A cathedral at night with illuminated trees and a park with benches.

City of Winchester holiday rentals

We found 1,712 holiday rentals — enter your dates for availability

Select from 53 houses, 39 apartments and other holiday rentals to find the perfect place for your stay in City of Winchester. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you need and want for your stay, which might include a hot tub and a washer and dryer. You're sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Popular City of Winchester destinations on Stayz

A sunset over a river with a bridge and buildings in the background.

Southampton

A historic building with large windows and pointed arches, surrounded by lush green trees and a grassy area with people sitting and walking.

Winchester

A military cannon, a grassy field, and a brick building with a flag.

Fareham

Waterlooville

A large neoclassical building with columns and a symmetrical facade, surrounded by a well-maintained lawn and trees.

Alresford

A beach with wooden posts in the water, a pebble beach, and a cloudy sky.

Whiteley

Holiday rentals with weekly discounts – City of Winchester

Showing deals for:20 Nov - 27 Nov

Exceptional

(7 reviews)

Luxury cottage in the stunning Hampshire countryside with garden and views.

Basingstoke

9% off

AU$2,307

for 7 nights, 1 cottage

AU$330 per night

includes taxes & fees

Exceptional

(48 reviews)

Modern House with amazing views sleeps 10

Cowes

9% off

AU$9,468

for 7 nights, 1 home

AU$1,353 per night

includes taxes & fees

Porstmouth Historic Dockyard (HMS Warrior from Spinnaker Tower)

Exceptional

(243 reviews)

'The Haven' a luxury apartment close to the Meon Shore coast.

Fareham

9% off

AU$1,257

for 7 nights, 1 apartment

AU$180 per night

includes taxes & fees

Mariners Cottage, yards from the water in Emsworth

Exceptional

(25 reviews)

Waterside Cottage In Emsworth, Hampshire

Emsworth

9% off

AU$2,160

for 7 nights, 1 home

AU$309 per night

includes taxes & fees

Exceptional

(22 reviews)

Luxurious and Cosy Holiday Lodge in the New Forest National Park

Salisbury

9% off

AU$2,104

for 7 nights, 1 room

AU$301 per night

includes taxes & fees

Exceptional

(120 reviews)

Lovely cottage & garden. 5 min drive from Paultons Park, home of Peppa Pig

Southampton

8% off

AU$2,744

for 7 nights, 1 cottage

AU$392 per night

includes taxes & fees

Exceptional

(9 reviews)

Cosy Rural Cabin With Ensuite without Pergola

Alton

18% off

AU$1,294

for 7 nights, 1 cabin

AU$185 per night

includes taxes & fees

Exceptional

(12 reviews)

Gorgeous Apartment in the heart of Winchester

Winchester

9% off

AU$3,044

for 7 nights, 1 apartment

AU$435 per night

includes taxes & fees

Exceptional

(105 reviews)

Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.

Stockbridge

9% off

AU$2,388

for 7 nights, 1 cottage

AU$341 per night

includes taxes & fees

Front terrace leading of dining/kitchen area

Your apartment at the front of the complex

Exceptional

(159 reviews)

Luxury Cowes waterfront apartment with exceptional Marina and Solent Sea Views

Cowes

8% off

AU$2,358

for 7 nights, 1 apartment

AU$337 per night

includes taxes & fees

Exceptional

(18 reviews)

Holiday Home for 5 people close to Hamble Village centre and Marinas

Southampton

9% off

AU$2,352

for 7 nights, 1 home

AU$336 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find the best place to stay - City of Winchester

Sunday Winchester Wessex Cathedral Hotel | Classic

Sleeps 2 · 1 bedroom · 1 bathroom

Curbridge Chapel a converted chapel

Sleeps 6 · 3 bedrooms · 2 bathrooms

The Down House Cottage less than 3 miles from the heart of historic Winchester.

Sleeps 2 · 1 bedroom · 1 bathroom

Contemporary Barn in Twyford just 3 miles from Winchester. Parking provided.

Sleeps 6 · 2 bedrooms · 2 bathrooms

Period Home in the Heart of Winchester

Sleeps 6 · 4 bedrooms · 2+ bathrooms

4 Bedroom Gateway: Winchester - Town Centre 4 mins.

Sleeps 10 · 4 bedrooms · 1+ bathroom

Top rated rentals - City of Winchester

Great stay

Cosy comfortable cottage within asking distance to station and town centre. Enjoyed walking to the cathedral and environs. Home away from home. After many weeks of travelling was a pleasure to do some cooking and enjoy the garden outlook. Thanks also for the Prosecco.

Kerry K.

Stayed July 2024

Image of Beautifully presented, countryside, self-contained, 1-bed apartment

Life in the country

New, clean, well equipped and comfortable. Within easy walking distance of two pubs.- (lovely meals) Not however, convenient for general shopping, or surprisingly for country walks - we tried two signposted walking tracks, both took us to houses!

Margaret K.

Stayed Apr 2024

Book a holiday rental for your City of Winchester getaway

Learn about the unique charm of City of Winchester with a stay in a holiday home rental. This city has something for everyone. Southampton Cruise Terminal and New Forest National Park are just a couple of the must-see attractions in the area. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in City of Winchester

Are you hoping to discover attractions to visit while you're in the area? Venture out of your cosy holiday rental and check out everything that makes City of Winchester a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

Marwell Zoo (4.9 mi / 7.9 km)
Broadlands Estate (9.4 mi / 15.2 km)
The Quays (11.8 mi / 19 km)
Paultons Family Theme Park - Home of Peppa Pig World (13 mi / 20.9 km)
Thruxton Kart Centre (16.2 mi / 26 km)
Basingstoke Leisure Park (16.4 mi / 26.3 km)

Exploring the natural landscape of City of Winchester

Whether you're looking for adventure or just want to appreciate the scenery, City of Winchester is a great place to spend some time outside. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

New Forest National Park (19.6 mi / 31.5 km)
Avington Park (3.3 mi / 5.4 km)
Mayflower Park (12 mi / 19.4 km)
Calshot Beach (17 mi / 27.3 km)
Exbury Gardens and Steam Railway (18.4 mi / 29.6 km)
Lepe Beach (19.2 mi / 31 km)

How to get to and around City of Winchester

If you're travelling by train, Winchester Station, Winchester Shawford Station and Winchester Micheldever Station are the main stations in the city.

Frequently asked questions

What is the best area to stay in City of Winchester when booking a holiday home?

Among the more popular areas for a City of Winchester holiday home is Twyford. When you book your stay with Stayz, you will have the entire place to yourself. So you won't have to share it with anyone except for your group.

What is the most popular type of holiday home accommodation in City of Winchester?

Based on our research, cottages are the most in-demand type of holiday property in City of Winchester. But of course, everyone's idea of an epic stay can differ. Stayz has holiday homes of all sizes, shapes and budgets, so you're sure to discover the best fit for your needs.

How much does it cost to rent a holiday home in City of Winchester?

Property type, length of stay and season are some of the conditions that can influence the price of a holiday home. Simply enter your dates of travel to find the ultimate escape. From cosy cabins to sprawling villas, all Stayz holiday homes offer unbeatable value.

How much does it cost to rent a beach house in City of Winchester?

The average price for a holiday home close to the beach in City of Winchester depends on when you're visiting the area and the size and type of property you want. You can find prices easily and quickly on Stayz by entering your destination and preferred travel dates. Then use the filters to select the number of bedrooms and amenities that you prefer, such as a pool, WiFi and air conditioning.

What are popular home amenities in City of Winchester?

Off-street parking options, a dishwasher and a washing machine are the most popular home amenities in City of Winchester. Whether you're taking to the road as a party of one, with a partner or a bunch of friends, Stayz will help you find a holiday home that suits your style with all the options you need.

Are there large group holiday homes in City of Winchester?

Take your pick of two holiday homes in City of Winchester that can sleep 10 or more guests. Whether you're planning time away with the family or an event like a party, there's plenty of room to get your group together under one roof.

What are the top attractions for families in City of Winchester?

Keeping the kids amused during your City of Winchester holiday is easy with these family-friendly attractions:

Marwell Zoo
Winchester Christmas Market
Winchester Cathedral

Can I find two-bedroom holiday homes in City of Winchester?

City of Winchester has 39 two-bedroom holiday properties to pick from. Experience a holiday home with all the privacy and comfort you need at an attractive price on Stayz.

Are there holiday homes with WiFi in City of Winchester?

You can pick from 26 holiday homes with WiFi in City of Winchester. If you want to disconnect from the world on your trip, but still need to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Stayz.

How old do you have to be to rent a holiday home in City of Winchester?

The minimum age is generally 16, 18 or 21. It can change from one property to another on Stayz, so look at the rules of your chosen City of Winchester holiday home before making a booking.

How long can I rent a holiday home in City of Winchester for?

The amount of time you can rent a City of Winchester holiday home for varies depending on the property. Just put in your dates of travel to view options offering longer term stays. They feature all you need to make your extended getaway more comfortable like kitchens and yards. Some holiday homes might also offer weekly or monthly discounted prices, so you can have a longer stay for less.

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