35 Best Vacation Rentals in Winchester - Holiday Lettings - Cabins

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37 Vacation rentals

(8) Excellent 

17

Vacation home rental

Hampshire / Winchester

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
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  …see more

from $223 / night

$1556 / week

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from $223 / night

(7) Very Good 

21

Cottage rental in Winchester

Twyford / Twyford

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
Dating from around 1450, Embessy Cottage is believed to be the oldest cottage in Twyford, Winchester Heavily beamed and filled with character and charm, the cottage is comfortably furnished, and enjoys a peaceful setting with a sheltered south facing garden. It  …see more

from $191 / night

$953 - $1010 / week

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from $191 / night

(4) Excellent 

27

Twyford Vacation cottage rental

Twyford / Twyford

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Private garden
Peacefully situated on a 4 acre smallholding in the depths of the Hampshire countryside, The Stables have been sensitively converted from an original farm building, once used to house shire horses, into exceptionally well thought-out accommodation, providing the perfect  …see more

from $124 / night

$530 - $888 / week

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from $124 / night

(15) Excellent 

27

Vacation cottage rental

Winchester / Pitt

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden
The Old Tractor Barn is one of 3 cottages within Crabwood Cottages. It is a fabulous holiday cottage set in farmland with wonderful views of horses grazing in rolling paddocks and chickens pecking around the old farmyard and direct access on to a bridleway.The location  …see more

from $121 / night

$616 - $1048 / week

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from $121 / night

(4) Very Good 

21

Vacation cottage in South East England

Hampshire / Winchester

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Private garden
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,  …see more

from $163 / night

$1137 / week

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from $163 / night

(4) Excellent 

11

South East England Vacation apartment rental

Hampshire / Winchester

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
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  …see more

from $197 / night

$1245 / week

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from $197 / night

(25) Very Good 

35

Vacation bungalow in South East England

Hampshire / Winchester

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
Luxury 4 Star self-catering holiday accommodation (now sleeps up to 6) comprising of 2 bedrooms and 2 bathrooms, lounge/diner and a fully fitted kitchen with integrated appliances: washing machine, dish washer, fridge, freezer, oven, hob, combi-microwave; lounge/diner;  …see more

from $153 / night

$1048 - $1798 / week

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from $153 / night

(8) Excellent 

15

South East England Vacation cottage accommodation

Hampshire / Winchester

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Private garden
Dating from the late 1800's and recently renovated The Down House Cottage nestles in the leafy village of Shawford, right on the edge of the National South Downs Park. Less than 3 miles from the historic heart of Winchester. The river Itchen flows through the village  …see more

from $108 / night

$756 / week

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from $108 / night

(4) Excellent 

24

South East England Vacation barn rental

Hampshire / Winchester

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Ask about children
  • Ask about pets
The Old Barns originally formed part of an old dairy farm and is surrounded by stunning English countryside. The barn conversion consists of 4 one bedroom holiday cottages all upside down accommodation taking advantage of the views of the Test Valley.Ideal  …see more

from $159 / night

$1016 - $1207 / week

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from $159 / night

(7) Excellent 

18

Log cabin rental in South East England

Hampshire / Winchester

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Suitable for children age 5+
  • Car not necessary
"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.  …see more

from $83 / night

$521 / week

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from $83 / night

(4) Excellent 

17

Vacation guest house in South East England

Hampshire / Winchester

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask about children
  • Ask about pets
The Hayloft is one of 3 cottages within Crabwood Cottages. It has been tastefully converted with fabulous views over rolling fields and forest, perfect for couples or overnight business trips. The Hayloft is situated right on a bridleway leading to wonderful woodland  …see more

from $121 / night

$616 / week

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from $121 / night

(24) Excellent 

8

Vacation apartment in South East England

Hampshire / Winchester

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
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 cent  …see more

from $134 / night

$839 - $978 / week

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from $134 / night

20

Vacation home in Kings Worthy

Winchester / Kings Worthy

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
Eversley Cottage Annex is a beautiful 3 bedroom cottage which is located at the gateway to the South Downs National Park and within 2 1/2 miles from Winchester Historic City Centre, 30 minutes from Stonehenge, Salisbury and 55 minutes by train to the centre of London  …see more

from $166 / night

$1042 - $1207 / week

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from $166 / night

(16) Excellent 

16

Vacation penthouse rental

Hampshire / Winchester

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Car not necessary
Rated Four Stars by the AA, and newly on the market mid September 2014 ! Be one of the first to stay!!'Sky' is an exciting Grade II listed roof-top 'boutique' style penthouse apartment, with parking in the centre of historic Winchester. Perched on the top of a Georgian  …see more

from $229 / night

$1524 - $1626 / week

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from $229 / night

7

Vacation home in South East England

Hampshire / Winchester

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
DETAILS FOR NO. 12 ST CLEMENT STEET Holiday Cottage in Winchester UK at No. 12 St Clement Street "Honeysuckle". A delightful period cottage believed to date back to the 1800's, located in the heart of the City and within walking distance of the High Street and mainline  …see more

from $188 / night

$1310 - $1372 / week

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from $188 / night

(10) Very Good 

19

Vacation apartment with golf nearby in South East England

Hampshire / Winchester

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Car not necessary
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 p  …see more

from $140 / night

$826 / week

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from $140 / night

(2) Very Good 

18

Home rental in South East England

Hampshire / Winchester

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Car not necessary
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 secur  …see more

from $191 / night

$1207 - $1829 / week

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from $191 / night

29

Vacation townhouse in South East England

Hampshire / Winchester

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Private garden
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 und  …see more

from $215 / night

$1502 - $1564 / week

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from $215 / night

(2) Excellent 

14

Vacation home in South East England

Hampshire / Winchester

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
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  …see more

from $190 / night

$1325 / week

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from $190 / night

7

South East England Vacation home rental

Hampshire / Winchester

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
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 ha  …see more

from $889 / night

$2921 / week

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from $889 / night

7

Vacation apartment in South East England

Hampshire / Winchester

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
This distinctive period house dates back to circa 1900 when it was originally the front office of the Winchester Brewery. The property has since been sympathetically converted to provide a wonderful house which has retained some lovely period features, including wood pa  …see more

from $223 / night

$1556 / week

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from $223 / night

11

Vacation home in South East England

Hampshire / Winchester

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
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 thr  …see more

from $236 / night

$1650 - $1837 / week

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from $236 / night

20

Vacation shepherds hut in South East England

Hampshire / Winchester

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
Rent this beautiful shepherds hut set in a idyllic location of a private four acre field with access to a its own woodlands. Discover and enjoy the natural wildlife that surrounds the hut including an active badger set, rabbits, hares, pheasant and wild deer or spot  …see more

from $83 / night

$508 / week

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from $83 / night

(3) Excellent 

9

South East England Vacation b&b rental

Hampshire / Winchester

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Ask about pets
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 o  …see more

from $83 / night

$578 / week

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from $83 / night

7

Vacation b&b in South East England

Hampshire / Winchester

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
The rooms are fitted with a flat-screen TV and DVD player. You will find a coffee machine in the room. Every room is fitted with a private bathroom. For your comfort, you will find free toiletries and a hairdryer. Winchester Crown Court is 400 metres from Saskia's B&B  …see more

from $121 / night

$845 / week

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from $121 / night

14

Vacation lodge rental

Hampshire / Winchester

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The Old Orchard is one of 3 accommodations within Crabwood Cottages. It is a peaceful rural holiday accommodation with lovely views and wonderful forest walks on your doorstep, yet perfectly located to explore The South of England and nearby cathedral city of Winchester  …see more

from $153 / night

$889 - $4877 / week

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from $153 / night

9

Vacation home rental

Hampshire / Winchester

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
DETAILS NO. 73 TOWER STREET Holiday Home in Winchester UK at No. 73 Tower Street No. 73 Tower Street has a really great city centre location as holiday home in Winchester because it is situated within a few minutes walk of the Railway Station, Discovery Centre, Theatre  …see more

from $236 / night

$1650 - $1712 / week

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from $236 / night

(14) Excellent 

8

Vacation home in South East England

Hampshire / Winchester

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
Prices for a single room start from £95 Prices for the whole house start from £335 two bare feet Winchester offers loft-style living to those looking for a break with friends and family or to those travelling with work. Each of the 3 individually styled bedrooms have  …see more

from $426 / night

$2979 / week

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from $426 / night

6

Vacation b&b in South East England

Hampshire / Winchester

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
The rooms are fitted with a flat-screen TV and DVD player. You will find a coffee machine in the room. Every room is fitted with a private bathroom. For your comfort, you will find free toiletries and a hairdryer. Winchester Crown Court is 400 metres from Saskia's B&B,  …see more

from $115 / night

$801 / week

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from $115 / night

44

Hampshire / Winchester

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary

 …see more

from $153 / night

$1048 - $1798 / week

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from $153 / night

(1) Excellent 

21

Hampshire / Winchester

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly

 …see more

from $210 / night

$1397 / week

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from $210 / night

33

Vacation home rental

Hampshire / Winchester

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
DETAILS NO. 02 BECKS MEWS No. 02 Becks Mews - Sleeping 4-7 people is a modern mews house perfectly placed self catering accommodation within minutes walk of the station. The bespoke doors, leaded dormers and the appearance of the house is smart, attractive and appropr  …see more

from $254 / night

$1773 - $1960 / week

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from $254 / night

17

Vacation apartment in South East England

Hampshire / Winchester

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
DETAILS NO. 01B 1 CLIFTON TERRACE Holiday Apartment in Winchester UK at No. 01B 1 Clifton Terrace. No. 01B 1 Clifton Terrace is a light and attractive 1st floor apartment situated in the heart of central Winchester in a popular and elevated residential area immediatel  …see more

from $202 / night

$1413 - $1537 / week

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from $202 / night

47

Vacation apartment in South East England

Hampshire / Winchester

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Situated within a former warehouse building converted in 1973, this serviced apartment offers great accommodation for 4 on the 2nd floor (with lift) and is surprisingly quiet for the heart of the City. FACILITIES NO. 11 COSSACK LANE HOUSE Apartment located on the 2nd fl  …see more

from $157 / night

$1094 / week

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from $157 / night

(28) Excellent 

8

Hampshire / Winchester

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Private garden

 …see more

from $185 / night

$953 - $1696 / week

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from $185 / night

(6) Very Good 

11

Hampshire / Winchester

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 45 mi
  • Car not necessary
  • Air conditioning

 …see more

from $115 / night

$889 / week

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from $115 / night

10

Winchester / Kings Worthy

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Pet friendly

 …see more

from $115 / night

$801 / week

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from $115 / night