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The best vacation homes in Winchester

Check out our selection of great vacation homes in Winchester

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Millstream House, hotel in Winchester

Featuring a garden, Millstream House offers accommodations in Winchester. This property offers access to a terrace and free private parking.

It was clean and comfortable and spacious. It was a lovely place for the family to stay for the night. We all said it would have been better if we stayed in the future for longer, just so we could appreciate it more. The location was close to where we needed to go.
Scored 9.2
9.2
Rated wonderful
Wonderful
76 reviews
Price from
$204.78
1 night, 2 adults
The Post Barn, beautiful barn conversion 10mins from Winchester, hotel in Winchester

Providing a garden, The Post Barn, beautiful barn conversion 10mins from Winchester provides accommodations in Sparsholt. This property offers access to a terrace, free private parking, and free Wifi....

Scored 9.2
9.2
Rated wonderful
Wonderful
26 reviews
Price from
$174.06
1 night, 2 adults
The Stud House at Danebury, hotel in Winchester

Providing a garden, The Stud House at Danebury offers accommodations in Stockbridge. This vacation home provides free private parking, luggage storage space, and free Wifi.

Great place for our needs, peaceful and roomy. We were cycling the King Alfred's Way and it was particularly helpful the house had a washing machine for our kit. Could have stayed longer quite happily, whole group agreed it was our nicest stop of the tour.
Scored 9.2
9.2
Rated wonderful
Wonderful
6 reviews
Price from
$175.32
1 night, 2 adults
The Jockey's Lodge @ Danebury, hotel in Winchester

A recently renovated vacation home, The Jockey's Lodge @ Danebury offers accommodations in Stockbridge. This vacation home features free private parking, full-day security, and free Wifi.

Scored 9.5
9.5
Rated exceptional
Exceptional
21 reviews
Price from
$172.92
1 night, 2 adults
Forest Farm Barn Hampshire, hotel in Winchester

Forest Farm Barn Hampshire is located in Bishops Waltham, just 6.7 miles from Ageas Bowl and 11 miles from Southampton Guildhall.

Scored 9.0
9.0
Rated wonderful
Wonderful
5 reviews
Price from
$273.03
1 night, 2 adults
The Annexe @ Mandalay Lodge, hotel in Winchester

The Annexe @ Mandalay Lodge offers accommodations in Medstead, 5.2 miles from Jane Austen's House Museum and 16 miles from Frensham Great Pond and Common.

The Mandalay Lodge was absolutely beautiful, it's the perfect location for a getaway from the busy city. Johan was amazing and more than happy to help, he genuinely cares about you which was so lovely of him. I can't wait to book my next stay!!
Scored 9.6
9.6
Rated exceptional
Exceptional
34 reviews
Price from
$147.89
1 night, 2 adults
Cosy cabin in Annie’s meadow, hotel in Winchester

Cosy cabin in Annie’s meadow offers accommodations in West Meon, 10 miles from Jane Austen's House Museum and 16 miles from Ageas Bowl.

Scored 9.6
9.6
Rated exceptional
Exceptional
37 reviews
Price from
$227.53
1 night, 2 adults
The Barn, hotel in Winchester

Featuring a garden, The Barn offers accommodations in Romsey. This property offers access to a patio and free private parking.

Very welcoming and helpful hosts, very clean and comfortable place, very well equipped kitchen. It was nice to be able to sit on the terrace overlooking the front garden on the warm days.
Scored 9.7
9.7
Rated exceptional
Exceptional
95 reviews
Price from
$169.38
1 night, 2 adults
Mulberry Barn Annx - Self Contained Near Winchester, hotel in Winchester

Mulberry Barn Annx - Self Contained Near Winchester offers accommodations in Micheldever, 17 miles from Highclere Castle and 18 miles from Jane Austen's House Museum.

Perfect !
Scored 8.3
8.3
Rated very good
Very Good
63 reviews
Price from
$164.33
1 night, 2 adults
Accessible 3-bedroom bungalow with patio +driveway, hotel in Winchester

Featuring a garden, Accessible 3-bedroom bungalow with patio +driveway offers accommodations in Southampton. This property offers access to a patio, free private parking, and free Wifi.

Comfortably furnished. Plenty of room. Nice kitchen.
Scored 8.6
8.6
Rated excellent
Excellent
30 reviews
Price from
$213.88
1 night, 2 adults
All vacation homes in Winchester
Looking for a vacation home?
Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

Most booked vacation homes in Winchester this month

Enjoy breakfast in Winchester!

  • Stylish Stunning 2-BR Central Location, Sleeps 6, Winchester - By Blue Puffin Stays
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 6 reviews

    Stylish Stunning 2-BR Central Location, Sleeps 6, Winchester - By Blue Puffin Stays offers accommodations in Winchester, 13 miles from Southampton Guildhall and 13 miles from Southampton Cruise...

    This property was everything we hoped for and more! Comfortable beds, a fully stocked kitchen, and interiors that felt like home. Can’t wait to return

  • 2-BR Cosy Stunning Winchester Cottage Retreat with Garden, Near Cathedral! Sleeps 6, Pet Friendly with Parking - by Blue Puffin Stays
    Scored 9.9
    9.9
    Rated exceptional
    Exceptional
     · 7 reviews

    2-BR Cosy Stunning Winchester Cottage Retreat with Garden, Near Cathedral!

  • 4 Bed City House with Private Garden and Parking
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 34 reviews

    4 Bed City House with Private Garden and Parking offers accommodations in Winchester, 12 miles from The Mayflower Theatre and 12 miles from Southampton Guildhall.

    Great location. Close to the high street. Lovely property.

  • Sky View
    Breakfast options
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 44 reviews

    Sky View is located in Winchester, just 14 miles from Southampton Cruise Terminal and 16 miles from Ageas Bowl.

    Amazing spacious place! Very clean and easy check in.

  • No2 St Peters Street
    Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 14 reviews

    Featuring a garden, a bar, and free Wifi, No2 St Peters Street is a recently renovated vacation home 12 miles from The Mayflower Theatre and 12 miles from Southampton Guildhall.

    The decor was beautiful and done to a really high standard. Everything was spotless and the location was perfect!

  • The Nestle House
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 20 reviews

    Housed in a historic building, the recently renovated The Nestle House provides accommodations with a garden and free Wifi. A fitness room is available for guests.

    Great location, great host, anything you would need

  • Birdsong Rural Winchester Twyford - 2BR, 5BR, 7BR - sleeps upto 14
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 5 reviews

    Birdsong Rural Winchester Twyford - 2BR, 5BR, 7BR - sleeps upto 14 enjoys a location in Winchester, 7.6 miles from Ageas Bowl and 11 miles from The Mayflower Theatre.

  • Mallard Cottage
    Breakfast options
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 13 reviews

    Mallard Cottage is located in Winchester, just 13 miles from The Mayflower Theatre and 13 miles from Southampton Guildhall.

    The location was great, and off road parking was invaluable. The owners were very welcoming.

Save money on vacation homes in Winchester – budget options available!

  • Walsingham House - Peaceful Elevated - Near Oram's Arbour
    Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 27 reviews

    Walsingham House - Peaceful Elevated - Near Oram's Arbour is a recently renovated vacation home in Winchester where guests can make the most of the garden and barbecue facilities.

    It’s a wow property. Super clean. With all facilities

  • Designer's Town House
    Budget options available
    Scored 9.1
    9.1
    Rated wonderful
    Wonderful
     · 15 reviews

    Housed in a historic building, Designer's Town House offers accommodations with a garden and free Wifi in Winchester, 12 miles from The Mayflower Theatre.

    Superb location Great size Very well fitted & superb amenities

  • Hang Your Hat
    Budget options available
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 90 reviews

    13 miles from The Mayflower Theatre in Winchester, Hang Your Hat features accommodations with access to a steam room. This 5-star vacation home offers a garden.

    Home from home .Christmas tree was a lovely touch Would definitely recommend

  • South House
    Budget options available
    Scored 9.1
    9.1
    Rated wonderful
    Wonderful
     · 88 reviews

    South House offers accommodations in Winchester, 13 miles from The Mayflower Theatre and 14 miles from Southampton Guildhall.

    location was perfect for central town and cathedral

  • House in historic Winchester
    Scored 8.2
    8.2
    Rated very good
    Very Good
     · 8 reviews

    Housed in a historic building, House in historic Winchester features accommodations with a garden and free Wifi in Winchester, 14 miles from The Mayflower Theatre.

    Very clean, with everything we needed. Perfect location.

  • Hyde Brewery House - 2 bedroom house with parking
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 13 reviews

    Hyde Brewery House - 2 bedroom house with parking offers accommodations in Winchester, 14 miles from The Mayflower Theatre and 14 miles from Southampton Guildhall.

    clean, comfortable beds, warm and great well stocked kitchen

  • The Old Brewery Boardroom - Winchester City Centre - Unique Property - Free Parking - Sleeps 6 - by XPlus Stays
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 12 reviews

    Housed in a historic building, the recently renovated The Old Brewery Boardroom - Winchester City Centre - Unique Property - Free Parking - Sleeps 6 - by XPlus Stays offers accommodations with a...

    Great location for sightseeing. Beautiful interiors and good facilities.

  • Queens Road Rental - Winchester Accommodation
    Scored 8.2
    8.2
    Rated very good
    Very Good
     · 5 reviews

    13 miles from The Mayflower Theatre in Winchester, Queens Road Rental - Winchester Accommodation offers accommodations with access to a fitness room.

    Thank you, I had a very comfy and peaceful stay with everything I needed provided.

Great access to the city center! Check these vacation homes in Winchester

  • Kingsgate Cottage
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 2 reviews

    Providing a garden, Kingsgate Cottage offers accommodations in Winchester.

  • Piping Green 5 bedroom House
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Offering a garden, Piping Green 5 bedroom House provides accommodations in Winchester. Both free Wifi and parking on-site are available at the vacation home free of charge.

  • Millstream House
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 76 reviews

    Featuring a garden, Millstream House offers accommodations in Winchester. This property offers access to a terrace and free private parking.

    The property was beautiful in a beautiful location.

  • Beggar's Lane Cottage
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 60 reviews

    Housed in a historic building, Beggar's Lane Cottage features accommodations with a garden and free Wifi in Winchester, 13 miles from The Mayflower Theatre.

    Great location, close to town, bus routes and nature reserve.

  • Charming 4-Bed House in Winchester Free Parking
    Scored 7.5
    7.5
    Rated good
    Good
     · 4 reviews

    Charming 4-Bed House in Winchester Free Parking is located in Winchester, just 13 miles from The Mayflower Theatre and 13 miles from Southampton Guildhall.

  • The Old Sweet Shop
    Scored 7.0
    7.0
    Rated good
    Good
     · 1 review

    The Old Sweet Shop is located in Winchester, just 11 miles from Southampton Guildhall and 12 miles from Southampton Cruise Terminal. The 4-star vacation home is 11 miles from The Mayflower Theatre.

  • Charming Mews House in Historic Winchester

    Charming Mews House in Historic Winchester is located in Winchester, just 12 miles from The Mayflower Theatre and 12 miles from Southampton Guildhall.

  • Stylish 3BD Townhouse in Central Winchester

    Stylish 3BD Townhouse in Central Winchester is located in Winchester, just 13 miles from The Mayflower Theatre and 13 miles from Southampton Guildhall.

  • Winchester City House

    Winchester City House offers accommodations in Winchester, 13 miles from Southampton Guildhall and 14 miles from Southampton Cruise Terminal.

  • 59 Bar End Road

    59 Bar End Road is located in Winchester, just 12 miles from The Mayflower Theatre and 13 miles from Southampton Guildhall.

  • 4 Bed in Redlynch 82799

    4 Bed in Redlynch 82799 offers accommodations in Winchester, 12 miles from Salisbury Cathedral and 12 miles from Salisbury Train Station.

FAQ about vacation homes in Winchester

Vacation Homes That Guests Love in Winchester

  • Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 94 reviews
    Central location, wonderful room, excellent walk in shower, all very clean. Parking permit sorted by host prior to arrival. Very helpful host with plenty of local knowledge - gave us lots of extra ideas about places to explore. Made for great weekend break.
    Chris
    Young couple
  • Avg. price/night: $224.56
    Scored 8.1
    8.1
    Rated very good
    Very Good
     · 1,419 reviews
    Very clean, well appointed, excellent spa, friendly helpful staff.
    Yvette
    Solo traveler
  • Avg. price/night: $102.39
    Scored 7.1
    7.1
    Rated good
    Good
     · 3,413 reviews
    Location good for Winchester city and surrounding areas. Nice to have a swimming pool with a hotel. Room was large and cool. Beds very comfy. Towels nice white and fluffy. Bed linen very clean. Provided a upright fan. I had a settee in mine which made a change from lying on bed watching TV. Breakfast self service, but good selection of food
    Sally
    Solo traveler
  • Avg. price/night: $274.30
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 1,169 reviews
    The room was lovely, very clean and inviting. A fan was provided but it was an exceptionally hot day/night.Staff were approachable, friendly and happy to help.
    Fenella
    Young couple
  • Avg. price/night: $130.83
    Scored 7.7
    7.7
    Rated good
    Good
     · 1,325 reviews
    Beautiful hotel, very clean, excellent service by all members of staff.
    Carl
    Solo traveler
  • Scored 8.9
    8.9
    Rated excellent
    Excellent
     · 1,513 reviews
    Really quirky theme, lovely big bed, very clean
    Catherine
    Young couple
  • Scored 7.8
    7.8
    Rated good
    Good
     · 22 reviews
    Very central. Excellent location. Kitchen was VERY clean and bedrooms very comfortable.
    Helen
    Travelers with friends
  • Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 955 reviews
    The room was very clean and comfortable . We had evening meals as well as breakfast and the food was excellent . We stayed in Chisel room which had a balcony overlooking the beer garden .
    Michael
    Young couple
  • Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 13 reviews
    I have stay in a lot of holiday homes and one was by far the best. High spec and accommodating hosts.
    Brian
    Travelers with friends
  • Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 4 reviews
    Everything was wonderful. Feels like home, it was very clean and comfortable. Additionally the landlady was too sweet and caring. This holiday home is surely one of the best place to stay in Winchester. Will miss this place alot as it was such a beautiful place to stay. Thank you Miss.Lund for everything during our stay :)
    Evanglin
    Solo traveler

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