
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.

Central, Quiet & Self-Contained
Incredibly central location. Only 150m from Cathedral & 200m to High St. Quiet: Set back from the street, double glazing, detached building. King size bed with luxury mattress & topper, hypoallergenic duvet & pillows, Egyptian cotton bedlinen and fluffy towels. Work space. Reading & soft lighting. Well Equipped: Tea & Coffee Facilities, Mini Fridge, TV (Netflix only) Iron+Board, Hairdryer, Toiletries & Fan. Secure parking subject to availability £20per night. NB. Access via external staircase.

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.

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.

The Piggery: with tennis court and games barn
The Piggery is a secluded flint built hideaway, with lots of period charm, set in the grounds of a manor house. Converted to a high standard it has it’s own private garden, access to the owners tennis court & a large barn with table tennis, table football & pool, wider house grounds including an island, surrounded by the river Meon. Numerous walks direct from The Piggery and a number of local vineyards are nearby. 5/10mins walk away are two super pubs and the very well stocked village shop.

Oak Framed Barn with Tennis Court
A stylish secluded, two storey, oak framed barn with tennis court, 4 miles from Winchester. Homely space with two bedrooms plus a sofa bed (upon request) and ground floor open plan living area. Super fast WiFi. The Barn adjoins the Watercress Way and stands separately in the grounds with views over open Hampshire fields. Nearest neighbour c.1 mile away but there is loads to do in the area with an abundance of country pubs, one or two within walking distance and beaches within 50 minutes

Beautiful stylish Garden flat 8 mins to Winchester
Unique and stylish, this very comfortable and relaxing space offers the peacefulness of countryside whilst being a stones throw from the beautiful city of Winchester - a very short drive or a beautiful walk away. You get the best of both worlds with the city's pubs, restaurants, cafes and historic sights close at hand as well as river walks by the Itchen & beautiful countryside straight from your door. Excellent transport links to London, M3, Southampton Airport and the New Forest.

Central Winchester 1 Bedroom Home with own parking
Welcome to your lovely detached one bedroom home in a quiet leafy private road on the edge of St Giles Hill - just above medieval Winchester and on the edge of beautiful the South Downs Way. Your self-contained home includes parking on the drive, a stylish double bedroom, shower room, living area (with full double-width sofa bed) incorpoating a full kitchen/washing machine. Its an easy 10 minute downhill stroll across the park (lovely for a sunset picnic) to historic Winchester.

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.

Bright Bijou Studio in Central Winchester
A beautiful bright cosy studio apartment on one of the quietest streets in the centre of historic Winchester❤️. The breathtaking cathedral and other must-see sights are all within a flat 10 minute walk. Ideal for short stays or a weekend get-away. Just five minutes walk from train station/city centre, and 10 mins walk from the bus station. * Super-comfy double bed ✅ * Fast WiFi ✅ * Comfortable big chair and table for laptop working ✅ * Wide range of caf/decaf teas and coffees ✅

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!
Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester

Annex@Capers End

Luxury Cabin with Outdoor Bath, Sauna & Fireplace

Private cosy room · No kitchen · Free parking

A new detached Studio Annexe

Cosy Shepherd's hut - Hensting Valley Park

Studio Flat 3rd Floor

Boutique Flat | 1-min Station | Pub | River Walks

Summer Riverside Escape Near Winchester
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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