Winchester vacation rentals

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Top-rated vacation rentals in Winchester

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Guesthouse in Winchester

4.95 out of 5 average rating, 260 reviews

Water Meadows Lodge beside Winchester South Downs

"Riverside" Garden Lodge is separate, secure and sunny with a private garden and free parking in St Cross village Winchester, beside the Water Meadows and South Downs. Only 15 minutes walk from the centre via the famous Water Meadow paths or road's celebrated inns you have an ideal location to enjoy this historic city. Finished to high standards, the double bedroom, spacious living / dining room, kitchen, shower / loo have the essential luxuries. Plus Fast WiFi, 42" Smart TV and Laundry service.

Aug 18 – 25

R2,550 ZAR per night
Guest favorite

Farm stay in Headbourne Worthy

5.0 out of 5 average rating, 228 reviews

A Unique Farm Retreat

There’s something magical about The Granary. Set in acres of farmland with spectacular sunrises and sunsets, The Granary brims with rustic charm. A dreamy hideaway with an outdoor copper bath and wood fired hot tub. An idyllic get-away-from-it-all yet only 3 miles to historic Winchester. Soak amid hot water, steam and fresh air surrounded by nature and birdsong, enjoy magnificent sunsets from the ‘Sundowner’ or cosy up toasting marshmallows over the fire pit - a perfect escape to unwind.

Feb 7 – 14

R4,045 ZAR per night
Guest favorite

Apartment in Hampshire

4.95 out of 5 average rating, 171 reviews

Romantic, artist’s flat, superb central location.

Romantic, bow-fronted, ground floor Regency property with lots of character. Well-appointed but down to earth. Directly opposite the famous King Alfred's statue in the centre of town: 1 minute walk to the river, 1 minute to city centre shops, 3 mins to Winchester Cathedral, 15 mins to train station. Kitchen opens into small pretty garden, then onto quiet cul-de sac for parking (permit provided- parking in the cul-de-sac not guaranteed but there are plenty of streets within the permit zones).

Jun 17 – 24

R3,121 ZAR per night

Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

The Great Hall55 locals recommend
Winchester Christmas Market11 locals recommend
Sainsbury's7 locals recommend
St Catherine's Hill55 locals recommend
Theatre Royal Winchester41 locals recommend
The Old Vine21 locals recommend

Other great vacation rentals in Winchester

Guest favorite

Hut in Winchester

4.97 out of 5 average rating, 454 reviews

The Pigsty

Aug 7 – 14

R4,374 ZAR per night
Guest favorite

Cottage in Hampshire

5.0 out of 5 average rating, 170 reviews

Cosy country cottage with chalk stream charm

May 10 – 17

R3,328 ZAR per night
Guest favorite

Home in Otterbourne

4.98 out of 5 average rating, 121 reviews

Quiet semi-detached house near Winchester

May 4 – 11

R2,097 ZAR per night
Guest favorite

Loft in Charlecote

4.92 out of 5 average rating, 158 reviews

Beautiful Apartment in Centre of Winchester

Apr 2 – 9

R3,088 ZAR per night
Guest favorite

Guesthouse in Hampshire

4.9 out of 5 average rating, 304 reviews

Cosy Annexe in a beautiful part of Winchester

Apr 30 – May 7

R1,781 ZAR per night
Guest favorite

Shepherd’s hut in Winchester

4.96 out of 5 average rating, 325 reviews

Shepherd's Hut with Hot Tub near Winchester

Aug 20 – 27

R2,932 ZAR per night
Guest favorite

Farm stay in Hampshire

4.9 out of 5 average rating, 141 reviews

Room with a view

Mar 3 – 10

R1,503 ZAR per night
Guest favorite

Apartment in Compton

4.98 out of 5 average rating, 224 reviews

The Annexe at Longacre, near Winchester

Dec 22 – 29

R2,507 ZAR per night
Guest favorite

Cottage in Privett

4.97 out of 5 average rating, 405 reviews

The Barn @ North Lodge -Soho Farmhouse-esque Cabin

Feb 1 – 8

R2,494 ZAR per night
Guest favorite

Townhouse in Hampshire

4.99 out of 5 average rating, 160 reviews

Entire House Central Winchester 2bed private patio

Jan 15 – 22

R4,092 ZAR per night
Guest favorite

Guest suite in Micheldever Station

4.98 out of 5 average rating, 109 reviews

The Tower House Studio

Oct 20 – 27

R1,818 ZAR per night
Guest favorite

Guest suite in Hampshire

4.95 out of 5 average rating, 124 reviews

Pretty self contained annexe

Sep 10 – 17

R1,371 ZAR per night

Other great vacation rentals in Winchester

Guest favorite

Home in Winchester

4.94 out of 5 average rating, 296 reviews

Oak Framed Barn with Tennis Court

Nov 11 – 18

R4,316 ZAR per night
Superhost

Apartment in Kings Worthy

4.79 out of 5 average rating, 160 reviews

Cosy and peaceful studio annex with ample parking.

Apr 19 – 26

R1,166 ZAR per night
Guest favorite

Cottage in Upham

4.95 out of 5 average rating, 199 reviews

The Stables, luxury country cottage nr Winchester

Sep 23 – 30

R3,274 ZAR per night
Guest favorite

Hut in Winchester

5.0 out of 5 average rating, 153 reviews

Nature’s Nook Cosy Couples Woodland Cabin Hursley

Jul 8 – 15

R3,913 ZAR per night
Guest favorite

Apartment in Alresford

4.93 out of 5 average rating, 106 reviews

Stunning apartment in the heart of New Alresford

Sep 25 – Oct 2

R2,283 ZAR per night
Guest favorite

Guesthouse in Hampshire

4.92 out of 5 average rating, 171 reviews

Beautiful Self Contained Annex in South Downs NP

May 21 – 28

R1,790 ZAR per night
Guest favorite

Home in Crawley

4.96 out of 5 average rating, 265 reviews

Secluded and peaceful home in beautiful village

Jul 21 – 28

R2,347 ZAR per night
Guest favorite

Tiny home in Saint Mary Bourne

4.97 out of 5 average rating, 100 reviews

Quaint Newly Converted Home

Oct 14 – 21

R2,634 ZAR per night
Guest favorite

Condo in Hampshire

4.93 out of 5 average rating, 90 reviews

Bright Bijou Studio in Central Winchester

Apr 18 – 25

R1,841 ZAR per night
Guest favorite

Apartment in Hampshire

4.83 out of 5 average rating, 24 reviews

Flat in central Winchester

Oct 28 – Nov 4

R2,379 ZAR per night
Guest favorite

Condo in Hampshire

5.0 out of 5 average rating, 27 reviews

Spacious Central Winchester 1 Bedroom Flat

Jun 18 – 25

R2,234 ZAR per night
Guest favorite

Condo in Winchester

4.92 out of 5 average rating, 73 reviews

Lovely 1 bedroom flat in Winchester with parking

Dec 6 – 13

R2,117 ZAR per night

Quick stats about vacation rentals in Winchester

Total rentals

310 properties

Wifi availability

300 properties include access to wifi

Rentals with dedicated workspaces

120 properties have a dedicated workspace

Pet-friendly rentals

80 properties allow pets

Family-friendly rentals

150 properties are a good fit for families

Total number of reviews

16K reviews

Frequently Asked Questions

  • What are some of the best things to do in Winchester?

    Take a walk through the vibrant Winchester Farmers Market, visit Winchester Science Centre for interactive exhibits, or explore Winchester College, one of the oldest schools in the country. For a touch of culture, visit the Theatre Royal Winchester for a performance.

  • What is the best time of year to visit Winchester?

    Many visitors explore Winchester from June to August when there's plenty of sunshine and the Winchester Hat Fair, a free outdoor arts festival, enlivens the city. Another popular time is during the Winchester Christmas Market in late November to December.

  • What are the best places to stay in Winchester?

    The city centre, with its proximity to historical sites and vibrant eateries, is a favourite amongst visitors. St. Cross, known for its peaceful ambiance, and Hyde, within walking distance of the city centre, are also popular. For a rural retreat, consider the surrounding Hampshire countryside.

  • What are the best places to visit in Winchester?

    Winchester Cathedral, one of the largest cathedrals in Europe, is often recommended. Other frequently suggested places include Winchester City Mill, a working watermill, and the Great Hall, home to King Arthur's Round Table. For history lovers, the Winchester City Museum is a must.

  • What are some hiking trails in Winchester?

    Explore the South Downs Way, a long-distance footpath spanning 100 miles (160 km), or the shorter but equally enjoyable St. Catherine's Hill, offering spectacular views of the city. Alternatively, immerse yourself in the natural beauty of the Itchen Navigation Heritage Trail, a serene walk along the Itchen River.

  • What are some family activities to do in Winchester?

    Families can enjoy a fun-filled day at Marwell Zoo, home to hundreds of exotic and endangered animals, or learn about the natural world at Winchester Science Centre. The interactive Winchester City Museum and the Military Museums are also popular with families.

  • What are some of the best day trip ideas in Winchester?

    Consider a day trip to the ancient Stonehenge, located about 40 miles (64 km) from Winchester. Another frequently suggested trip is to the beautiful New Forest National Park, just 23 miles (37 km) away. The historic city of Bath, known for its Roman-built baths, is also within reach at 54 miles (87 km).

  • Are there vacation rentals with a dedicated workspace in Winchester?

    Yes! Work meets play with ease at over 120 vacation rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winchester?

    Four-legged friends are welcome in Winchester. Choose from more than 80 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in townhouse rentals in Winchester?

    Experience the best of Winchester with our townhouse rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore

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  4. Hampshire
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