
Vacation rentals in Winchester
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Winchester
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester vacation rentals
House rentals in Winchester

Mainsail

One bedroom house in Waterlooville. An ideal base.

Charming Modern Victorian 2 bed with FREE parking

4 bedroom house in seaside town

Contractors/4bed house w/parking/Discount!

Whole seaside apt, stones throw to the new forest.

Modern 2 bedroom house 5 minutes from the beach

Delightful Sunny House Close to the Village Square
Apartment rentals in Winchester

One bedroom flat in Marlow

Beach front apartment

Smart West Reading apartment: car only parking bay

Beautiful 2-bed 2-bath, Walk 2 Beach, Free Parking

Centrally located apartment- FREE off road parking

3Bed Garden Apt. Clifftop, sleeps 8 with Hot Tub

Modern apartment with stunning sea views,

Malthouse Court - Premium 1-Bed 2-Bath w/ Balcony
Pet-friendly vacation rentals in Winchester

Pet friendly annexe **ALBEIT TIME** (not no.1)

Sea Kisses - A Mudeford gem located close to beach

Little Cowdray Glamping - The Log Cabin

Seaview dog friendly ground floor flat sleeps 4

Gardeners cottage-pet friendly,New forest bolthole

No3. Yarmouth Country Cottages

Cosy retreat with woodfired bathtub

Waterfront, character cottage
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).
Do house rentals in Winchester have self check-in?
Absolutely! We offer over 30 house rentals with self check-in in Winchester. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in cottage rentals in Winchester?
Experience the best of Winchester with our cottage rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Destinations to explore
- River Thames Vacation rentals
- Oxford Vacation rentals
- South London Vacation rentals
- Cotswolds Vacation rentals
- Cotswold District Vacation rentals
- Royal Borough of Kensington and Chelsea Vacation rentals
- City of Westminster Vacation rentals
- London Vacation rentals
- Central London Vacation rentals
- London Borough of Camden Vacation rentals
- Inner London Vacation rentals
- City of London Vacation rentals
- Rentals with a patio Winchester
- Apartment rentals Winchester
- Rentals with breakfast Winchester
- Pet-friendly rentals Winchester
- Cottage rentals Winchester
- Family-friendly rentals Winchester
- Cabin rentals Winchester
- Rentals with outdoor seating Winchester
- Condo rentals Winchester
- Kid-friendly rentals Winchester
- Rentals with a washer and dryer Winchester
- Rentals with a fireplace Winchester
- House rentals Winchester
- Townhouse rentals Winchester
- Villa rentals Winchester
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- New Forest national park
- Bournemouth Beach
- Boscombe Beach
- Oxford University
- Southbourne Beach
- Winchester Cathedral
- Paultons Park Home of Peppa Pig World
- Goodwood Motor Circuit
- Hampton Court Palace
- Stonehenge
- Port Meadow
- West Wittering Beach
- Arundel Castle
- Chessington World of Adventures Resort
- Tapnell Farm Park
- Highclere Castle
- RHS Garden Wisley
- Goodwood Racecourse
- The Tank Museum
- Marwell Zoo
- Thorpe Park Resort
- Sunningdale Golf Club,
- Bushy Park
- Poole Quay
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes