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The best cottages in Winchester

Check out our selection of great cottages 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.

Beautiful home close to town center.
Scored 9.2
9.2
Rated wonderful
Wonderful
64 reviews
Price from
$234.26
per night
Lane End Cottage, hotel in Winchester

Providing a garden, Lane End Cottage provides accommodations in Ovington. This property offers access to a terrace, free private parking, and free Wifi.

The quiet and privacy. The comfort
Scored 9.6
9.6
Rated exceptional
Exceptional
67 reviews
Price from
$247.28
per night
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
22 reviews
Price from
$168.67
per night
Woodlands Cottage Farm, hotel in Winchester

Providing a garden, Woodlands Cottage Farm features accommodations in Wickham. With garden views, this accommodation offers a terrace.

everything
Scored 9.7
9.7
Rated exceptional
Exceptional
162 reviews
Price from
$182.20
per night
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 9.5
9.5
Rated exceptional
Exceptional
28 reviews
Price from
$152.27
per night
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
35 reviews
Price from
$227.75
per night
3 Bedrooms house ideal for long Stays!, hotel in Winchester

3 Bedrooms house ideal for long Stays! offers accommodations in Southampton, 3.1 miles from Ageas Bowl and 3.2 miles from The Mayflower Theatre.

Scored 9.4
9.4
Rated wonderful
Wonderful
26 reviews
Price from
$184.81
per night
Mulberry Barn Annx - Self Contained Near Winchester, hotel in Winchester

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

Perfect !
Scored 8.4
8.4
Rated very good
Very Good
64 reviews
Price from
$169.19
per night
The Paddock View at Danebury, hotel in Winchester

The Paddock View at Danebury offers accommodations in Stockbridge, 13 miles from Old Sarum and 14 miles from Salisbury Train Station.

Scored 8.3
8.3
Rated very good
Very Good
12 reviews
Price from
$101.55
per night
Luxury modern 1 bedroom house, hotel in Winchester

Luxury modern 1 bedroom house in Southampton provides accommodations with free Wifi, a 7-minute walk from Southampton Guildhall, 1.4 miles from Southampton Cruise Terminal, and 4.6 miles from Ageas...

N/A
Scored 8.1
8.1
Rated very good
Very Good
16 reviews
Price from
$96.98
per night
All cottages in Winchester
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Cottages are perfect for travelers who enjoy feeling cozy and independent in the countryside. Usually small, traditionally built houses, cottages are spread across one or two floors – making them great for families or vacations with a little more privacy.
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Most booked cottages in Winchester this month

Enjoy breakfast in Winchester!

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

    Stylish 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 Terminal.

    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 Bed Cosy 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 Bed Cosy Winchester Cottage Retreat with Garden, Near Cathedral! Sleeps 6, Pet Friendly with Parking - by Blue Puffin Stays is located in Winchester, just 13 miles from The Mayflower Theatre and 13...

  • Millstream House
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 64 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.

  • 4 Bed City House with Private Garden and Parking
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 32 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.

  • House situated on River Itchen
    Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 34 reviews

    House situated on River Itchen is located in Winchester, just 16 miles from Ageas Bowl and 16 miles from Jane Austen's House Museum.

    Immaculate. Could not have wished for more from a property rental.

  • Beautiful house on the River Itchen
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 36 reviews

    Housed in a historic building, Beautiful house on the River Itchen features accommodations with a garden and free Wifi in Winchester, 13 miles from The Mayflower Theatre.

    Lovely clean house with everything you need. Excellent location.

  • Sky View
    Breakfast options
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 40 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
     · 13 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!

These cottages in Winchester have options with FREE cancellation

  • The Nestle House
    Free cancellation options available
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 17 reviews

    14 miles from Southampton Cruise Terminal in Winchester, The Nestle House offers accommodations with access to a fitness room.

    The attention to detail was exceptional from the host.

  • Birdsong Rural Winchester Twyford - 2BR, 5BR, 7BR - sleeps upto 16
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 5 reviews

    Birdsong Rural Winchester Twyford - 2BR, 5BR, 7BR - sleeps upto 16 enjoys a location in Winchester, 7.6 miles from Ageas Bowl and 11 miles from The Mayflower Theatre.

  • Mallard Cottage
    Free cancellation options available
    Scored 9.9
    9.9
    Rated exceptional
    Exceptional
     · 10 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.

  • Queens Road Rental - Winchester Accommodation
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 5 reviews

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

    The location was excellent. The property was clean and tidy and a small provisions pack made available.

  • Walsingham House - Peaceful Elevated - Near Oram's Arbour
    Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 28 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
    Free cancellation options available
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 13 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
    Free cancellation options available
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 91 reviews

    Set in a former Brewery workers cottage built by Lord Northbrook in 1843, Hang Your Hat is located in Winchester and offers accommodations with a private courtyard garden, free WiFi and a log...

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

  • South House
    Free cancellation options available
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 90 reviews

    South House is located in Winchester, on the border of the scenic South Downs National Park. Free WiFi access is available in this holiday home.

    location was perfect for central town and cathedral

Traveling by car? These cottages in Winchester offer free parking!

  • Hyde Brewery House - 2 bedroom house with parking
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 10 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.

    Great property but v admin happy. Huge deposit required. Didn’t see or speak to anyone. No toilet roll or salt n pepper

  • The Old Brewery Boardroom - Winchester City Centre, Free Parking for 2 Cars, Sleeps 6
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 10 reviews

    Housed in a historic building, the recently renovated The Old Brewery Boardroom - Winchester City Centre, Free Parking for 2 Cars, Sleeps 6 offers accommodations with a garden and free Wifi.

    Great location for sightseeing. Beautiful interiors and good facilities.

  • Pemberly
    Free parking
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 7 reviews

    Pemberly offers accommodations in Winchester, 15 miles from Ageas Bowl and 18 miles from Jane Austen's House Museum.

    Great location and surprisingly quiet nights sleep

  • Beggar's Lane Cottage
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 62 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.

  • Stylish 3BD Townhouse in Central Winchester

    Stylish 3BD Townhouse in Central Winchester offers accommodations in Winchester, 13 miles from The Mayflower Theatre and 13 miles from Southampton Guildhall.

  • Kingsgate Cottage

    Providing a garden, Kingsgate Cottage offers accommodations in Winchester.

  • 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.

  • 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.

FAQ about cottages in Winchester

Cottages That Guests Love in Winchester

  • Avg. price/night: $206.93
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 432 reviews
    Period hotel beautifully modernised in charming location. The staff were so helpful and lovely without exception. We enjoyed drinks on the terrace, and a good quality 3-course dinner in the light and airy ‘new’ dining room. Comfortable room with very sweet attention to detail, lovely toiletries. Breakfast in the cosy ‘old’ dining room was exceptional. Hope to stay longer when we come again.
    Catherine
    Young couple
  • Avg. price/night: $141.73
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 966 reviews
    Lovely stay for a night in the Plough. Charming place, cosy bedroom, large selection of beers for those who want to end the day with a pint (or start it), quiet even if along the road and a very nice staff ! Also breakfast was super !
    Victor
    Young couple
  • Avg. price/night: $206.93
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 432 reviews
    The Fox, formerly The Fox and the Hound has been renovated. It offers everything to make a traveler happy in the tiny hamlet of Crawley (the pretty Crawley with thatched cottages, not the Crawley near London Gatwick).
    Hilary
    Young couple
  • Avg. price/night: $147.06
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 1,251 reviews
    Our third stay at this hotel which says it all. The staff are brilliant as are the room amenities. Great countryside location and handy for stopping after coming from the ferry in Portsmouth. Great outdoor seating areas as well as a nice cosy, friendly bar area in the main pub.
    susan
    Young couple
  • Avg. price/night: $156.17
    Scored 8.9
    8.9
    Rated excellent
    Excellent
     · 77 reviews
    The atmosphere was welcoming & warm. David was friendly, funny, made you feel at home straight away. The accommodation was beautifully cosy cottage chic, the beds were comfy, the bedding clean & crisp white & nice & cool with the lovely wooden blinds. The food is 5* excellent with large portions for the bigger appetites in the family. The staff are friendly & knowledgeable & we will definitely stay there again.
    T
    Tracy
    Family with young children
  • Avg. price/night: $520.58
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 249 reviews
    Beautiful property in a stunning setting. We went for our anniversary. Staff were exceptionally good. Really attentive and professional and helpful. We had a small issue at breakfast and they were very apologetic and kind. Facilities were amazing and room super comfortable and romantic. We had an afternoon tea which was delicious and they took great care of our dietary requirements. Lovely grounds for walks and cosy drawing room to spend an evening reading or chatting with loved ones. Had the best time and wholeheartedly recommend!!
    AALIYA
    Young couple
  • Scored 9.3
    9.3
    Rated wonderful
    Wonderful
     · 92 reviews
    The staff were amazing. Went beyond the call of duty to help me with a flat tyre and saved my skin. Nothing was too much for them. Also idyllic setting with lots of animals. Horses, llamas, baby donkeys, friendly goats, geese and lots of wild baby bunny rabbits. Well located for Mottisfont and also Winchester. Se in amazing countryside with lots of beautiful historic cottages and streams. I hear you can even go wild swimming.
    Sally-Ann
    Young couple
  • Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 91 reviews
    Lovely cottage very close to the centre of Winchester. A cosy place in a quiet street with a well equipped kitchen and decent sized rooms.
    Mark
    Young couple
  • Scored 9.3
    9.3
    Rated wonderful
    Wonderful
     · 256 reviews
    We had a very comfortable and happy stay! The property is very spacious and clean. The pictures online do not do justice. The lodge is gorgeous and very cozy. We had an amazing time at the hot tub as well.
    A
    Anonymous
    Family with young children
  • Avg. price/night: $147.06
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 1,251 reviews
    Room was super clean spacious and well equipped with towels, Wi-Fi connection. Fresh and clean linen. Extremely friendly staff. Food was delicious. Breakfast was excellent. Surrounding countryside was charming and the whole venue very cozy.
    Charles
    Young couple

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