This Cheltenham guest annexe is situated less than 100 metres from Cheltenham Race Course and a 10-minute walk (approximately 0.8 km) from Cheltenham town centre, offering easy access to shops, restaurants, and attractions. This self-contained property boasts two double bedrooms, accommodating up to four guests, and includes a fully equipped kitchen, garden, fitness centre, secure parking, EV charging (surcharge applies), and bike storage; access to laundry facilities and a home gym is also available (subject to availability).
9.1 90 reviews
Winchcombe
21/06 – 23/06
NZ$582/nighttotal: NZ$1164 (2 )
Princess Elizabeth
2 3
house , Winchcombe
Princess Elizabeth is a holiday home located just 9 minutes' walk from Sudeley Castle, a historic landmark in Winchcombe, and within easy reach of Cotswold Water Park (43 km) and Charlecote Park (38 km). The property has consistently received excellent ratings for location, cleanliness, and overall user experience. The home has 2 bedrooms and 1 bathroom, comfortably accommodating up to 4 guests. Guests can enjoy a fully equipped kitchen, a private garden with a patio for outdoor dining, free parking, and free Wi-Fi.
9.7 167 reviews
Winchcombe
21/06 – 23/06
NZ$400/nighttotal: NZ$800 (2 )
Chic Apt In Central Cheltenham
1 3
apartment , Cheltenham
This charming one-bedroom flat is ideally located in central Cheltenham, just a short drive from attractions like Sudeley Castle and Gloucester Cathedral. The property has received excellent ratings for location, cleanliness and user experience, ensuring a comfortable and enjoyable stay. The apartment comfortably sleeps four guests and features a fully equipped kitchen, a modern bathroom, and a relaxing living space. Guests can enjoy free Wi-Fi, a flat-screen TV, a Jacuzzi, parking, and the option to bring their pets along.
8.8 12 reviews
Winchcombe
21/06 – 23/06
NZ$366/nighttotal: NZ$732 (2 )
Central Cheltenham Spacious 2-bedroom Apartment - Priory Street
2 3
apartment , Cheltenham
This Cheltenham apartment, situated approximately 83km from Bristol Airport, offers a peaceful retreat outside the town centre. The 1300 square metre property features two bedrooms, one bathroom, sleeps nine guests, and includes free Wi-Fi, parking, and a fully equipped kitchen.
9.3 95 reviews
Winchcombe
21/06 – 23/06
NZ$566/nighttotal: NZ$1132 (2 )
Oliver Cromwell
2 3
apartment , Winchcombe
This Winchcombe apartment is conveniently located just 16 miles from Kingsholm Stadium and within easy reach of Cotswold Water Park and Coughton Court. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience. The apartment has two bedrooms, two bathrooms with walk-in showers, a living room with a flat-screen TV, and a fully equipped kitchen with a dining area. Guests can enjoy free Wi-Fi, private parking, a washing machine, and the option to rent bicycles for exploring the beautiful countryside surrounding Winchcombe.
10 198 reviews
Winchcombe
21/06 – 23/06
NZ$338/nighttotal: NZ$676 (2 )
Entire Residential Home - Town Centre, Ideal Races
1 3
apartment , Gloucestershire
This Cheltenham town centre house, a short walk from Cheltenham Racecourse via Pittville Park, offers excellent location ratings and is close to the park's picturesque walks. Sleeping four guests comfortably in two bedrooms with a super king and double bed, the property features a spacious walk-in shower, jacuzzi bath, electric reclining sofas, a garden, free on-street parking, and a fully equipped kitchen including a fridge, freezer and microwave.
9.6 121 reviews
Winchcombe
21/06 – 23/06
NZ$419/nighttotal: NZ$838 (2 )
Homelands Apartment
1 3
apartment , Cheltenham
Homelands Apartment is situated in Cheltenham, just 19.3 km from Kingsholm Stadium and 40.2 km from Cotswold Water Park, offering mountain views and easy access to local attractions. This guest house has received excellent ratings for its location, cleanliness, and overall experience. The apartment is 20 square metres in size and features a modern bathroom, a comfortable living area with a satellite flat-screen TV, and a kitchen equipped with a fridge, freezer, microwave oven, and dishwasher. Guests can enjoy a terrace or balcony, a garden, free private parking, and a concierge service, as well as free Wi-Fi, room service, and a restaurant.
9.4 59 reviews
Winchcombe
21/06 – 23/06
NZ$330/nighttotal: NZ$660 (2 )
The Snug Central Cosy Good Wi-fi
2 3
house , Cheltenham
The Snug Central Cosy Good Wi-Fi is located in Cheltenham, just 13km from Kingsholm Stadium and 34km from Cotswold Water Park. This property has received excellent ratings for location, cleanliness, and overall user experience. This 2-bedroom house, spanning 49 square meters, comfortably accommodates up to 4 guests. You'll find a fully equipped kitchen with a fridge, microwave oven, and dishwasher, along with a terrace or balcony, parking, and free Wi-Fi, perfect for a relaxing stay.
9.0 18 reviews
Winchcombe
21/06 – 23/06
NZ$304/nighttotal: NZ$608 (2 )
Stylish Home In The Heart Of Cheltenham
2 3
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.
9.8 100 reviews
Winchcombe
21/06 – 23/06
NZ$391/nighttotal: NZ$782 (2 )
Thornton House Luxury Accommodation In The Town Centre With Private Parking
1 3
apartment , Cheltenham
This recently renovated Cheltenham town centre flat offers free private parking, a significant advantage given limited availability, and is conveniently located 12.7km from Sudeley Castle and 13.7km from Kingsholm Stadium. The 70 square metre self-catering apartment features one bedroom, one bathroom, sleeps seven guests, and includes a fully equipped kitchen with dishwasher, a private terrace with city views, and free Wi-Fi.
8.8 43 reviews
Winchcombe
21/06 – 23/06
NZ$413/nighttotal: NZ$826 (2 )
Central Cheltenham, Regency 1st Floor Apartment With Parking, Cavalier Suite - Sleeps 6
2 3
apartment , Cheltenham
The Cavalier Suite is a Regency apartment in central Cheltenham, just 7.7 kilometres from Sudeley Castle and within easy walking distance of the town's shops, restaurants, and attractions. Guests consistently rate it highly for its cleanliness, location, and overall experience. This two-bedroom apartment spans 55 square metres and comfortably accommodates up to six guests. The Cavalier Suite offers a fully equipped kitchen, free parking, garden views, free Wi-Fi, and a comfortable living space with a flat-screen TV.
Among the 124 accommodations in Winchcombe, here are the 4 best family friendly rentals
9.2 81 reviews
Winchcombe
21/06 – 23/06
NZ$543/nighttotal: NZ$1086 (2 )
A Sudeley Castle Cottage That Sleeps 3 Guests In 2 Bedrooms
2 3
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.
This Cheltenham holiday home is situated 0.8km from Jonny-Rocks Stadium and 3km from Cheltenham Racecourse, offering easy access to the Holst Birthplace Museum and Pittville Park, all within a 1.6km radius. The two-bedroom property sleeps four, boasting a fully equipped kitchen with dishwasher, a jacuzzi, garden with barbecue, Smart TV, and fireplace; express check-in/out is available.
9.6 49 reviews
Winchcombe
21/06 – 23/06
NZ$640/nighttotal: NZ$1280 (2 )
Lady Jane Grey
1 3
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.
8.2 28 reviews
Winchcombe
21/06 – 23/06
NZ$392/nighttotal: NZ$784 (2 )
Mayville House Flat
1 3
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.
Best Winchcombe holiday rentals with parking
9.2 125 reviews
Winchcombe
21/06 – 23/06
NZ$582/nighttotal: NZ$1164 (2 )
Lord High Admiral
2 3
apartment , Winchcombe
This Winchcombe apartment is conveniently located just 26km from Kingsholm Stadium and 37km from the Royal Shakespeare Theatre, offering easy access to both sporting and cultural attractions. Guests consistently rate the apartment highly, praising its excellent location, cleanliness and overall experience. The self-catering property has two bedrooms, a living room and two bathrooms, making it suitable for families or groups of up to four people. Guests can enjoy a private terrace with garden views, a fully equipped kitchen, free parking and Wi-Fi, as well as the opportunity to explore the picturesque surrounding countryside on foot or by bike.
9.3 27 reviews
Winchcombe
21/06 – 23/06
NZ$475/nighttotal: NZ$950 (2 )
Unique & Stylish Town House In Central Cheltenham
2 3
house , Cheltenham
This stylish Cheltenham townhouse is centrally located, offering easy access to Sudeley Castle (13 km), Gloucester Cathedral (13.7 km), and Kingsholm Stadium (14 km). The 79 square metre property features two bedrooms, two bathrooms, and accommodates up to nine guests, boasting a private terrace, fully equipped kitchen, free Wi-Fi, and parking.
9.4 197 reviews
Winchcombe
21/06 – 23/06
NZ$334/nighttotal: NZ$668 (2 )
Cotswold Detached Hillside Cottage Packed With Quirky Character
2 3
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.
9.4 3 reviews
Winchcombe
21/06 – 23/06
NZ$521/nighttotal: NZ$1042 (2 )
Stunning 2 Bed In The Heart Of Cheltenham
2 3
apartment , Cheltenham
This centrally located Cheltenham apartment is within a 2.4km walk of Cheltenham General Hospital, the Playhouse Theatre, Everyman Theatre, Cheltenham Town Hall, and Imperial Gardens. The two-bedroom, two-bathroom flat sleeps four guests and boasts a fully equipped kitchen, private enclosed yard, free Wi-Fi, and on-site parking.
Frequently asked questions about holiday rentals in Winchcombe
What are some interesting places to visit in or near Winchcombe?
Winchcombe is a charming town with plenty to see! You can visit the historic Sudeley Castle, explore the Cotswold Farm Park, or learn about the history of aviation at the Cotswold Airport. If you want to venture a bit further, you could visit the Roman city of Gloucester, which is only about a 20 minute drive away.
What are the best Airbnb and holiday rentals in Winchcombe?
Which walking or cycling routes are the best in Winchcombe?
There are some lovely walks around Winchcombe, like the Cotswold Way, which offers stunning views of the countryside. For cyclists, the Cotswold Cycleway is a popular route that runs through the area. You can also explore the many smaller lanes and paths that wind through the countryside.
What sports or outdoor activites can visitors enjoy in and around Winchcombe?
Winchcombe is great for outdoor activities! You can go for a hike in the Cotswolds, play a round of golf at the Cotswold Hills Golf Club, or go horse riding at one of the local riding schools. There are also plenty of opportunities for fishing in the local rivers and streams.
What are the best holiday rentals with a pool 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 reach Cheltenham, Gloucester, and Stratford-upon-Avon by car or bus. If you want to explore further afield, you could take a train to Oxford or Birmingham.
What are the best rentals for families and kids in Winchcombe?
What amenities are commonly available in vacation rentals in Winchcombe?
Vacation rentals in Winchcombe usually have all the basics, like a kitchen, bathroom, and bedrooms. Some might also offer extras like a garden, a fireplace, or a hot tub. It really depends on the specific property.
What are the best rentals or Airbnbs with a jacuzzi in Winchcombe?
What time of year is best to rent a vacation rental Winchcombe?
Winchcombe is lovely all year round, but it's particularly popular during the spring and summer months when the weather is warm and sunny. You can enjoy the beautiful countryside and all the outdoor activities on offer. Autumn is also a great time to visit, with the changing colours of the leaves.
What are the local dishes in Winchcombe region?
The Cotswolds is known for its hearty, traditional English food. You can find plenty of pubs and restaurants serving classic dishes like roast dinners, fish and chips, and steak and ale pie. There are also some great local cheeses and beers to try.
Destinations nearby
Best Winchcombe holiday rentals with a balcony
9.2 6 reviews
Winchcombe
21/06 – 23/06
NZ$602/nighttotal: NZ$1204 (2 )
Prince Rupert
2 3
apartment , Winchcombe
Prince Rupert apartment, a two-bedroom flat in Winchcombe, Gloucestershire, is situated 24 kilometres from Kingsholm Stadium and 37 kilometres from the Royal Shakespeare Theatre, offering easy access to Cotswold attractions. This 70 square metre self-catering property sleeps five, boasting a fully equipped kitchen (fridge, microwave, dishwasher), private balcony, garden, parking, Wi-Fi, and a baby safety gate; nearby hiking trails add to its appeal.
9.6 6 reviews
Winchcombe
21/06 – 23/06
NZ$415/nighttotal: NZ$830 (2 )
Cheltenham Town Centre With Parking Space
1 3
house , Cheltenham
This Cheltenham townhouse is located centrally, providing easy access to local amenities and is 12.4 kilometres from Sudeley Castle and 14.2 kilometres from Kingsholm Stadium. This property offers WiFi, a kitchen, and parking for up to 13 guests, with 2 bathrooms and 1 bedroom.
8.5 2 reviews
Winchcombe
21/06 – 23/06
NZ$375/nighttotal: NZ$750 (2 )
The Chapel Street Hideaway By Fortuna Property Portfolio
1 3
house , Cheltenham
This Cheltenham vacation home is located 14 kilometres from Kingsholm Stadium and 32 kilometres from Cotswold Water Park. This 81 square metre holiday home offers a fully equipped kitchen, free WiFi, and free parking, with a terrace and garden for outdoor enjoyment, accommodating up to 13 guests.
8.8 3 reviews
Winchcombe
21/06 – 23/06
NZ$407/nighttotal: NZ$814 (2 )
Modern & Spacious Home In Central Cheltenham
3 3
apartment , Gloucestershire
This Cheltenham holiday home is situated less than 1.6km from Cheltenham Art Gallery & Museum, Cineworld Cheltenham, and The Promenade, offering easy access to Cheltenham Spa railway station (1.4km). The three-bedroom property boasts three bathrooms, a fully equipped kitchen including dishwasher and washing machine, and comfortably accommodates six guests in a smoke-free environment with convenient parking.
Best pet friendly Winchcombe holiday rentals
Among the 124 accommodations in Winchcombe, here are the 4 best pet friendly rentals
9.9 103 reviews
Winchcombe
21/06 – 23/06
NZ$459/nighttotal: NZ$918 (2 )
Cotswold Cottage, Near Broadway
1 3
apartment , Wormington
This contemporary Victorian barn conversion is situated in the peaceful village of Wormington, just 10km from the popular Cotswold destinations of Broadway, Winchcombe, and Cheltenham. The property has received excellent ratings for its location, cleanliness, and overall experience, making it a great choice for travelers seeking a comfortable and relaxing stay. The charming cottage offers two bedrooms, accommodating up to four guests, with a modern bathroom, a well-equipped kitchen, and a private garden with parking for two vehicles. Guests can enjoy the peaceful surroundings, explore the Cotswolds on foot or by bike, and take advantage of the nearby attractions, including the picturesque village church and the surrounding hills.
10 618 reviews
Winchcombe
21/06 – 23/06
NZ$355/nighttotal: NZ$710 (2 )
Charming Dog Friendly Barn Conversion & Paddock
1 3
apartment , Bank Farm Barns
Hare Barn, a charming converted barn, is situated in a rural Area of Outstanding Natural Beauty, just a short drive from the picturesque village of Bredon, with its historic church and traditional pub. It boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay. The one-bedroom barn offers a spacious open-plan living area with a vaulted ceiling and a cosy wood burner, perfect for couples seeking a peaceful retreat. Guests can enjoy a private patio with breathtaking views, a fully fenced paddock ideal for dogs, and access to a network of footpaths for exploring the surrounding countryside.
8.6 10 reviews
Winchcombe
21/06 – 23/06
NZ$543/nighttotal: NZ$1086 (2 )
Prince Rupert, Sudeley Castle, Cotswolds
1 3
apartment , Winchcombe
Prince Rupert cottage, a dog-friendly apartment in Winchcombe, Gloucestershire, is located a short walk from the town centre and Sudeley Castle. This two-bedroom self-catering property sleeps up to three guests plus an infant, offering a fully equipped kitchen with a dishwasher and Nespresso machine, plus free Sudeley Castle & Gardens entry (excluding special events) and access to local discounts.
9.2 21 reviews
Winchcombe
21/06 – 23/06
NZ$543/nighttotal: NZ$1086 (2 )
Charles I, Sudeley Castle, Cotswolds
1 3
apartment , Winchcombe
Charles I cottage is located in Winchcombe, a short walk from the town centre and Sudeley Castle, offering a peaceful setting close to local attractions. The property has received excellent ratings for its location, cleanliness, and overall experience. The cottage is a two-bedroom apartment that can accommodate up to three guests. It is equipped with modern amenities, including a fully equipped kitchen, a private seating area, and a shared decking area with views of the garden and woodland.