The 25 best holiday rentals in Winchester

#1 of 50 Holiday rentals in Winchester

• “Lovely well equipped cottage with a gorgeous garden”
• “The perfect base to explore Winchester from”
• “Superb find and great stay.”
• See more reviews of Hang Your Hat

#2 of 50 Holiday rentals in Winchester

• “great flat, central location with everything you could need and more!”
• “Perfect location clean comfortable and good value”
• “Very central stay in comfortable apartment”
• See more reviews of City Apartment

#3 of 50 Holiday rentals in Winchester

• “Perfect home from home”
• “Loved it, loved it, loved it!”
• “Sky Penthouse Winchester”
• See more reviews of The Sky Penthouse

#4 of 50 Holiday rentals in Winchester

• “Enjoyed it very much.”
• “Thoughtful, communicative hosts. Great shower.”
• “Comfortable place to stay, great location.”
• See more reviews of Two Bare Feet

#5 of 50 Holiday rentals in Winchester

• “All you need when staying in Winchester”
• “I wish every property was like this - perfect”
• “beautiful home, highly reccomend”
• See more reviews of Sky View

#6 of 50 Holiday rentals in Winchester

• “Amazing place.”
• “Location”
• “Super quirky house , lovely location and very hand for a...”
• See more reviews of Millstream House

#7 of 50 Holiday rentals in Winchester

• “Lovely outlook on to the village green”
• “Easy for Winchester”
• “Really well set up and comfortable loft type accommodation...”
• See more reviews of Idyllic Studio Flat

#8 of 50 Holiday rentals in Winchester

• “Good location close to town.”
• “Great weekend away.”
• “Perfect house for a weekend in Winchester!”
• See more reviews of 4 Bed City House with Private Garden and Parking

#9 of 50 Holiday rentals in Winchester

• “Great stay in Winchester in comfortable and very convenient self-catering house.”
• “A very comfortable, well furnished property, with off road parking and close to all amenities.”
• “Lovely house in excellent location to town centre .”
• See more reviews of South House

#10 of 50 Holiday rentals in Winchester

• “Stylish and comfy centrally located apartment :)”
• “Excellent location, dedicated parking, well-equipped and...”
• “Loved it, would use it again”
• See more reviews of No 3 Old Printworks

#11 of 50 Holiday rentals in Winchester

• “A beautiful gem”
• “Great find, fully equipped and a stone’s throw from the City centre.”
• “Wonderful stay”
• See more reviews of Walsingham House - Peaceful Elevated - Near Oram's Arbour

#12 of 50 Holiday rentals in Winchester

• “Fantastic stay with Finn welcoming us each step of the way.”
• “Lovely flat with everything you could need.”
• “A lovely 1 month stay”
• See more reviews of Boscobel Apartments Up

#13 of 50 Holiday rentals in Winchester

• “Lovely little place ”
• “Left alone to do what I wanted.”
• “Perfect stay in lovely location and very accommodating”
• See more reviews of The Barrel Room at The Northbrook Arms

#14 of 50 Holiday rentals in Winchester

• “A home away from home for a month - exceptional property”
• “The location was fabulous.”
• “This is beautiful property with everything that we needed.”
• See more reviews of House situated on River Itchen

#15 of 50 Holiday rentals in Winchester

• “A lovely little apartment, clean and comfortable. Hosts were happy to check in with us and answer any queries. Would hap”
• “A nice apartment close to the city center.”
• “It was ok but see above”
• See more reviews of The Apartment, 24 West End Terrace, Winchester

#16 of 50 Holiday rentals in Winchester

• “Gorgeous place, helpful hosts”
• “The location was perfect—a lovely, tranquil countryside...”
• “Lovely location, nice house, very clean”
• See more reviews of Watley Farm

#17 of 50 Holiday rentals in Winchester

• “Lovely home very central and on the river”
• “Excellent lovely clean property well presented everything you could possibly want x”
• “Happy Jane Austen trip.”
• See more reviews of Beautiful house on the River Itchen

#18 of 50 Holiday rentals in Winchester

• “A true home from home, the ideal bolt-hole to explore Wonderful Winchester!!”
• “The cottage is beautiful and exceptionally well furnished.”
• “I have stay in a lot of holiday homes and one was by far...”
• See more reviews of Mallard Cottage

#19 of 50 Holiday rentals in Winchester

• “Very pleasant quaint, old cottage close to the town centre.”
• “Great little cottage, very comfortable, had everything you...”
• “Really enjoyable stay, perfect for our needs.”
• See more reviews of Beggar's Lane Cottage

#20 of 50 Holiday rentals in Winchester

• “Lovely house in Winchester”
• “The Nestle House is a top-rated short term stay for a reason!”
• “Perfect. Julia is a wonderful hostess.”
• See more reviews of The Nestle House

#21 of 50 Holiday rentals in Winchester

• “Fiona, the host, was very helpful, and provided extra dining...”
• “Very spacious and clean.”
• “We had a great time in Winchester and found the apartment ideal for our reunion.”
• See more reviews of Garden Apartment Winchester

#22 of 50 Holiday rentals in Winchester

• “Lovely relaxing short break”
• “Proximity to town and services”
• “Great!”
• See more reviews of Boscobel Apartments Down

#23 of 50 Holiday rentals in Winchester

• “Our second visit, convenient for visiting National Trust properties in the Hampshire area.”
• “Would love to stay again”
• “wonderful places!”
• See more reviews of Paddock View

#24 of 50 Holiday rentals in Winchester

• “Fabulous property”
• “Really good space for what you need”
• “Comfortable and very warm and cosy”
• See more reviews of Paddock Drive

#25 of 50 Holiday rentals in Winchester

• “Great location good size”
• “Amazing comfortable stay in the heart of Winchester close to Cathedral and the Christmas Market”
• “Noisy and smelly”
• See more reviews of Perfect Perch for Legal Eagle - Winchester Law Courts, High St, Westgate Museum