Winchester vacation rentals

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Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

The Great Hall55 locals recommend
Winchester Christmas Market11 locals recommend
Theatre Royal Winchester41 locals recommend
Sainsbury's7 locals recommend
St Catherine's Hill55 locals recommend
Tesco Extra27 locals recommend

Other great vacation rentals in Winchester

Guest favorite

Shepherd’s hut in Winchester

4.96 out of 5 average rating, 331 reviews

Shepherd's Hut with Hot Tub near Winchester

Sep 18 – 25

G$30,116 GYD per night
Guest favorite

Guest suite in Hampshire

4.87 out of 5 average rating, 209 reviews

The Annexe-central Winchester

Aug 18 – 25

G$19,215 GYD per night
Guest favorite

Guesthouse in Hampshire

4.97 out of 5 average rating, 145 reviews

The Lodge Winchester

Oct 6 – 13

G$35,170 GYD per night
Guest favorite

Guest suite in Winchester

4.89 out of 5 average rating, 140 reviews

Beautiful guest suite in rural Hampshire

Jan 2 – 9

G$23,109 GYD per night
Guest favorite

Cottage in Hampshire

5.0 out of 5 average rating, 171 reviews

Cosy country cottage with chalk stream charm

Oct 1 – 8

G$38,248 GYD per night
Guest favorite

Hut in Winchester

4.97 out of 5 average rating, 462 reviews

The Pigsty

Sep 30 – Oct 7

G$49,068 GYD per night
Guest favorite

Guest suite in Hampshire

4.95 out of 5 average rating, 129 reviews

Pretty self contained annexe

Sep 23 – 30

G$14,324 GYD per night
Guest favorite

Guesthouse in Hampshire

4.9 out of 5 average rating, 306 reviews

Cosy Annexe in a beautiful part of Winchester

Jul 27 – Aug 3

G$19,768 GYD per night

Other great vacation rentals in Winchester

Guest favorite

Cottage in Privett

4.97 out of 5 average rating, 413 reviews

The Barn @ North Lodge -Soho Farmhouse-esque Cabin

Oct 9 – 16

G$27,761 GYD per night
Guest favorite

Condo in Hampshire

4.94 out of 5 average rating, 196 reviews

Lovely 2 Bedroom Flat

Jul 24 – 31

G$26,468 GYD per night
Guest favorite

Farm stay in Hampshire

4.9 out of 5 average rating, 146 reviews

Room with a view

Mar 11 – 18

G$16,323 GYD per night
Guest favorite

Home in Meonstoke

5.0 out of 5 average rating, 114 reviews

The Piggery: with tennis court and games barn

May 24 – 31

G$36,911 GYD per night
Guest favorite

Cottage in Winchester

4.82 out of 5 average rating, 246 reviews

Beggar's Lane Cottage-3 beds in Central Winchester

Feb 6 – 13

G$41,591 GYD per night
Guest favorite

Guest suite in Hampshire

4.96 out of 5 average rating, 243 reviews

The Oaks, Twyford Moors, South Downs National Park

Oct 4 – 11

G$24,420 GYD per night
Guest favorite

Home in Crawley

4.96 out of 5 average rating, 266 reviews

Secluded and peaceful home in beautiful village

Nov 6 – 13

G$26,017 GYD per night
Guest favorite

Apartment in Hampshire

4.84 out of 5 average rating, 32 reviews

Flat in central Winchester

Feb 23 – Mar 2

G$26,533 GYD 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

    130 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

  • How is the weather in Winchester?

    Winchester experiences a temperate maritime climate with mild winters and warm summers. Average highs in summer are around 70°F (21°C), while in winter, temperatures hover around 45°F (7°C). Rainfall is distributed fairly evenly throughout the year.

  • 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 130 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.

Destinations to explore

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