Winchester vacation rentals

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Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

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

Other great vacation rentals in Winchester

Guest favorite

Apartment in Hampshire

4.95 out of 5 average rating, 173 reviews

Romantic, artist’s flat, superb central location.

Jun 20 – 27

G$33,715 GYD per night
Guest favorite

Guest suite in Hampshire

4.95 out of 5 average rating, 127 reviews

Pretty self contained annexe

Jul 29 – Aug 5

G$14,921 GYD per night
Guest favorite

Cottage in Winchester

4.82 out of 5 average rating, 245 reviews

Beggar's Lane Cottage-3 beds in Central Winchester

May 2 – 9

G$37,464 GYD per night
Guest favorite

Home in Otterbourne

4.98 out of 5 average rating, 121 reviews

Quiet semi-detached house near Winchester

Jan 2 – 9

G$25,103 GYD per night
Guest favorite

Townhouse in Hampshire

4.99 out of 5 average rating, 163 reviews

Entire House Central Winchester 2bed private patio

Jan 11 – 18

G$44,521 GYD per night
Guest favorite

Guest suite in Winchester

4.89 out of 5 average rating, 139 reviews

Beautiful guest suite in rural Hampshire

Jul 1 – 8

G$23,217 GYD per night
Guest favorite

Condo in Hampshire

4.94 out of 5 average rating, 193 reviews

Lovely 2 Bedroom Flat

Aug 28 – Sep 4

G$27,620 GYD per night
Guest favorite

Apartment in Compton

4.98 out of 5 average rating, 226 reviews

The Annexe at Longacre, near Winchester

Dec 21 – 28

G$26,856 GYD per night

Other great vacation rentals in Winchester

Guest favorite

Hut in Winchester

4.97 out of 5 average rating, 458 reviews

The Pigsty

Mar 3 – 10

G$48,439 GYD per night
Guest favorite

Farm stay in Hampshire

4.9 out of 5 average rating, 143 reviews

Room with a view

Oct 20 – 27

G$16,351 GYD per night
Guest favorite

Cottage in Upham

4.96 out of 5 average rating, 201 reviews

The Stables, luxury country cottage nr Winchester

Jan 25 – Feb 1

G$31,165 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 26 – Dec 3

G$25,820 GYD per night
Guest favorite

Cottage in Privett

4.97 out of 5 average rating, 410 reviews

The Barn @ North Lodge -Soho Farmhouse-esque Cabin

Nov 28 – Dec 5

G$27,702 GYD per night
Guest favorite

Guesthouse in Hampshire

4.92 out of 5 average rating, 175 reviews

Beautiful Self Contained Annex in South Downs NP

Jul 1 – 8

G$19,613 GYD per night
Guest favorite

Guest suite in Hampshire

4.96 out of 5 average rating, 242 reviews

The Oaks, Twyford Moors, South Downs National Park

Aug 18 – 25

G$26,306 GYD per night
Guest favorite

Apartment in Hampshire

4.87 out of 5 average rating, 30 reviews

Flat in central Winchester

Mar 22 – 29

G$27,156 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

  • 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.

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

    Experience the best of Winchester with our townhouse rentals, starting at about $50 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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