe High Street

Mercia House is a deceivingly large and modern property in Winchcombe, thanks to a contemporary and spacious extension at the back of the house. There is a large open-plan kitchen, dining, and living area, the perfect space for catching up with friends with drinks and good food. Mercia House is a great example of modern and original features combining to create a beautiful effect. There is a great garden area with seating enough for eight. Like Kingfisher Cottage, the terrace of the property offers wonderful views of Isbourne Valley.

Sudeley Castle Cottages in Winchcombe

Accommodation varies

Sudeley Castle Estate is less than a mile from Winchcombe High Street. The distance will vary slightly between our properties

Each guest cottage at Sudeley Castle estate is unique and inviting. Not only are you situated in the perfect location for the Cotswold Way walking route, you are staying within one of the UK’s most prestigious and picturesque country estates. All the properties here offer something special, but highlights include Castle Gatehouse, which sleeps 4 guests over 2 bedrooms, and is, as the name suggests, the entrance into the estate.

Sudeley Guest Cottage is another great property, which sleeps 6 in 3 bedrooms. Each room is beautifully decorated with antiques, paintings, ornaments, and books, meaning there is almost as much to see inside as there is on the estate and the Castle!

Cyder Press House in The Leigh

4 Bedrooms | Sleeps 8(+2)

10.7 miles from Cleeve Hill and 9.5 miles from Leckhampton Hill

This Grade II listed building is the ideal rambler’s rest. The property, a traditional English farmhouse, is authentic and characterful. It was built in 1667 and its beams, flagstone flooring, and large fireplaces hark back to its long history. Cyder Press House is both family-friendly and dog-friendly, so whether you prefer the company of little ones or furry friends, this is a great property to consider.

A brief circular walk to break up the route

As we carry on moving along the Cotswold Way, we arrive at the Cleeve Hill Ring and the Leckhampton Loop. Close to the vibrant regency town of Cheltenham, we have selected some of our properties nearby. We might be biased, but we think you’ll love them too.

Granary at Hunt Court in Cheltenham

2 Bedrooms | Sleeps 4

12.8 miles from Cleeve Hill and 4.4 miles from Leckhampton Hill

This barn conversion is located on the 25-acre Hunt Court farm and is full of character and charm. The exposed beams and woodburning stove make the Granary a cosy and cosseting space, without feeling stuffy or dark. The barn is decorated to a high standard with modern fixtures and fittings and is in a great location for accessing the local towns and cities, including Cheltenham, Stow-on-the-Wold, Gloucester, and of course – what we are all here for – the Cotswold Way walking route!

Jasmine Cottage in Cheltenham

2 Bedrooms | Sleeps 6

9.8 miles from Cleeve Hill and 5.5 miles from Leckhampton Hill

Jasmine Cottage is a quirky property where guests can expect ‘upside-down living’ and a homely welcome. Jasmine Cottage was originally a stable block and has been tastefully refurbished. There is a log-burning stove and fully equipped kitchen. The open plan nature of the kitchen and living area makes this a great property for catching up with family or friends. Jasmine Cottage is situated next to Amber Cottage (see below), and the two can be booked together for larger parties.

Amber Cottage in Cheltenham

2 Bedrooms | Sleeps 4

9.8 miles from Cleeve Hill and 5.5 miles from Leckhampton Hill

Once again, Amber Cottage is ‘upside-down living’, with bedrooms downstairs and kitchen, dining, and living areas upstairs, accessed via a lovely spiral staircase. Like Jasmine Cottage, this property is a great base from which to explore the Cotswold Way walking route.

Landers in Cheltenham

5 Bedrooms | Sleeps 10

9.8 miles from Cleeve Hill and 3.7 miles from Leckhampton Hill

Landers is an eye-catching property with black and white timber frontage. Inside, there is plenty to catch the eye, too. The property is decorated to a high standard, with great facilities. Enter the garden and you will see why Landers is particularly special. The garden is split into three areas, providing you with the perfect alfresco space, whatever you’re doing. The front garden is the perfect place for a morning cuppa, the huge lawn and garden room at the rear of the property is great for outdoor dining on summer evenings, and finally, the swimming pool is ideal for cooling down after a hot trek along the Cotswold Way.

Old Chapel in Shipton Oliffe

3 Bedrooms | Sleeps 6

6 miles from Cleeve Hill and 7.6 miles from Leckhampton Hill

This 19th century chapel is a perfect example of character and original features combining with modern and cosy decoration. The result is a stunning property which feels like a home-from-home. All of the Old Chapel is stunning, with a wood burning fire and arched windows, but the kitchen is truly special. Complete with vaulted ceiling, original beams, and stained-glass windows, the Old Chapel’s history is most apparent here. There are two lovely outside spaces to enjoy – a courtyard garden with BBQ, and a grassy area with mature trees, small pond, and a bench with lovely views of the Cotswold countryside.

Westerleigh Cottage in Cowley

3 Bedrooms | Sleeps 6

9.6 miles from Cleeve Hill and 3.2 miles from Leckhampton Hill

Westerleigh Cottage is surrounded by greenery, grazing livestock, and woodland. The cottage itself sits near a small grassy knoll, and benefits from a beautiful view of the surrounding area. Westerleigh has a great patio area, with table and chairs and comfy corner seating – so the views and fresh air don’t need to end once you have returned from walking the Cotswold Way route. Inside, the cottage interior is stunning, and, unsurprisingly, has featured in a number of glossy magazines. With such a wonderful place to stay, it could be a challenge to drag yourself away to navigate through the countryside!

Oldbury Barn in Elkstone

4 Bedrooms | Sleeps 8(+3)

11.8 miles from Cleeve Hill and 5.3 miles from Leckhampton Hill

Feel like the VIP that you are in Oldbury Barn, situated behind private gates. The property is decorated to a beautiful standard, resulting in an inviting and welcoming feel within. The barn is perfect for larger walking groups who want a calming and spacious place to recoup. Oldbury Barn is light and airy with a vaulted ceiling, large arched windows and French doors, and a mezzanine floor. The garden is large, with a patio area with outside seating, and a lawn area, perfect for children to enjoy the fresh country air.

Stumble upon the pretty town of Painswick

As we gradually traverse further south on the Cotswold Way route, we come across Painswick, a historic wool town. The settlement is one of the best-preserved in the Cotswolds. As you take in Painswick, you’ll be surrounded by the famous honey-coloured stone buildings. Both our properties in Painswick are shepherd’s huts which have been beautifully decorated. Take a moment (or a little longer!) to enjoy this beautiful little town and immerse yourself in village life.

Tudor Oak at Painswick Lodge in Painswick

1 Bedroom | Sleeps 2

1.5 miles from Painswick

Live the free life of a rover in our Tudor Oak shepherd hut. Spend the day exploring the Cotswold Way walking route and return to your quaint, unique lodging. Soak tired muscles in the wood-fired hot tub, then keep warm and enjoy a glass of bubbly by the firepit as the sun sets. Pretty idyllic, right?

Under the Walnut Tree at Painswick Lodge in Painswick

1 Bedroom | Sleeps 2

1.5 miles from Painswick

Under the Walnut Tree is just as beautiful as Tudor Oak. Instead of the hot tub, you have access to a spring-fed heated swimming pool. With two such lovely places to choose to stay in, we’re glad we aren’t the ones making the decision!

Rest your weary legs at Wotton-under-Edge

Wotton-under-Edge, a charming market town, is worth pushing on for. Home to a pretty high street lined with independent shops and inviting cafes, Wotton is a great place to stay, and you may suddenly want to stay a lot longer than you first thought.

Grindstone Mill in Wotton-under-Edge

6 Bedrooms | Sleeps 12

2 miles from Wotton High Street

Grindstone Mill is as stately on the inside as it is from the outside. A truly impressive property, with a knot garden, large lawn area, and private patio. The Little Avon river runs up to and past the property, with a pretty wooden bridge over. Inside, Grindstone Mill is exquisitely furnished and decorated, with every detail having been thought through. It is a large property, so perfect for big groups or for those who like a little more space.

Finish your route in Bath

Bath is perfectly placed as the endpoint of the Cotswold Way walking route. As a historic spa town famous for its Roman Baths, Bath is a great place for some well-earned rest and relaxation after navigating through the Cotswolds. We have three great properties in the surrounding area, so whether you are looking for a place to stay as you conclude walking the Cotswold Way route, or would like a property well-positioned for Bath and the surrounding walking country, we think these cottages would be ideally suited.

Middle Barn in Dyrham

3 Bedrooms | Sleeps 6

8.6 miles from Bath

Middle Barn and Bull Pen (see below) are both stunning examples of a barn conversion. They are situated within Sands Farm and are separated by a large farm courtyard. This means that the barns are equally as suited to housing separate groups as they are to hosting a larger group over the two properties. Middle Barn is a unique rural holiday home which has retained lots of its original features and character, whilst still feeling modern, fresh, and light. The barn has an outside seating area, perfect for alfresco dining.

Bull Pen in Dyrham

1 Bedroom | Sleeps 2

8.6 miles from Bath

Like Middle Barn, Bull Pen has been lovingly converted into a stunning and intimate property. Guests staying in either barn are invited to take full advantage of the working farm, and can collect fresh eggs from the chickens, go wild swimming, and walk the owner’s dog. We think Bull Pen would be the ideal romantic retreat for couples who want to walk the Cotswold Way, then return to a cosy hideaway, ready to do it all again tomorrow!

Candlemaker’s Cottage in Marshfield

3 Bedrooms | Sleeps 6

8.7 miles from Bath

Candlemaker’s Cottage is a Grade II listed Regency period house. Inside, the cottage is stylish and inviting, with clean but cosy décor. The kitchen has an AGA, making the room a lovely warm and inviting space to dine and drink with friends. If the weather is kind, enjoy a hearty breakfast or brunch on the patio to fuel you for a day of walking and exploring.


Back to part one of the Cotswold Way

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