Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Winchester

  • Total vacation rentals

    Explore 310 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at G$4,184 GYD per night before taxes and fees

  • Verified guest reviews

    Over 19,850 verified reviews to help you choose

  • Family-friendly vacation rentals

    160 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    300 of Winchester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Winchester rentals

  • 4.8 Average rating

    Winchester stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1
Top guest favorite
A light-filled living area features a comfortable gray sofa adorned with patterned cushions. A small, cozy armchair sits nearby, and a wooden coffee table is positioned in front. Natural light streams through the window, highlighting a light blue wall and decorative shelf.
Condo in Winchester
4.96 out of 5 average rating, 177 reviews

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.

Top guest favorite
A well-appointed room features a spacious bed with plush bedding. Light wood flooring complements the seating area with a circular table and two upholstered chairs. Skylights and decorative lamps provide soft lighting. A mirror adds depth, and a hairdryer is available on the wall.
Guesthouse in Winchester
4.91 out of 5 average rating, 150 reviews

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.

Top guest favorite
The exterior of a charming two-story annexe is displayed, featuring a sloped roof and large windows. The entrance is framed by two potted plants, with a gravel pathway leading to a spacious area of green lawn and hedges surrounding the property.
Place to stay in Compton
5 out of 5 average rating, 128 reviews

Understated luxury at The Annexe

The Annexe is a unique and stylish self-contained unit over two floors. High spec accommodation including a kitchen-diner-lounge, TV & wet room on the ground floor & king size bed, desk, TV and spin bike located upstairs. Well appointed on a private leafy lane 3 miles from Winchester. Picturesque walks are right on the doorstep and it is an ideal ‘escape’ to explore historic Winchester and enjoy the lovely Hampshire countryside on the edge of the South Downs and River Itchen. Understated luxury!

Top guest favorite
A quiet street is lined with period houses, showcasing a mix of red brick and white facades. The cobblestone pavement leads past quaint buildings, with clear blue skies overhead. Architectural details include shuttered windows and gabled roofs, creating a charming urban atmosphere.
Townhouse in Winchester
4.99 out of 5 average rating, 172 reviews

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.

Top guest favorite
The Pigsty features a unique domed structure with a blend of dark and natural wood accents. A small outdoor seating area with a round table and two chairs is positioned at the entrance, surrounded by lush greenery and potted plants.
Hut in Winchester
4.98 out of 5 average rating, 642 reviews

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.

Top guest favorite
A polished silver bowl filled with ice displays several bottles of champagne. Fresh lilies and elegant candelabras are positioned nearby, adding a touch of sophistication to the setting. The arrangement creates a celebratory atmosphere.
Apartment in Winchester
5 out of 5 average rating, 106 reviews

The Sky Penthouse, City Centre Luxury

Positioned right in the heart of charming historic Winchester The Sky Penthouse offers luxury modern comfortable 5 star accommodation . Private parking for one car . Positioned an easy level 300 meter walk from the main High Street within the City Centre , 400 meters from Winchester Cathedral and 500 meters from Winchester train station. Great location with a garden. Guests can choose the bed configuration of both the double bedrooms, either 6ft wide super king luxury beds or single beds.

Top guest favorite
The exterior of the garden flat is showcased, featuring a sloped roof and large glass doors that open to a spacious terrace. A well-manicured lawn surrounds the building, and a dog relaxes peacefully in the grass. Lush greenery and garden beds enhance the inviting outdoor space.
Condo in Compton
5 out of 5 average rating, 133 reviews

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.

Top guest favorite
A charming brick and flint building is surrounded by neatly trimmed bushes and a well-maintained garden. Two wooden chairs and a small table are set outside, inviting guests to enjoy the tranquil rural setting under clear skies.
Guesthouse in Winchester
4.97 out of 5 average rating, 584 reviews

Idyllic Hideaway Ham Green Cottage near Winchester

The Orchard Studio at Ham Green Cottage is a pretty brick and flint building tucked away in a corner of our truly English country garden. You are completely private. We are family-friendly and you can expect a comfortable stay and warm welcome. We are in a village close to the historic city of Winchester, however our setting is completely rural and quiet. We have a fantastic village pub or there are lots of places to chose from in Winchester itself - the best of both worlds!

Top guest favorite
The lounge area features a comfortable sofa adorned with colorful cushions and a light rug underfoot. A small armchair adds seating options, while natural light filters through the large windows, illuminating the room. A round coffee table rests in the center, enhancing the cozy atmosphere.
Apartment in Winchester
4.95 out of 5 average rating, 410 reviews

Central Winchester garden flat, permit parking

Winchester City Centre- Bijou, charming, characterful, homely, warm and cosy self contained one bedroom flat with free permit parking and luxuriously large bath tub with shower, private garden with patio for alfresco dining. Fully equipped galley kitchen for self - catering. Only a five minute level walk to the central High Street and Cathedral, with the world famous Christmas Market through November and December. Less than ten minutes walk from the Railway Station.

Guest favorite
An A-frame structure is framed by trees and surrounded by blooming bluebells. Light filters through the open front, illuminating the interior where a seating area is presented. The natural setting offers a serene escape, with vibrant flowers in the foreground enhancing the tranquil scene.
Hut in Ovington
4.97 out of 5 average rating, 172 reviews

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!

Top guest favorite
The living room features a light and airy design, showcasing a two-seater sofa and a separate sofa bed. A dining table for four is centered in the space, complemented by a fireplace and a wall-mounted TV. Decorative plants enhance the welcoming atmosphere.
Apartment in Winchester
4.93 out of 5 average rating, 238 reviews

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.

Guest favorite
A modern living space is visible through open bi-fold doors, blending indoor and outdoor areas. A sleek seating arrangement is placed outside on a patio, complemented by soft lighting. Inside, a light-filled room showcases a comfortable sofa and dining area, enhancing the welcoming atmosphere.
Tiny home in Winchester
4.95 out of 5 average rating, 285 reviews

The Hidden house in Winchester

The Hidden House is a slice of modern luxury tucked away in the heart of Winchester. Detached and private, this space is perfectly placed for exploring Winchester and all it has to offer. Our guests also love hiding away and making use of the big TV setup and Hotel Chocolat Velvetiser! Don't take our word for it - check out our reviews. Winchester High Street/The Cathedral - 10 min walk Winchester Train Station - 5 min walk

Popular amenities for Winchester vacation rentals

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$32,635 GYDG$32,844 GYDG$32,216 GYDG$33,262 GYDG$33,680 GYDG$33,890 GYDG$35,145 GYDG$36,609 GYDG$37,446 GYDG$36,191 GYDG$34,517 GYDG$37,237 GYD
Avg. temp5°C5°C7°C9°C12°C15°C17°C17°C15°C11°C8°C5°C

Frequently Asked Questions

  • What are the best places to stay in Winchester?

    Winchester has a mix of accommodation options around the historic city centre, near the railway station, and just outside in residential neighborhoods. Many visitors choose areas that provide easy access to the Cathedral, local restaurants, museums, and small shops.

  • What are the best things to do in Winchester with kids?

    Families can explore Winchester Science Centre, wander the historic streets, or visit riverside parks for outdoor play. The Great Hall, home to the legendary Round Table, is also frequently suggested for curious young visitors.

  • What are some of the best things to do in Winchester?

    Explore Winchester Cathedral, stroll along the River Itchen, and visit the Great Hall to learn about local legends. Markets, galleries, and walking trails give a taste of the city's vibrant community.

  • How is the weather in Winchester?

    Winchester experiences cool, damp winters averaging 35–47°F (2–8°C), and mild summers near 54–72°F (12–22°C). It is a good idea to pack layers and a light waterproof jacket throughout the year.

  • When is the best time to visit Winchester?

    Late spring through early autumn is often recommended for milder temperatures and outdoor activities. Seasonal festivals and historic sites draw visitors year-round, but gardens and walking routes are especially lively in warmer months.

  • What are the best places to visit in Winchester?

    Winchester has the acclaimed Winchester Cathedral, the Great Hall with its medieval history, and riverside walks along the Itchen. City museums and markets around the centre are frequently suggested for visitors.

  • What are some hiking trails in Winchester?

    The South Downs Way passes near Winchester and has scenic countryside paths suitable for walking. Riverside trails along the Itchen and routes through nearby nature reserves also attract hikers and families.

  • What are some family activities we can do in Winchester?

    Families enjoy interactive exhibits at Winchester Science Centre, picnics in Abbey Gardens, and the city's historic walking tours. The Great Hall and parks around the centre are local favourites for a relaxed outing.

  • What are some of the best day trip ideas from Winchester?

    Travellers often take day trips to the New Forest for woodland walks, Salisbury and its cathedral, or tour nearby villages known for local produce and markets. Coastal spots around Hampshire also appeal to visitors.

  • Are there any pet friendly accommodations available in Winchester?

    Winchester has pet-friendly stays, especially in neighbourhoods near parks and walking trails. Many hosts welcome dogs, making it easy to enjoy outdoor spaces together.

  • What are some local tips for visiting Winchester?

    Try exploring early in the day for fewer crowds at popular sites like Winchester Cathedral. Local markets and independent cafes are scattered throughout the centre, and walking shoes help on cobbled and uneven streets.

  • What is Winchester known for?

    Winchester is known for its rich medieval history, impressive Cathedral, and connections to legends such as King Arthur’s Round Table. The city also has a reputation for vibrant markets and lively community events.

  • What are the best hidden gems to explore in Winchester?

    Seek out Wolvesey Castle, the quiet grounds of St. John’s Almshouses, and the water meadows just beyond the city centre for peaceful walks. Independent bookshops and small art galleries are also worth exploring.

  • What are the best foods to try in Winchester?

    Local menus frequently suggest Hampshire watercress, artisan cheeses, and seasonal game dishes. Independent bakeries feature British pastries, and area pubs often serve classics like fish and chips.

  • What should I bring for a trip to Winchester?

    Bring comfortable walking shoes for cobbled streets and local trails, a waterproof jacket for changeable weather, and layers to accommodate cool mornings and warmer afternoons. A camera is handy for historic architecture and scenic views.

  • What is the nightlife in Winchester like?

    Winchester’s nightlife features relaxed pubs, live music venues, and wine bars around the centre. Many spots celebrate local brews and host evening events in historic settings.

  • What are the most popular events or festivals in Winchester?

    Winchester has recurring events such as the Winchester Christmas Market, a well-attended food festival in summer, and seasonal literary celebrations. The city’s calendar often features music, arts, and outdoor gatherings.

  • Are there family friendly vacation rentals in Winchester?

    Family-friendly rentals are found across Winchester, particularly near the city centre and parks. Many hosts provide amenities for young guests, making it easy to relax after days spent exploring historic and outdoor attractions.

  1. Airbnb
  2. United Kingdom
  3. England
  4. Hampshire
  5. Winchester