
Holiday rentals in City of Winchester
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Top-rated holiday rentals in City of Winchester
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in City of Winchester
Top guest favourite

Guest suite in Chandler's Ford
4.94 out of 5 average rating, 122 reviewsPrivate detached en-suite annexe
PhoebeRating, 5 stars1 week ago
Easy to check in, was a lovely clean space with full amenities Would happily book again :)
Guest favourite

Guest house in Hampshire
4.91 out of 5 average rating, 44 reviewsPrivate garden room, free permit parking
HannahRating, 5 stars1 week ago
Stayed at Sune’s for an event In Winchester. Such a beautiful place to stay, the cleanest and most well kept place I’ve ever stayed. Lovely quiet location and easy walk into the city centre. Sune was so helpful and quick to respond to messages. I would absolutely recommend.
Top guest favourite

Guest house in Shirley
4.98 out of 5 average rating, 124 reviewsCity Retreat
KarenRating, 5 stars3 weeks ago
Perfect location for the hospital. Stayed one night with my husband and the second night alone whilst he was in hospital. The location felt very safe and it was nice that I could sit out in the pretty garden.
Guest favourite

Tiny home in Winchester
4.83 out of 5 average rating, 458 reviewsCosy rural hideaway, Hursley, near Winchester
KevinRating, 5 stars1 month ago
From booking to arrival Kirsten couldn’t have been more helpful. Kirsten recommended some lovely places in the new forest & was very friendly. The tiny house is absolutely gorgeous & looks just like the photos.
Top guest favourite

Tiny home in Soberton
4.97 out of 5 average rating, 282 reviewsSelf-contained Garden Cottage in idyllic location
TaraRating, 5 stars2 days ago
I had the most peaceful and relaxing stay at River Dale Garden Cottage with my two rescue dogs. From the moment we arrived, we felt completely at ease, it’s a true little haven nestled in the most beautiful surroundings. The cottage itself is spotless, cosy, and thoughtfully designed with everything you could possibly need. The garden is full of charm, and the path leading up to the cottage adds to its magical feel. The location is absolutely perfect. Just a short stroll to the River Meon and the scenic Meon Trail, it’s ideal for anyone who enjoys walking, nature or simply unwinding in a truly tranquil setting. I loved how easy it was to explore the surrounding towns, but also how lovely it was to just stay put and enjoy the peace and quiet. I also recommend the walk to the local pub through the fields, really good food and dog-friendly. Ali was a fantastic host- friendly, helpful and respectful of my privacy. It’s clear she cares deeply about making her guests feel welcome.
Top guest favourite

Flat in Winchester
4.95 out of 5 average rating, 324 reviewsCentral Winchester garden flat, permit parking
NicholasRating, 5 starstoday
A wonderfully warm welcome and briefing from Richard. The flat was small but perfectly-formed, with its own garden area. It was very well-equipped, comfortable and attractively furnished and decorated. The attention to detail was impressive, with thoughtful touches like flowers and basic supplies. The free permit-parking was convenient, and the city centre within easy walking distance. Even during a heat-wave, the flat remained cool, and the busy street was, as advertised, peaceful at night. We will certainly return if we’re back in the area. Thank you to Richard and Kate.
Guest favourite

Guest house in Hampshire
4.93 out of 5 average rating, 92 reviewsCentral, Quiet & Self-Contained
JordanRating, 5 stars1 week ago
This place was great! Very centrally located - a bit of a walk to the train, but centrally located in Winchester. The city lace is super clean and cute, the only is that the WiFi was a bit unreliable at times and I needed to make a few calls using data. Would definitely stay again.
Top guest favourite

Guest house in Winchester
4.97 out of 5 average rating, 518 reviewsIdyllic Hideaway Ham Green Cottage near Winchester
MaeRating, 5 stars3 weeks ago
A lovely little cottage to stay in for some peace and quiet. The perfect distance from Winchester where you can appreciate both the City and the countryside. The walks around the town were gorgeous and the house had everything we needed. It was so clean and was beautifully decorated. Could not recommend enough. So good for the price!!!
Quick stats about holiday rentals in City of Winchester
Total rentals
2.5K properties
Total number of reviews
1L reviews
Family-friendly rentals
1K properties are a good fit for families
Pet-friendly rentals
570 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
1.2K properties have a dedicated workspace
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- New Forest national park
- Bournemouth Beach
- Kimmeridge Bay
- Paultons Park Home of Peppa Pig World
- Oxford University
- Boscombe Beach
- Goodwood Motor Circuit
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Southbourne Beach
- Twickenham Stadium
- Chessington World of Adventures Resort
- West Wittering Beach
- Thorpe Park Resort
- Arundel Castle
- Highclere Castle
- RHS Garden Wisley
- Goodwood Racecourse
- Winchester Cathedral
- The Tank Museum
- Marwell Zoo
- Worthing Pier
- Highcliffe Beach
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