
Holiday rentals in Winchester
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Top-rated holiday rentals in Winchester
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Spacious central 2 bedroom apartment+ free parking
A spacious family-friendly 2 double/twin bedroom first floor flat located in the lovely Hyde area of central Winchester. Provides easy access to the city centre with all that the city offers. Only 5 minutes stroll to the train station. This apartment is close to all the historical sites and wide variety of restaurants and cafes which you'll enjoy as well as the cathedral and its impressive grounds. Winchester Christmas market and the city's magical atmosphere should be on everybody's calendar.

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.

St Michael's Hall, City Centre
St Michael's Hall is a unique, newly renovated church hall in the heart of the historic city centre. A stone's throw from the Cathedral, College, buzzy high street and water meadows, it's the perfect base to explore everything Winchester and the surrounding area has to offer. Each bedroom has its own bathroom, meaning it's as suitable for two couples as it is for a romantic city break or four friends. One on-street parking permit is available, while the train station is a short walk away.

The Pigsty
The Pigsty is Winchester's first luxury woodland hideaway, with beautiful views of Vale Farm. Less than 2.5 miles from the historic centre of Winchester, this peaceful retreat is perfect for those looking to visit the city, or escape for some peace. The Pigsty’s domed design with wooden interior has a roll top bath, cosy open plan living space and decking area to enjoy dinner with sunset views. Just a few minutes walk from the famous Clarendon Way, and a 30 minute walk to the city centre.

Studio in Abbots Worthy
Beautiful self-contained studio with its own front door, step free access and parking for one car in the charming hamlet of Abbots Worthy. Situated in the Itchen Valley, between the Cathedral City of Winchester (8 min drive) and Georgian Market Town of Alresford (10 min drive). Super-king bed (can also be made into two single beds) with luxury bedding and towels. Ensuite shower room. Wifi, Sky TV, coffee machine, fridge, microwave, hob, toaster, kettle, iron, hairdryer, wardrobe & hangers

The Hangar - countryside views, seclusion & peace.
The Farley Hangar is a peaceful space with far reaching views of Hampshire's woodlands and the Isle of Wight. Located on our family farm and private airstrip in the Test Valley. Winchester, Romsey and Stockbridge are just 20 mins away. On the doorstep of numerous cycle routes and footpaths including the Claredon Way (Sals-Win). King size bed & full-size bath with rain shower. From your private deck with log burner you will see various wildlife species and watch the stars at night.

Nature’s Nook Cosy Couples Woodland Cabin Hursley
Nature's Nook offers guests the perfect rural escape. You will be treated to spectacular views across the Winchester countryside and wildlife right outside your doorstep. Nature's Nook is perfectly located, nestled on the edge of a bluebell woodland with country walks just minutes away and the historical city of Winchester a short drive away. Curl up on the sofa with a book, sit outside by the fire pit, whilst enjoying a drink, or just relax and admire the stunning scenery!

Stable Cottage Beauworth Southdowns Hampshire
Welcome to Stable Cottage, your idyllic getaway. Our newly built cottage is designed to the highest standard for your comfort and enjoyment. The cozy atmosphere is enhanced by super-insulated walls and a log-burning stove that keep you warm during colder months. In summer, the sliding patio doors let in sunshine and stunning views of the Hampshire countryside. Stay connected with super-fast fibre broadband and a Smart TV. Your stay at Stable Cottage will be unforgettable.

Room with a view
You’ll love sharing photos of this unique place with your friends. Room with a View is a cosy and bright studio room located in the outskirts of the rural village of Owslebury. Just a 5-mile drive from the medieval city of Winchester, Room with a View is situated in a prime location, perfect for a serene getaway or business stay. Secluded from the busy bustle of the city, yet a swift 10-minute drive, Room with a View is surrounded by acres of fields and beautiful views.

The Glade at Ladyhill Vineyard near Winchester
Nestled on the edge of an ancient wood in South Downs National Park and with fantastic views over Ladyhill Vineyard and the Hampshire countryside The Glade has a cosy A-Frame to grab a good night sleep, a separate shower room with flushable loo to keep you fresh and a kitchen equip-for-easy glamping. Relax and admire the views, BBQ on the fire pit, spot deer and hare or stroll down the river Itchen to The Bush gastro pub. You’ll return home totally refreshed!

Beautiful guest suite in Hampshire
Set in the grounds of a Grade II listed thatched cottage on the edge of Kings Worthy village, our annex is beautifully decorated and comfortable. With its own entrance and small private outdoor area, this property combines rural charm and handy local amenities (bus stop just outside to central Winchester and fantastic local pub just a two minute walk away). Tea and coffee are provided as well as breakfast cereals, bread/butter and fruit jams.

Stylish Apartment • Central Winchester
Situated in the heart of Winchester, this newly refurbished two-bedroom apartment with its own private entrance offers a stylish and comfortable stay for couples, friends and families. Modern décor and thoughtful design create a cosy space to relax after exploring the city’s historic streets, shops and cathedral. You’re just steps from the popular St James Tavern, a welcoming traditional pub serving excellent locally sourced food.
Popular amenities for Winchester holiday rentals
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Summer Riverside Escape Near Winchester

Martyr Worthy Home with a View
Frequently Asked Questions
What are the best places to stay in City of Winchester?
Explore accommodations near the historic centre, around the Cathedral Quarter, or in leafy neighborhoods near the river. The city has both characterful homes and family-friendly vacation rentals in quiet residential areas.
What are the best things to do in City of Winchester with kids?
Families often enjoy exploring Winchester Cathedral, interactive exhibits at Winchester City Museum, and walkable green spaces like Abbey Gardens. Seasonal events and local parks are frequently suggested for younger visitors.
What are some of the best things to do in City of Winchester?
Explore the historic Winchester Cathedral, wander the Great Hall, and stroll through guided walks along the River Itchen. Locally rooted shops, museums, and green spaces are often recommended.
How is the weather in City of Winchester?
Winchester has cool, wetter winters averaging 35–47°F (2–8°C), with milder, comfortably warm summers near 54–72°F (12–22°C). Rainfall is spread through the year, so packing layers and a waterproof jacket is useful.
When is the best time to visit City of Winchester?
Late spring through early fall is often recommended for milder temperatures, blooming gardens, and outdoor events. Winter brings festive decorations, while autumn features colorful foliage along city walks.
What are the best places to visit in City of Winchester?
The city has historic attractions such as Winchester Cathedral and the Great Hall, plus tranquil spaces like Abbey Gardens. The City Museum and riverside walks are frequently suggested by visitors.
What are some hiking trails in City of Winchester?
Winchester has scenic paths along the River Itchen and through St. Catherine's Hill, often recommended for gentle hikes or panoramic views. The city is also a starting point for longer routes like the South Downs Way.
What are some family activities we can do in City of Winchester?
Families can explore hands-on exhibits at Winchester City Museum, picnic in Abbey Gardens, or follow historic-themed treasure trails around the city centre. Parks and seasonal events make the city welcoming for all ages.
What are some of the best day trip ideas from City of Winchester?
Popular day trips include historic sites in Salisbury, nature reserves in the South Downs, and local villages known for their markets. The surrounding Hampshire countryside has gardens and walking trails frequently suggested by locals.
Are there any pet friendly accommodations available in City of Winchester?
Winchester has pet-friendly vacation rentals, with many hosts welcoming pets in residential neighborhoods near parks and green spaces. The city’s walking paths and gardens appeal to those traveling with animals.
What are some local tips for visiting City of Winchester?
Arrive early for quieter walks at the Cathedral or city markets, and explore side streets for independent shops and cafes. Check seasonal events before you go, and wear comfortable shoes for cobblestone paths.
What is City of Winchester known for?
Winchester is known for its medieval history, including Winchester Cathedral and the Great Hall with King Arthur’s legendary Round Table. The city has a tradition of locally rooted markets and cultural heritage.
What are the best hidden gems to explore in City of Winchester?
Consider exploring St. Catherine’s Hill for panoramic views, tucked-away water meadows along the River Itchen, or art at local galleries. Independent bookshops and historic pubs add character around quieter lanes.
What are the best foods to try in City of Winchester?
Winchester has traditional English pies, locally sourced cheeses, and seasonal produce often found at city markets. Artisan bakeries and cafes serve specialties like Hampshire watercress soup and homemade cakes.
What should I bring for a trip to City of Winchester?
Pack weather-appropriate layers, comfortable walking shoes, and a waterproof jacket since conditions can be changeable. An umbrella, reusable water bottle, and camera are useful for exploring city sites and parks.
What is the nightlife in City of Winchester like?
Nightlife in Winchester has cosy pubs, wine bars, and occasional live music venues around the city centre. Some historic pubs host quiz nights or storytelling events, with a relaxed, welcoming atmosphere.
What are the most popular events or festivals in City of Winchester?
Winchester is known for its festive Christmas market, seasonal food festivals, and annual literary events often held around the Cathedral and city centre. Cultural celebrations mark spring and summer weekends.
Are there family friendly vacation rentals in City of Winchester?
Winchester has family-friendly vacation rentals in neighborhoods near parks, schools, and city attractions. Many hosts provide amenities for children, with easy access to local green spaces and playgrounds.
Quick stats about holiday rentals in Winchester

Total holiday rentals
Explore 2,660 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 117,650 verified reviews to help you choose

Family-friendly holiday rentals
1,160 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 650 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
1,320 properties have a dedicated workspace

Wifi availability
2,560 of Winchester holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winchester rentals

4.7 Average rating
Winchester stays receive an average rating of 4.7 out of 5 from guests
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- New Forest National Park
- Bournemouth Beach
- West Wittering Beach
- Paultons Park Home of Peppa Pig World
- University of Oxford
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- Stonehenge
- Thorpe Park Resort
- Longleat Safari Park
- Chessington World of Adventures Resort
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- Bracklesham Bay
- Hampton Court Palace
- Highclere Castle
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- Mudeford Quay
- Goodwood Racecourse
- Winchester Cathedral
- The Tank Museum
- Ascot Racecourse
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