
Vacation rentals in Winchester
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Top-rated vacation rentals in Winchester
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Vacation rentals for every style
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Popular amenities for Winchester vacation rentals
Pet-friendly vacation rentals in Winchester

Peaceful barn conversion in rural location.

Adventure Prospect - Historic Waterfront Cottage

The Barn @ North Lodge -Soho Farmhouse-esque Cabin

Nettlebed Farm Holiday Lets, Barn1 of 3

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath

Stunning apartment in the heart of New Alresford

Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB

The Granary, self-contained B&B near Petersfield
Other great vacation rentals in Winchester

The Stables, luxury country cottage nr Winchester

Spacious central 2 bedroom apartment+ free parking

The Treehouse at Barrow Hill Barns

Room with a view

Self Contained Studio in Winchester

Martyr Worthy Home with a View

Secluded and peaceful home in beautiful village

Entire House Central Winchester 2bed private patio
Quick stats about vacation rentals in Winchester
Total rentals
300 properties
Total number of reviews
17K reviews
Family-friendly rentals
140 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Wifi availability
300 properties include access to wifi
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).
How much does it cost to stay in condo rentals in Winchester?
Experience the best of Winchester with our condo rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there house rentals with a dedicated workspace in Winchester?
Yes! Work meets play with ease at over 50 house rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.
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- New Forest national park
- Bournemouth Beach
- Paultons Park Home of Peppa Pig World
- Kimmeridge Bay
- Oxford University
- Boscombe Beach
- Stonehenge
- Goodwood Motor Circuit
- Windsor Castle
- Hampton Court Palace
- Southbourne Beach
- Lower Mill Estate
- Chessington World of Adventures Resort
- West Wittering Beach
- Thorpe Park Resort
- Arundel Castle
- Highclere Castle
- Goodwood Racecourse
- RHS Garden Wisley
- Winchester Cathedral
- The Tank Museum
- Worthing Pier
- Marwell Zoo
- Highcliffe Beach