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Winchester Family & Kid Friendly Rentals

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    Travelers to Winchester are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    27 Matching Rentals in WinchesterView all 36 rentals
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    The Old Tractor Barn, Crabwood Cottages1 / 31
    (21)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Willow Cottage - The Old Barns1 / 41
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    The Granary Annex at Worthy Barn1 / 14
    (11)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Parking
    • Balcony
    • Central Heating
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 7, 2018
    Had a wonderful stay at the annex was very nice and cosy. The farm shop over the road was lovely. We was lucky enough to have some really good weather to visit Portsmouth...
    Reviewed May 29, 2018
    An ideal resting place, tastefully furnished and nestling amongst watercress fields. An ideal size for a married couple and adult daughter whilst we attended a wedding locally...
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    About this property
    Ideal location for visiting the beautiful & historic Winchester or Hampshire, the Granary is 2 miles from Winchester, opposite a farm shop & lovely country pub is a 10 minute walk away. The main bedroom has a kingsize bed and views across watercress beds, the adjoining bedroom has bunk beds. Open...
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    Winchester, Hampshire SO23 7LD
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South House - In the centre of Winchester1 / 21
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Central Heating
    • Wi-Fi
    • Terrace
    • DVD Player
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 25, 2017
    Loved our stay at South House! We walked to sights, restaurants, pubs, etc., and the house was clean and tidy. We appreciated the games since it's poured down rain one night...
    Reviewed January 18, 2017
    We had a fabulous stay at the South House in Winchester. Booking was easy, great communication from the owners. The location of the place is perfect - 2 minutes from the centre...
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    About this property
    South House is a beautiful 3 bedroom home situated in the heart of Winchester. Its elegant contemporary design makes it a unique and a very comfortable place to stay in this historic city. All the main cultural attractions including Winchester Cathedral, and the Great Hall displaying the famous...
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    Winchester, Hampshire SO23 8DB
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB1 / 21
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Terrace
    • Housekeeping Included
    • DVD Player
    • Balcony
    • Washer
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 5, 2018
    Booked a two night mid week stay for a family of four and a dog. Lodge is of good quality on a well kept site, very spacious and clean. Wouldn’t recommend booking through...
    Reviewed April 23, 2018
    What can be said about south Winchester golf lodges. Well firstly I would like to thank all the staff including Yvonne / Emma & Lawrence for a great service from start to...
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    About this property
    SHORT BREAKS - 2 night min stay required (no check in available Sunday) Beautiful vaulted ceilings and exposed wood provides a tranquil and relaxing setting. Fully equipped kitchen and open plan living and dinning area with cosy fire place, TV, DVD player and sound system all furnished to 5 star...
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    Winchester, Hampshire SO22 5SW
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Loft Winchester1 / 11
    (7)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Central Heating
    • Wi-Fi
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 13, 2018
    Spacious accommodation situated within pleasant strolling distance of Winchester city centre. A thoroughly enjoyable short break exploring the historic buildings, pubs and...
    Reviewed July 31, 2018
    Stayed here with 2 sisters for a city break during a very hot spell of weather. The bedrooms were well presented and the bedding of good quality, though the second and third...
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    About this property
    Positioned across the road from Oram's Arbour park, and just a 5 minute walk from town and the station, this 3 bedroom apartment has just been refurbished,creating a contemporary, light and airy space.It occupies the two top floors of a victorian house and is over 1000q ft. The master bedroom has...
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    Winchester, Hampshire SO225BU
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Housekeeping Included
    • Wi-Fi
    • Central Heating
    • DVD Player
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stylish and very well presented town-house is within walking distance of Winchester town centre and its wonderful amenities. The property benefits from a courtyard garden, roof terraces, balcony and secure under croft allocated parking. At street level there is under croft gated parking with...
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    Winchester, Hampshire SO23 0AD
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Garden Apartment in Winchester1 / 16
    (18)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Central Heating
    • Wi-Fi
    • Shared Yard
    • Washer
    • Terrace
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    The Garden Apartment was handy to both the train station and High Street, and we found Winchester to be a lovely city in which to base ourselves on our holiday. Two small...
    Reviewed 4 weeks ago
    This apartment has all you need for a excellent base to launch you daily excursions from. Within walking distance of all of Winchester's main historical attractions, pubs...
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    About this property
    The Garden apartment, newly completed in Summer 2011 is quietly located in the City Centre, with comfortable, comtemporary stylish furnishings. This self catering apartment is very quiet, with no road noise. There is a large bedroom with lovely vaulted ceiling and patio windows looking into the...
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    Winchester, Hampshire SO23 8DJ
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Idyllic Hampshire Hideaway - The Orchard Studio1 / 9
    (11)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Terrace
    • Patio
    • DVD Player
    • Balcony
    • Wi-Fi
    • Private Yard
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 22, 2018
    A fantastic stay. A welcoming and serene location, accompanied by the silent majesty of huge rustling trees and a very green vantage point, this is the ideal place from which to...
    Reviewed August 13, 2018
    The most beautiful little secret hideaway in a totally peaceful setting. A real escape from the rat race. Victoria was super friendly and breakfast was fantastic. We will...
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    About this property
    The Orchard Studio is an idyllic self contained hideaway, tucked in a corner of our truly English country garden. It is completely private and the perfect place to relax and unwind. We offer a warm welcome, comfortable bed and delicious breakfast. The cathedral city of Winchester is only three...
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    Location Information
    Winchester, Hampshire SO21 2PA
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Stylish House in Winchester1 / 17
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Secure Parking
    • Washer
    • DVD Player
    • Wi-Fi
    • Shared Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 5, 2018
    This property is an excellent house for anyone wanting a place to stay while touring the South of England or staying in Winchester. It is centrally located out of the downtown...
    Reviewed September 17, 2018
    Modern, smart house in a leafy suburb. Approx. 20 minute walk into Winchester, a very old city with an eventful past. There are many historical buildings to visit.
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    About this property
    The Pavilion is a stunning contemporary detached house in the centre of Historic Winchester, and offers a stylish blend of ultra modern features and spacious accommodation. There are two bedrooms, one with ensuite bathroom, these have glazed doors leading to a secure enclosed courtyard area, there...
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    Location Information
    Winchester, Hampshire SO23 8DJ
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Self Contained Garden Annexe1 / 18
    (14)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • Shared Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 29, 2018
    I stayed in the Garden Annexe for 3 nights and had a wonderful stay. The design of the house is inspiring and unique. It was cozy, well equipped and conveniently situated in...
    Reviewed August 19, 2018
    We spent a very relaxed few days at the Armadilla. It was cosy and well laid out. The perfect base for exploring Winchester. The hosts were helpful without being imposing and...
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    About this property
    'Winchester Garden Annexe' Beautiful, self contained, wood clad cabin. Rustic, boat like appearance from the outside. Clean modern appearance inside with all you need for a pleasant, comfortable stay. A wonderfully unique, self contained wood clad cabin in our garden. Known as an 'Armadilla' it is...
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    Winchester, Hampshire SO22 6HN
    Cabin - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Luxury 2 Bedroom Scandinavian Lodge with HOT TUB1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Housekeeping Included
    • Grill
    • Balcony
    • Washer
    • Wi-Fi
    • Hot Tub
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 12, 2018
    Our family enjoyed the luxury and beauty of our lodge and the hot tub was a real bonus. It was a rainy weekend, but we even really enjoyed the putting green. Thanks
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    About this property
    SHORT BREAKS - 2 night min stay required (no check in available Sunday) Beautiful vaulted ceilings and exposed wood provides a tranquil and relaxing setting. Fully equipped kitchen and open plan living and dinning area with cosy fire place, TV, DVD player and sound system all furnished to 5 star...
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    Winchester, Hampshire SO22 5SW
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Housekeeping Included
    • DVD Player
    • Washer
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DETAILS NO. 79 TOWER STREET Holiday Home in Winchester UK is charming period property with a City Centre location making it an ideal holiday home. You and your family can enjoy this holiday home in Winchester and all the city centre has to offer being just a stone's throw away. Two double bedrooms,...
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    Location Information
    Winchester, Hampshire SO23 8TA
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Cosy character cottage in central Winchester1 / 18
    (11)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • Terrace
    • Wi-Fi
    • Washer
    • Grill
    • DVD Player
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 6, 2018
    Well located between major highways and downtown Winchester. Quiet 1-way street, good parallel parking, Just down to the corner and right for many restaurants and stores...
    Reviewed December 11, 2017
    The Cosy Cottage’s location is perfect for accessing the delightful city of Winchester. We did not have a car and were able to walk to local historic sights, wonderful...
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    About this property
    Charming period cottage quietly situated in one on Winchester's quaint old streets. This renovated cottage still retains the old features which give it plenty of character - old fireplaces and doors and twisty old staircase. It is ideally situated in the city centre, so all the historic sites,...
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    Winchester, Hampshire SO23 0HF
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Private Yard
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This enchanting terraced holiday cottage is a short stroll from the town's historic high street which provides an abundance of boutiques, pubs and restaurants. Inside the cottage you will be able to relax into a spacious entertaining space spread across the ground floor. An extending dining table...
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    Winchester, Hampshire SO24 9JH
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury 3 bedroom Scandinavian Lodge1 / 20
    (9)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
    • Cable/satellite TV
    • Central Heating
    • DVD Player
    • Grill
    • Washer
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 24, 2016
    We loved the lodge and the hot tub. the welcome basket with local bacon and free range eggs was lovely. We couldn't fault the place. We will definitely go back. Nothing much...
    Reviewed October 23, 2015
    We booked the 3-bed, 2-bath lodge for a Mon-Fri break with friends. Accommodation was clean and functional, the open area of kitchen, dining table and lounge was ideal for...
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    About this property
    SHORT BREAKS - 2 night min stay required (no check in available Sunday) Beautiful vaulted ceilings and exposed wood provides a tranquil and relaxing setting. Fully equipped kitchen and open plan living and dinning area with cosy fire place, TV, DVD player and sound system all furnished to 5 star...
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    Location Information
    Winchester, Hampshire SO22 5SW
    Cabin - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunnyside1 / 7
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 17, 2018
    We have had a really lovely stay in this excellent apartment. The decor is fab and well thought out with lots of lovely little touches, and a very comfy bed. It is well...
    Reviewed June 13, 2018
    Lovely spacious comfortable accommodation ideal for exploring nearby Winchester and lovely surroundings
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    About this property
    Stunning apartment with parking in a beautiful location. The apartment has a full functioning kitchen with a dinning area. The Lounge is a sun room with a lot of natural light. The apartment is 1 min away from the bus stop and there is a bus every 15 mins into Winchester. Winchetser is 5 mins...
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    Winchester, Hampshire SO23 7QU
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    South House Winchester1 / 17
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Parking
    • Central Heating
    • Balcony
    • Washer
    • DVD Player
    • Terrace
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 8, 2017
    The location is good within walking distance of Winchester town, rooms were spacious, only one bedroom with on-suite though other two rooms shared a bathroom. Car parking was a...
    Reviewed November 23, 2016
    We really enjoyed our break in this modern well kept house. We all felt at home immediately, especially my 3 year old son who is often fussy about being away from what is...
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    About this property
    South House is a beautiful 3 bedroom home situated in the heart of Winchester. Its elegant contemporary design makes it a unique and a very comfortable place to stay in this historic city. All the main cultural attractions including Winchester Cathedral, and the Great Hall displaying the famous...
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    Winchester, Hampshire SO23 8DB
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Luxury 2 Bedroom Scandinavian Lodge1 / 13
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
    • Balcony
    • Washer
    • Grill
    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 4, 2015
    Some friends and I stayed here for 3 nights as part of a reunion. it was brilliant, the cabins are really well built and looked after. They are warm and comfortable, especially...
    Reviewed July 2, 2015
    Hi I just spent 7 days at these lodges and they are a cut above the normal caravan ,chalet type accommodations. They are not the cheapest but I was impressed with the finish and...
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    About this property
    SHORT BREAKS - 2 night min stay required (no check in available Sunday) Beautiful vaulted ceilings and exposed wood provides a tranquil and relaxing setting. Fully equipped kitchen and open plan living and dinning area with cosy fire place, TV, DVD player and sound system all furnished to 5 star...
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    Location Information
    Winchester, Hampshire SO22 5SW
    Cabin - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    This first floor apartment is set within an historic Grade II listed mill on the banks of the River Itchen; the building itself was used during filming of a scene from the film ‘Brief Encounter' in the 1970s with Richard Burton and Sophia Loren! Step into the spacious entrance hall today and...
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    Winchester, Hampshire SO23 9NJ
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • DVD Player
    • Internet Access
    • Terrace
    • Patio
    • Parking
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Riverside Cottage is away from the maddening crowd yet easy access to Winchester, Andover, London with lots of local interest too It is an old thatched cottage set in 8 acres and on the River Dever. It overlooks fields and so private and relaxing. Riverside also have a lodge for extra guests...
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    Winchester, Hampshire SO21 3QJ
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    This contemporary styled and renovated period terraced cottage provides guests a very comfortable stay in the heart of one of the most historic streets in Winchester. Located on the Jane Austen walking Tour route, this property is set in the picturesque Kingsgate Village and makes you feel like...
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    Location Information
    Winchester, Hampshire SO23 9JW
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    Dashwood Terrace is a recently upgraded quintessential terraced house, just a few minutes walk from the city and close to St Giles Hill which offers stunning views across the ancient capital of England. Located towards the end of a no through road, it is a quiet and family friendly location that...
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    Location Information
    Winchester, Hampshire SO23 0HQ
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    1 Abbotts Court Mews1 / 8
    (29)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Terrace
    • Balcony
    • Wi-Fi
    • Parking
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 22, 2018
    The apartment is well equiped, it is not so big but everything you need is present. Except a coffee machine.It is very nice that the main bedroom has an airconditioning system...
    Reviewed August 13, 2018
    This apartment is situated close enough to the station with a few pubs along the way (which suited us just fine).Its in a quiet and picturesque area. Perfect for weekend...
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    About this property
    1 Abbotts Court Mews is a two bedroom luxury apartment which can accommodate up to five people. This architect designed property, built in 2005, uniquely provides a detached first floor apartment conveniently tucked away in a secluded location yet close to the city centre. Located within the...
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    Location Information
    Winchester, Hampshire SO23 7BE
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedroom, Luxury Scandinavian Lodge, set in woodland1 / 12
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Balcony
    • DVD Player
    • Patio
    • Wi-Fi
    • Washer
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 28, 2018
    We had a wonderful stay at the South Winchester Lodges...It was perfect for our getaway weekend! The lodge itself was very spacious, clean and had everything we required! The...
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    About this property
    A beautiful 3 bedroom, 2 bathroom Scandinavian Lodge (sleeps 6) set in the heart of South Winchester Golf Course just 3 miles from Winchester city centre and with great transport links to the south coat, London and the M3 corridor. Whether you are relocating to the area, carrying out home...
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    Winchester, Hampshire SO22 5SW
    Cabin - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • DVD Player
    • Parking
    • Balcony
    • Washer
    • Central Heating
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful 2 bedroom, 2 bathroom Scandinavian Lodge (sleeps 4) set in the heart of South Winchester Golf Course just 3 miles from Winchester city centre and with great transport links to the south coat, London and the M3 corridor. Whether you are relocating to the area, carrying out home...
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    Location Information
    Winchester, Hampshire SO22 5SW
    Cabin - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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