The 19 best holiday rentals in Winchester

#1 of 48 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 48 Holiday rentals in Winchester

• “We all had a lovely break and the location is superb.”
• “Beautiful, super-comfortable flat with excellent hosts”
• “Great location and a brilliant flat.”
• See more reviews of City Apartment

#3 of 48 Holiday rentals in Winchester

• “Loved it, loved it, loved it!”
• “Sky Penthouse Winchester”
• “Beautiful apartment”
• See more reviews of The Sky Penthouse

#4 of 48 Holiday rentals in Winchester

• “Comfortable place to stay, great location.”
• “Exceptional”
• “A memorable and wonderful stay”
• See more reviews of Two Bare Feet

#5 of 48 Holiday rentals in Winchester

• “Lovely setting overlooking gardens, large stream. Walkable to everything. Wish we could've stayed”
• “The house is beautiful and the location is great and central...”
• “Thoroughly recommend this cottage for a visit to Winchester and around the area”
• See more reviews of Millstream House

#6 of 48 Holiday rentals in Winchester

• “Really well set up and comfortable loft type accommodation...”
• “A hidden gem. The hosts were lovely, detail oriented and treated me like a personal guest.”
• “Well equipped studio.”
• See more reviews of Idyllic Studio Flat

#7 of 48 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

#8 of 48 Holiday rentals in Winchester

• “Lovely house in excellent location to town centre .”
• “Perfect location, perfect accommodation”
• “Convenient for Winchester, comfortable house.”
• See more reviews of South House

#9 of 48 Holiday rentals in Winchester

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

#10 of 48 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 48 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 48 Holiday rentals in Winchester

• “Lovely flat with everything you could need.”
• “A lovely 1 month stay”
• “Winchester, boscobel apartment”
• See more reviews of Boscobel Apartments Up

#13 of 48 Holiday rentals in Winchester

• “Left alone to do what I wanted.”
• “Perfect stay in lovely location and very accommodating”
• “Nice place for a night stop, like we did. But any longer for two people you would need more space.”
• See more reviews of The Barrel Room at The Northbrook Arms

#14 of 48 Holiday rentals in Winchester

• “It was ok but see above”
• “Great accomodation, brilliant hosts, can’t wait to go back!”
• “Loved Winchester though with a wheelchair it has it's challenges.”
• See more reviews of The Apartment, 24 West End Terrace, Winchester

#16 of 48 Holiday rentals in Winchester

• “The location was fabulous.”
• “This is beautiful property with everything that we needed.”
• “Perfect”
• See more reviews of House situated on River Itchen

#17 of 48 Holiday rentals in Winchester

• “The location was perfect—a lovely, tranquil countryside...”
• “Lovely location, nice house, very clean”
• “Lovely time but host needs to address the minor easily fixed flaws.”
• See more reviews of Watley Farm

#18 of 48 Holiday rentals in Winchester

• “Excellent lovely clean property well presented everything you could possibly want x”
• “Happy Jane Austen trip.”
• “Comfortable home from home for exploring Winchester”
• See more reviews of Beautiful house on the River Itchen

#19 of 48 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

#20 of 48 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