Winchcombe holiday rentalscozycozy

Holiday Rentals in Winchcombe

207 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

207 Holiday rentals and Airbnb in Winchcombe

Chic 1br Cheltenham Apt Near Town Centre - Winchcombe
Winchcombe
1 1
163 â‚¬/nighttotal: 326 â‚¬ (2 )

Chic 1br Cheltenham Apt Near Town Centre

apartment - Cheltenham
This Cheltenham town centre flat is a short walk from the Regent Arcade shopping centre, Everyman and Playhouse Theatres, and a 0.5km taxi ride from Cheltenham Racecourse.
The 46-square-metre self-catering apartment features one bedroom, one bathroom, a private terrace, parking, and sleeps two guests, with a king-size bed, modern kitchen, and smart TV.
Mayville House Flat - Winchcombe
8.1 32 reviews
Winchcombe
1 1
178 â‚¬/nighttotal: 356 â‚¬ (2 )

Mayville House Flat

apartment - Cheltenham
This charming one-bedroom flat is located in a peaceful cul-de-sac in Cheltenham, just a 5-minute walk from the town's shops, restaurants, and theatre. It has received excellent ratings for location, cleanliness, and overall experience.
The 12 square metre flat has a comfortable bedroom with a super king-size bed and a spacious living/dining area with two sofa beds. Guests can enjoy free Wi-Fi, a TV, parking, and a fully equipped kitchen with a washing machine, microwave, fridge, and freezer.
Jaskar Studio 2 - Winchcombe
8.2 125 reviews
Winchcombe
2 1
97 â‚¬/nighttotal: 582 â‚¬ (6 )

Jaskar Studio 2

studio - Cheltenham
Jaskar studio 2 is located in Cheltenham, a short walk from Cheltenham Town Hall and within easy reach of several popular attractions like Sudeley Castle, 8.5 kilometers away, and Cotswold Water Park, 20 kilometers away. The studio has received very good user ratings and excellent location and cleanliness ratings.
The self-contained studio offers a private entrance, a separate living room, and a fully equipped kitchen, all within 6 square meters, and can accommodate up to 2 guests. The studio is equipped with a flat-screen TV, a washing machine, and a walk-in shower, ensuring a comfortable and convenient stay.
Daffodil Suite At Regency 24 - Winchcombe
8.8 8 reviews
Winchcombe
2 1
116 â‚¬/nighttotal: 696 â‚¬ (6 )

Daffodil Suite At Regency 24

apartment - Cheltenham
The Daffodil Suite at Regency 24 is a conveniently located flat in Cheltenham, situated 12.7 kilometres from Sudeley Castle and 13.9 kilometres from Gloucester Cathedral, with Kingsholm Stadium 14.3 kilometres away.
This 30 square metre apartment accommodates up to three guests and offers free WiFi, complimentary on-site parking, and a flat-screen TV, with check-out between 08:00 and 10:00 AM.
Cotswold Retreat - Winchcombe
9.7 127 reviews
Winchcombe
2 1
128 â‚¬/nighttotal: 256 â‚¬ (2 )

Cotswold Retreat

apartment - Cheltenham
Cotswold Retreat, a self-contained apartment in Andoversford, Gloucestershire, is conveniently located 14 kilometres from Sudeley Castle and offers easy access to other Cotswolds attractions.
This one-bedroom flat boasts 14 square metres of floor space, sleeps two guests, and includes free Wi-Fi, private parking, and a terrace.
Elliot Oliver - 2 Bedroom Garden Apartment With Parking - Winchcombe
8.9 176 reviews
Winchcombe
2 2
163 â‚¬/nighttotal: 326 â‚¬ (2 )

Elliot Oliver - 2 Bedroom Garden Apartment With Parking

apartment - Cheltenham
This garden flat is located in Cheltenham, just 29km from Weston Park, 34km from Cotswold Water Park and 47km from Coughton Court, making it a great base for exploring the Cotswolds. It has received very good user and location ratings, and an excellent cleanliness rating.
The flat has two bedrooms, providing space for a small family or group of friends, and is 60 square metres in size. It offers a private garden, dedicated parking, free WiFi and is close to Cheltenham's attractions, including the racecourse and theatre.
F1 Town Centre, Walk To Races! Sleeps 4 - Winchcombe
8.2 20 reviews
Winchcombe
1 1
184 â‚¬/nighttotal: 368 â‚¬ (2 )

F1 Town Centre, Walk To Races! Sleeps 4

apartment - Cheltenham
This Cheltenham apartment, ideally located in a central area, offers convenient access to Sudeley Castle (13 km), Kingsholm Stadium (13.7 km), and Gloucester Cathedral (14.6 km).
The 40 square metre flat features one bedroom, one bathroom, sleeps seven guests, and includes a kitchenette, private parking, and a washing machine.
Stylish Home In The Heart Of Cheltenham - Winchcombe
8.6 28 reviews
Winchcombe
2 2
154 â‚¬/nighttotal: 308 â‚¬ (2 )

Stylish Home In The Heart Of Cheltenham

house - Cheltenham
This Cheltenham house, conveniently located near the town centre, is 13.2 km from Sudeley Castle and 14.2 km from Kingsholm Stadium.
The 20-square-metre property offers two bedrooms, one bathroom, and sleeps up to seven guests, boasting a private garden, parking, Wi-Fi, and a well-equipped kitchen including an oven, toaster, and fridge.
Lovely 2-bed Town Centre Duplex Apartment - Winchcombe
8.9 10 reviews
Winchcombe
2 2
148 â‚¬/nighttotal: 888 â‚¬ (6 )

Lovely 2-bed Town Centre Duplex Apartment

apartment - Gloucestershire
This Cheltenham town centre duplex apartment offers easy access to shops, restaurants, and cultural attractions, lying within 13km of Sudeley Castle and under 15km from Kingsholm Stadium.
The 65 square metre, two-bedroom flat sleeps eight guests and includes a fully equipped kitchen, free Wi-Fi, a flat-screen TV, and parking.
Beautiful Self Contained Studio Home In Rural Toddington - Winchcombe
9.5 11 reviews
Winchcombe
2 1
132 â‚¬/nighttotal: 792 â‚¬ (6 )

Beautiful Self Contained Studio Home In Rural Toddington

studio - Cheltenham
This self-contained loft apartment in Toddington, Gloucestershire, offers a peaceful rural retreat, conveniently located within a 30-kilometre radius of Kingsholm Stadium, the Royal Shakespeare Company, and Coughton Court.
The 46-square-metre studio sleeps three guests and features a fully equipped kitchen with a microwave, one bathroom, free Wi-Fi, and an outdoor dining area.
Pittville Garden Flat - Walk To Town ,Racecourse And Pittville Park - Winchcombe
10 4 reviews
Winchcombe
2 1
142 â‚¬/nighttotal: 284 â‚¬ (2 )

Pittville Garden Flat - Walk To Town ,Racecourse And Pittville Park

apartment - Cheltenham
This garden flat in Cheltenham offers a private garden and terrace with garden views, located 15 kilometres from Kingsholm Stadium and 32 kilometres from Cotswold Water Park.
This spacious one-bedroom apartment accommodates two guests, featuring a fully equipped kitchenette with a fridge, microwave, and dishwasher, complimentary Wi-Fi, an outdoor dining area, and provided towels and bed linen, covering 70 square meters.
2-bedroom House In Cheltenham Town Centre - Winchcombe
9.2 65 reviews
Winchcombe
2 2
130 â‚¬/nighttotal: 780 â‚¬ (6 )

2-bedroom House In Cheltenham Town Centre

apartment - Cheltenham
This Cheltenham town centre flat is conveniently located near Sudeley Castle (12.4 km), Kingsholm Stadium (14.5 km), and Gloucester Cathedral (16.1 km), offering easy access to local attractions.
The 66 square metre self-catering property sleeps up to 11 guests, boasting two bedrooms, one bathroom, a garden, free Wi-Fi, private parking (at an extra charge), and a recently renovated kitchen equipped with a fridge and microwave.

Best family friendly Winchcombe holiday rentals

Among the 207 accommodations in Winchcombe, here are the 4 best family friendly rentals

Chapel End - Winchcombe
10 188 reviews
Winchcombe
1 1
201 â‚¬/nighttotal: 402 â‚¬ (2 )

Chapel End

house
This unique converted chapel dwelling is situated on Cleeve Hill, on the Cotswold Way, a short walk (approximately 0.5km) from the Rising Sun pub and Cleeve Hill Golf Club, with Cheltenham Racecourse also within easy reach.
The one-bedroom property sleeps four, offering a super king bed, a pull-out small double bed, and a travel cot, alongside a kitchen with dining area, conservatory, private courtyard, and a wet room with bath; pets are welcome.
Castle Cottage Winchcombe - Winchcombe
9.5 118 reviews
Winchcombe
2 2
368 â‚¬/nighttotal: 2208 â‚¬ (6 )

Castle Cottage Winchcombe

house - Winchcombe
This charming 19th-century Cotswold cottage is located in Winchcombe, a picturesque town in the Cotswolds, just 15 miles from Gloucester's Kingsholm Stadium and 23 miles from Stratford-upon-Avon's Royal Shakespeare Theatre. The property enjoys excellent ratings for its location, cleanliness, and overall experience.
The cottage features two bedrooms and two bathrooms, comfortably accommodating up to four guests. Enjoy modern amenities like a dishwasher, washing machine, and free Wi-Fi, and explore the beautiful Cotswolds by bike, fishing in nearby rivers, or visiting local attractions like Sudeley Castle and the Cotswold Way National Trail.
Stunning 2 Bedroom Flat In The Centre Of Cheltenham - Winchcombe
Winchcombe
2 2
175 â‚¬/nighttotal: 1050 â‚¬ (6 )

Stunning 2 Bedroom Flat In The Centre Of Cheltenham

apartment - Cheltenham
This two-bedroom maisonette on Berkeley Place, Cheltenham, offers period character within easy walking distance of Montpellier and the town centre, placing you close to independent boutiques, cafes, restaurants, and parks.
This 17 square meter flat accommodates up to three guests, featuring two bedrooms, one bathroom, a fully equipped open-plan kitchen, and amenities including internet and a Nespresso machine, with the Cotswolds accessible for countryside exploration.
A Sudeley Castle Cottage That Sleeps 3 Guests  In 2 Bedrooms - Winchcombe
9.2 83 reviews
Winchcombe
2 2
188 â‚¬/nighttotal: 1128 â‚¬ (6 )

A Sudeley Castle Cottage That Sleeps 3 Guests In 2 Bedrooms

cottage - Cheltenham
This charming cottage is located in a peaceful rural setting just a 10-minute walk from Winchcombe Folk and Police Museum, Belas Knap, and Sudeley Castle, and a short 3.4 km drive from Hailes Abbey. The cottage has received very good user ratings, making it a popular choice for travellers.
The cottage offers two bedrooms, providing comfortable accommodation for up to three guests. You can enjoy amenities such as a fully equipped kitchen, a private patio, and free Wi-Fi, as well as parking and the option of bringing your pet.

Best Winchcombe holiday rentals with parking

The Nook, Fairview, Cheltenham Town Centre-parking & Garden - Winchcombe
9.6 89 reviews
Winchcombe
2 2
172 â‚¬/nighttotal: 1032 â‚¬ (6 )

The Nook, Fairview, Cheltenham Town Centre-parking & Garden

house - Cheltenham
The Nook offers self-catering accommodation in Cheltenham town centre, conveniently located 12.6km from Sudeley Castle and 15km from Kingsholm Stadium.
This two-bathroom house sleeps seven guests, features free Wi-Fi and private parking, and includes a fully equipped kitchen and garden.
Lovely 3 Bed House In The Heart Of Cheltenham - Winchcombe
8.5 310 reviews
Winchcombe
2 3
217 â‚¬/nighttotal: 434 â‚¬ (2 )

Lovely 3 Bed House In The Heart Of Cheltenham

house - Cheltenham
This 3-bedroom house is located in Cheltenham, just 13.7 kilometres from Kingsholm Stadium, offering a convenient base for exploring the town and its surroundings. The property has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable stay.
The house spans 149 square metres and comfortably accommodates up to 6 guests. It offers a range of amenities including a terrace, garden, free Wi-Fi, and a kitchen with a fridge and microwave oven, making it ideal for families or groups of friends.
Elliot Oliver - Deluxe Two Bedroom Apartment With Parking & Ev Charger - Winchcombe
9.2 26 reviews
Winchcombe
2 2
163 â‚¬/nighttotal: 326 â‚¬ (2 )

Elliot Oliver - Deluxe Two Bedroom Apartment With Parking & Ev Charger

apartment - Cheltenham
This recently renovated Cheltenham apartment, located 13.2 km from Sudeley Castle and 13.5 km from Kingsholm Stadium, offers convenient access to local attractions.
The 61 square metre self-catering flat features two bedrooms, two bathrooms, sleeps seven, and includes a fully equipped kitchen with dishwasher, free private parking with EV charger, and free Wi-Fi.
Sudeley Castle Guest Cottage - Winchcombe
9.4 75 reviews
Winchcombe
2 2
283 â‚¬/nighttotal: 566 â‚¬ (2 )

Sudeley Castle Guest Cottage

house - Winchcombe
Sudeley Castle Guest Cottage is a charming house in Winchcombe, just a short drive from Kingsholm Stadium and the Royal Shakespeare Theatre, making it a great base for exploring the Cotswolds. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This comfortable accommodation offers three bedrooms, a living room with a satellite TV, and two bathrooms. Enjoy the patio, barbecue facilities, and garden views, or explore the nearby hiking trails.

Frequently asked questions about holiday rentals in Winchcombe

  • Which walking or cycling routes are the best in Winchcombe?

    There are many great walking and cycling routes around Winchcombe. The Cotswold Way National Trail passes through the town, offering stunning views of the Cotswolds. The Cotswold Canals towpath is another good option, and you can also cycle along the scenic roads around the town. The Cotswold Way is particularly popular, and the views are incredible, especially from the top of Belas Knap long barrow.
  • What are the best Airbnb and holiday rentals in Winchcombe?

  • What sports or outdoor activites can visitors enjoy in and around Winchcombe?

    Winchcombe is a great place for outdoor activities. You can go walking, cycling, horse riding, or play golf at the nearby Cotswold Hills Golf Club. You can also enjoy fishing in the River Avon or visit the Cotswold Water Park for watersports. There's a lot to do in the area, and you can find something for everyone.
  • What are the most popular Airbnbs in Winchcombe?

  • What other towns or cities can be easily accessed from Winchcombe?

    Winchcombe is well-connected to other towns and cities in the Cotswolds. You can easily visit Cheltenham, Gloucester, and Stratford-upon-Avon by car or bus. You can also take a train from nearby stations like Cheltenham Spa or Moreton-in-Marsh. It's a great base for exploring the Cotswolds, and you can easily reach other towns and cities within a short distance.
  • What are the best holiday rentals with a pool in Winchcombe?

    The best holiday rental with a pool in Winchcombe is Peaceful Cottage In Heart Of Winchcombe.

  • What amenities are commonly available in vacation rentals in Winchcombe?

    Most vacation rentals in Winchcombe offer basic amenities like Wi-Fi, a kitchen, and a bathroom. Some rentals also have a garden, parking, and a washing machine. You can find rentals that suit your needs and budget, and you can usually find information about the amenities on the rental website. There are also a few hotels in Winchcombe.
  • What are the best rentals for families and kids in Winchcombe?

    The best rentals for families and kids in Winchcombe are The Cottage And The Nook, No61 Winchcombe (Cotswolds) and Emma Dent.

  • What time of year is best to rent a vacation rental Winchcombe?

    The best time to visit Winchcombe depends on your preferences. Spring and autumn are lovely, with mild temperatures and beautiful colours. Summer is warm and sunny, perfect for outdoor activities. Winter can be chilly but offers a charming atmosphere. The town is beautiful all year round, so you can visit whenever suits you best.
  • What are the best rentals or Airbnbs with a jacuzzi in Winchcombe?

    The best vacation rentals or Airbnb with a jacuzzi in Winchcombe are Cosy Cotswold Lodge With Private Garden & Hot Tub, The Old Forge and Luxury Cotswolds Cottage With Hot Tub.

Popular destinations

Best Winchcombe holiday rentals with a balcony

Stylish Flat With Terrace In Cheltenham Centre - Winchcombe
8.7 13 reviews
Winchcombe
2 1
162 â‚¬/nighttotal: 324 â‚¬ (2 )

Stylish Flat With Terrace In Cheltenham Centre

apartment - Cheltenham
This Cheltenham Centre flat offers convenient access to local amenities and is situated 13.4 kilometres from Sudeley Castle and 13.9 kilometres from Gloucester Cathedral.
This 46 square metre one-bedroom flat accommodates up to three guests, featuring a fully equipped kitchen, private terrace, complimentary WiFi, and on-site parking.
The Annexe - Winchcombe
9.2 68 reviews
Winchcombe
2 1
125 â‚¬/nighttotal: 250 â‚¬ (2 )

The Annexe

apartment - Cheltenham
The Annexe is a charming one-bedroom apartment located in Cheltenham, just a short drive from the historic Gloucester Cathedral and within easy reach of the Cotswold Water Park. It has received excellent ratings for its location, cleanliness, and overall experience.
This self-catering flat has a private entrance and can comfortably accommodate two guests. It features a terrace with darts, a private garden, and free parking, as well as a sustainable design and free WiFi.
Stunning 2 Bed Basement Flat In The Heart Of Cheltenham! - Winchcombe
9.4 63 reviews
Winchcombe
2 2
253 â‚¬/nighttotal: 506 â‚¬ (2 )

Stunning 2 Bed Basement Flat In The Heart Of Cheltenham!

apartment - Cheltenham
This Cheltenham basement flat, situated 14.3 kilometres from Kingsholm Stadium and conveniently close to other attractions, offers a central location ideal for exploring the town. This two-bedroom, two-bathroom apartment boasts 98 square metres of living space, including a fully equipped kitchen, private terrace, garden, parking, and free Wi-Fi.
Lady Jane Grey - Winchcombe
9.6 50 reviews
Winchcombe
2 3
314 â‚¬/nighttotal: 628 â‚¬ (2 )

Lady Jane Grey

house - Winchcombe
Lady Jane Grey is a charming house in Winchcombe, Gloucestershire, just a short drive from Kingsholm Stadium and the Royal Shakespeare Theatre. This property has received excellent ratings for location, cleanliness and overall experience.
The three-bedroom house is ideal for families or groups of up to five guests and offers 86 square metres of comfortable living space. The property includes a fully equipped kitchen, a terrace with river views, a garden with an outdoor dining area, and free private parking.

Best pet friendly Winchcombe holiday rentals

Among the 207 accommodations in Winchcombe, here are the 4 best pet friendly rentals

Cotswold Detached Hillside Cottage Packed With Quirky Character - Winchcombe
9.4 208 reviews
Winchcombe
2 2
183 â‚¬/nighttotal: 366 â‚¬ (2 )

Cotswold Detached Hillside Cottage Packed With Quirky Character

cottage - Cheltenham
This charming cottage is located in Cheltenham, within a 5km radius of Cleeve Hill Golf Club, Prescott Speed Hill Climb, and Belas Knap, with Winchcombe Folk and Police Museum also within easy reach. The cottage has received excellent ratings for user experience, location, and cleanliness.
The cottage has two bedrooms and two bathrooms, accommodating up to four guests. The property offers a range of amenities, including a fully equipped kitchen, a private garden, a terrace, and a spa tub, making it ideal for a relaxing and comfortable stay.
Charming Cottage In Winchcombe In The Cotswolds - Winchcombe
9.6 166 reviews
Winchcombe
1 2
265 â‚¬/nighttotal: 530 â‚¬ (2 )

Charming Cottage In Winchcombe In The Cotswolds

apartment
This charming apartment is conveniently located just a minute's walk from the heart of Winchcombe, putting you within easy reach of the town's shops, pubs, and restaurants. It has consistently received excellent ratings for location, cleanliness, and overall experience.
The apartment comfortably sleeps four guests and features two bedrooms and a bathroom. It comes equipped with a modern kitchen, a cosy living area, a private garden, and parking, making it ideal for a relaxing and comfortable stay.
The Shepherd Hut, Ford. Cheltenham - Winchcombe
9.9 176 reviews
Winchcombe
1 1
118 â‚¬/nighttotal: 236 â‚¬ (2 )

The Shepherd Hut, Ford. Cheltenham

cabin
This Shepherd's Hut is situated in the Cotswolds, a short 10-minute drive from Bourton-on-the-Water, Stow-on-the-Wold, and Winchcombe.
The cosy hut features a double bed, a Belfast sink, storage benches, and a dining table for four, and includes access to a charming summer house within the courtyard.
Montpellier At Regency 24 - Winchcombe
8.5 10 reviews
Winchcombe
2 1
184 â‚¬/nighttotal: 1104 â‚¬ (6 )

Montpellier At Regency 24

apartment - Cheltenham
This Montpellier flat at Regency 24 in Cheltenham is located 14.3 kilometres from Kingsholm Stadium and 12.7 kilometres from Sudeley Castle, offering convenient access to local attractions.
This 50 square meter apartment accommodates up to seven guests and features a private balcony, complimentary private parking, free WiFi, and a fully equipped kitchen, with check-out between 08:00 and 10:00 AM.
©2026 cozycozy.com