Self Catering Holiday Cottages in Cheltenham

Stepping Stones is a spacious, pet-friendly holiday cottage in Bourton-on-the-Water, perfect for families or small groups. Set beside the River Windrush, it sleeps five across three bedrooms, with space for two more on a sofa bed. The cottage features a private riverside patio, a well-equipped kitchen, an open-plan living area, a family bathroom and a downstairs WC. Shops, tearooms, pubs and attractions like Birdland and the Model Village are just a short walk away. Stepping Stones offers a fantastic base for exploring the Cotswolds with children, friends or dogs in tow with free WiFi, parking and everything needed for a relaxed self-catering stay.

Kestrel Cottage is a spacious, pet-free holiday rental in the heart of Bourton-on-the-Water, perfect for couples seeking a peaceful Cotswolds escape. Located on the first floor of a converted water mill, it features a double bedroom, sofa bed, modern bathroom, and an open-plan kitchen, dining and living area. With beautiful Cotswold stone walls and village views, it offers comfort and charm in equal measure. Shops, cafés, pubs, and local attractions are all within walking distance. With free WiFi, parking, and everything needed for a relaxed self-catering break, Kestrel Cottage is an ideal base for exploring the Cotswolds year-round.

Skylark Cottage is a pet-free holiday home in Bourton-on-the-Water, ideal for couples or small families. Set across two floors in a converted Cotswold stone watermill beside the River Windrush, it includes a cosy attic bedroom with en-suite, a bright living area with sofa bed, and a well-equipped kitchen for self-catering stays. Guests can walk to local pubs, tea rooms, shops and attractions, all just moments from the door. Free WiFi and private parking are included. With scenic footpaths and charming villages nearby, Skylark Cottage is a comfortable base for exploring the beauty and heritage of the Cotswolds.

Swallow Cottage is a welcoming base that feels like home. A charming and pet-friendly hideaway for two, the holiday cottage is tucked away near the centre of Bourton-on-the-Water, one of the Cotswolds' prettiest villages. The one-bedroom bolthole is ideal for couples looking to unwind and enjoy time together. A sofa bed in the living room provides accommodation for one or two extra guests, so it is also an excellent choice for a small family to use as they explore Cotswold towns and countryside. Swallow Cottage is one of four self-catering rentals in a beautifully restored former mill. It features ground-floor accommodation with original stone walls and oak beams all within a few steps of Bourton-on-the-Water's independent tea rooms, shops, pubs and local sights. 

This romantic one-bedroom retreat offers tranquil riverside views and is just moments from tea rooms, shops, and popular attractions like Birdland and the Model Village. Ideal for dog-friendly getaways, Robin Cottage sleeps two, with a sofa bed for extra guests, so it is perfect for couples or small families. Enjoy scenic walks to Lower and Upper Slaughter, and explore local trails and cycle routes. Robin Cottage is the ideal choice of holiday home for a relaxing, self-catering Cotswold escape all year round and a peaceful base to explore one of England’s prettiest villages.

Easter House is a beautiful Cotswold stone double-fronted house in Winchcombe, sleeping ten across five bedrooms with four en-suites. Recently refurbished, the group holiday home combines period character with contemporary styling, blending golden-honey stone walls, original features, and modern comforts inside and out. The open-plan living area flows onto a two-level enclosed garden, while the fully equipped kitchen handles family feasts easily. Sudeley Castle sits nearby, Cleeve Hill walks start from the door, and Winchcombe's restaurants and pubs are steps away. This self-catering accommodation puts Broadway, Cheltenham, and the Cotswolds' prettiest villages within easy reach.

Beautifully presented, this welcoming holiday retreat for two provides a cosy self-catering base from which to explore the Cotswolds and its many attractions. Popular with walkers, cyclists and garden enthusiasts, there are also lots of houses and gardens to visit locally. There are good pubs and of course plenty of tea rooms! The village pub in Kineton serves excellent food and just a few minutes walk away. Tourist board rating: 4 Star

"Bears Court Barn 2" is a 3 bed holiday Cottage sleeping up to 6 guests in Gloucestershire. Located in the Cotswold Area of Outstanding Natural Beauty, the historic village of Bourton-on-the-Water dates back to Neolithic times with over 100 buildings being Grade II listed or higher. The picturesque high street nestles alongside the...

"1 Bed Cottage in Upper Coberley" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. Additional information and rulesNo dogs allowed - 1 bedroom – double - 1 bathroom - Electric oven and hob, fridge/freezer, dishwasher and washer/dryer - Electric and central heating and towels included - Off-road parking for 1...

"Flagstone Cottage" is a 1 bed holiday Apartment sleeping up to 2 guests in Gloucestershire. Stow-on-the-Wold, the highest village in the Cotswolds and the site of an Iron Age fort, epitomises olde worlde England. Since the 12th century, this historic market town has hosted numerous fairs, including a biannual Gypsy Horse Fair, craft...

"Bears Court The Annex" is a 2 bed holiday Cottage sleeping up to 4 guests in Gloucestershire. Located in the Cotswold Area of Outstanding Natural Beauty, the historic village of Bourton-on-the-Water dates back to Neolithic times with over 100 buildings being Grade II listed or higher. The picturesque high street nestles alongside the...

"Swallow Studio" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. The bustling village of Andoversford lies six miles southeast of Cheltenham, surrounded by lovely countryside, offering many attractive walks with the renowned Cotswold Way and Gloucestershire Way close by. Andoversford has a thriving village...

"Bears Court Barn 1" is a 3 bed holiday Cottage sleeping up to 6 guests in Gloucestershire. Located in the Cotswold Area of Outstanding Natural Beauty, the historic village of Bourton-on-the-Water dates back to Neolithic times with over 100 buildings being Grade II listed or higher. The picturesque high street nestles alongside the...

"Bears Court Barn 4" is a 3 bed holiday Cottage sleeping up to 6 guests in Gloucestershire. Located in the Cotswold Area of Outstanding Natural Beauty, the historic village of Bourton-on-the-Water dates back to Neolithic times with over 100 buildings being Grade II listed or higher. The picturesque high street nestles alongside the...

"Bears Court Barn 5" is a 4 bed holiday Cottage sleeping up to 8 guests in Gloucestershire. Located in the Cotswold Area of Outstanding Natural Beauty, the historic village of Bourton-on-the-Water dates back to Neolithic times with over 100 buildings being Grade II listed or higher. The picturesque high street nestles alongside the...

"5 Bed Cottage in Lower Slaughter" is a 5 bed holiday Cottage sleeping up to 9 guests in Gloucestershire. Additional information and rulesNo dogs allowed - 5 bedrooms – 1 emperor, 2 doubles, 1 twin, 1 single - 3 bathrooms – 1 en-suite bathroom with bath, separate shower and WC, 1 bathroom with shower over bath and WC, 1 shower room...

"Cotswold View" is a 2 bed holiday Cottage sleeping up to 4 guests in Gloucestershire. Bourton-On-The-Water is a small village resting within the Cotswold Area of Outstanding Natural Beauty and dates back to the Neolithic times with over 100 buildings being Grade II listed or higher. As well as a plethora of amenities, the...

"Rissington Hill House" is a 6 bed holiday Cottage sleeping up to 11 guests in Gloucestershire. Rissington Hill House is situated in between some of the most iconic Cotswold towns and villages, Stow-on-the-Wold, Burford and Bourton-on-the-Water are all easily reachable in less than 15-minutes. The closest pub, The Lamb Inn, can be reached...

"Cowley Manor Experimental" is a 1 bed holiday Hotel sleeping up to 2 guests in Gloucestershire.

"The Slaughters Country Inn" is a 1 bed holiday Hotel sleeping up to 3 guests in Gloucestershire.

"Little Rissington - The Couples Retreat" is a 2 bed holiday Apartment sleeping up to 4 guests in Gloucestershire.

"The Slaughters Manor House" is a 1 bed holiday Hotel sleeping up to 4 guests in Gloucestershire.

"Sherbourne Cottage, Seven Springs Cottages" is a 2 bed holiday Cottage sleeping up to 4 guests in Gloucestershire.

"Bill's Cottage" is a 3 bed holiday Cottage sleeping up to 6 guests in Gloucestershire.

"Little Rissington - Barn Two" is a 3 bed holiday Cottage sleeping up to 6 guests in Gloucestershire.

"Belle-Suite" is a 1 bed holiday Apartment sleeping up to 3 guests in Gloucestershire.

"Ashleigh - Ash Farm Cotswolds" is a 3 bed holiday Cottage sleeping up to 6 guests in Gloucestershire.

"The Grove Escape" is a 0 bed holiday Cottage sleeping up to 9 guests in Gloucestershire.

"Cotswold cottage" is a 3 bed holiday Cottage sleeping up to 7 guests in Gloucestershire.

"Little Rissington - Barn Five" is a 4 bed holiday Cottage sleeping up to 8 guests in Gloucestershire.

"The Slaughters Manor House" is a 1 bed holiday Hotel sleeping up to 3 guests in Gloucestershire.