Winchester Holiday Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide

Find properties with these dates

Tonight
May 11 - May 12
Tomorrow
May 12 - May 13
Next weekend
May 17 - May 19

Holiday Rentals in Winchester

Flat-screen TV
Two Bare Feet
3.5 star property
9.2 out of 10, Wonderful, (32)
"Beautiful property with every thing you could need. Complimentary eggs butter milk bread and fruit a lovely touch and very welcome. We would highly recommend 2 bare feet. Short walk into the town centre. Absolutely perfect. 5 star."
The price is AU$185
per night
12 May - 13 May
Two Bare Feet
Exterior
Beautifully Converted 17th C Grade II Stables/Coach House/Barn In Quiet Location
9.8 out of 10, Exceptional, (139)
"My wife and I enjoyed our stay. We enjoyed Twyford and nearby Winchester the most during our holiday. The barn is also well positioned to a wonderful trail head. We traveled all over southern England from the barn. We highly recommend."
Beautifully Converted 17th C Grade II Stables/Coach House/Barn In Quiet Location
Front of property
room2 Southampton Hometel
4.0 star property
9.6 out of 10, Exceptional, (770)
"Really enjoyed this place, nice to have your own kitchenette, friendly staff and lovely spacious rooms ! Only downside, not much of a sound barrier, 6am baby crying and its parents talking extremely loudly to it, not an issue since already awake but something to keep in mind. "
The price is AU$218
per night
19 May - 20 May
room2 Southampton Hometel
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Studio, 1 Queen Bed | Private kitchen
Peartree Serviced Apartments
3.5 star property
9.6 out of 10, Exceptional, (218)
"Lovely apartment with a continental breakfast in the kitchen when we arrived, Didn’t see any of the reception staff as we did self check in and key drop off, We would definitely stay here again "
The price is AU$252
per night
3 June - 4 June
Peartree Serviced Apartments
Children's play area - outdoor
Mill Rythe Coastal Village
2.0 star property
9.2 out of 10, Wonderful, (31)
"Great holiday park- very well maintained and friendly, good activities for kids. Nice area, lovely accomodation. Preferred to eat out. "
Mill Rythe Coastal Village
Dining
Southsea Stays
8.0 out of 10, Very good, (4)
"Just a stop over for a wedding, host was very hellful when I realised I made a mistake on the booking and sorted for me without any hassle "
The price is AU$119
per night
13 May - 14 May
Southsea Stays
View from room
Southampton Serviced Apartment
4.0 star property
8.4 out of 10, Very good, (148)
"Comfortable apartment with lift and free parking "
Southampton Serviced Apartment
Superior Double Room, Shared Bathroom
Portsmouth Stays
2.0 star property
10.0 out of 10, Exceptional, (1)
"I have enjoyed my short stay at the property, newly refurbished, clean and a luxurious bathroom and lounge/dining area. Kettle would do better with a descaling though. Surrounding area very poor but overall safe."
The price is AU$121
per night
15 May - 16 May
Portsmouth Stays
Beach
Idyllic cottage in the heart of the New Forest National Park
9.8 out of 10, Exceptional, (178)
"A lovely feeling as soon as you walk in the door. A very welcoming, comfortable and pristine house. Great, secure garden and a perfect location, 5 minutes walk from Burley village where you’ll find a lovely village store, pubs, gift shops and cafes. Great for forest walks. Our Springer had a permanent grin on during our stay!"
Idyllic cottage in the heart of the New Forest National Park
Cottage, 1 Bedroom (Dormouse) | Terrace/patio
Hazelhurst Farm
4.5 star property
9.6 out of 10, Exceptional, (45)
"We had a great family stay at Hazelhurst Farm. The cottage is absolutely beautiful and fully equipped with everything we needed. The hosts (Hayley and Carl) were also super nice and helpful. We'll definitely come back "
Hazelhurst Farm
Beach nearby
'The Haven' a luxury apartment close to the Meon Shore coast.
10.0 out of 10, Exceptional, (199)
"It is a lovely property. We are able to park outside and as soon as you walk in a lovely smell and so clean, warm and welcoming. It is ideal for us as family and friends are just around the corner and the hosts are lovely too."
'The Haven' a luxury apartment close to the Meon Shore coast.
Apartment | Private kitchen
Charles Hope Apartments Southampton
3.5 star property
5.8 out of 10, (6)
"The apartment is in a great location and the info you receive is thorough. Make sure you ask for parking though as it is limited. The apartment was very clean. Our door lock came loose and they helped us within 30 minutes which was really good. The only negatives were that the windows are so thin in places you can hear the traffic and the mattresses were a bit firm for us but if we were in Southampton we would definitely book here again. Great customer service and the space is perfect. "
The price is AU$276
per night
13 May - 14 May
Charles Hope Apartments Southampton
Beach nearby, sun-loungers
MANSION WITH SWIMMING POOL, GAMES ROOM, SEA VIEWS, SANDY BEACHES 2 MINS WALK
9.8 out of 10, Exceptional, (58)
"We had an incredible stay here. We got lucky with the weather but the house was more than big enough for our party of 16. It was clean and tidy with great cooking facilities and the pool was lovely in 30 degrees! The owners were amazing with great communication in the run up to and during the stay and very helpful with check in. I would definitely stay here again and would highly reccomend it."
MANSION WITH SWIMMING POOL, GAMES ROOM, SEA VIEWS, SANDY BEACHES 2 MINS WALK
Deluxe Room, 1 King Bed
Pinnacle Suites
3.0 star property
Pinnacle Suites
Fridge, microwave, oven, stovetop
An Idyllic, Family- Friendly Cottage On A Private Estate In Burley
10.0 out of 10, Exceptional, (52)
"aaa"
An Idyllic, Family- Friendly Cottage On A Private Estate In Burley
Flat-screen TV
Southampton Waterside by Charles Hope
3.0 star property
6.0 out of 10, (2)
"I arrived and the boiler was not working. They weren't able to help. (they don't have anybody on site of the property ever. I had to try myself.) I then had to wait for 5 DAYS expecting and being told each day that an engineer would come to fix it. Nobody ever came. Whilst I had to wait in the apartment throughout that time for somebody to come, expecting someone to. But they kept breaking their word. I've honestly never met a company less bothered about their property not having working heating...
The price is AU$257
per night
12 May - 13 May
Southampton Waterside by Charles Hope
Property grounds
Yacht ‘X’ - 44 foot modern yacht on 5 star Marina
10.0 out of 10, Exceptional, (2)
"Great place to stay, space is so well thought out and the handover is so informative. Local knowledge of area also advised which is really helpful. Would definitely stay again"
The price is AU$469
per night
12 May - 13 May
Yacht ‘X’ - 44 foot modern yacht on 5 star Marina
Beach nearby
Cowes retreat
9.8 out of 10, Exceptional, (6)
"Great location which suited us perfectly."
Cowes retreat
Smart TV, stereo
Superyacht on 5* Ocean Village Marina, Southampton
The price is AU$607
per night
15 May - 16 May
Superyacht on 5* Ocean Village Marina, Southampton
Tranquil Cottage in this Quiet Corner of The New Forest.
9.8 out of 10, Exceptional, (232)
"A lovely property with a secure garden for my dog and access to the owner’s garden where you can meet Tilly the friendly black lab. Richard was an exceptional host and came to say hello after check in. The location is great. Down a very quiet country lane but close to both the New Forest and the Solent."
Tranquil Cottage in this Quiet Corner of The New Forest.
Don't see what you're looking for?
See all available properties in Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Winchester Holiday Home Travel Info

Number of holiday homes
17
Popular accommodation
Winchester private holiday homes
Known landmarks
Winchester Cathedral, Marwell Zoo and Winchester Science Centre and Planetarium

Other types of properties in Winchester you may be interested in

Exterior
The Winchester Hotel & Spa
4.0 star property
8.2 out of 10, Very good, (1000)
"Lovely clean well kept hotel"
The price is AU$192
per night
16 May - 17 May
The Winchester Hotel & Spa
Lobby sitting area
Norton Park Hotel, Spa & Manor House
4.0 star property
8.0 out of 10, Very good, (1001)
"Lovely staff very helpful was there for a family wedding "
The price is AU$162
per night
19 May - 20 May
Norton Park Hotel, Spa & Manor House
Daily buffet breakfast for a fee
Winchester Royal Hotel
4.0 star property
8.2 out of 10, Very good, (1003)
"Central position"
The price is AU$160
per night
9 June - 10 June
Winchester Royal Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as AU$119 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Winchester Science Centre and Planetarium, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the stunning cathedral and picturesque gardens in Winchester. The array of shops and festivals are some other things you might want to check out while you're here.

How many holiday rentals are there in Winchester?

Expedia has 41 holiday rentals for your stay in Winchester.

What’s there to see and do in Winchester?

Winchester Science Centre and Planetarium and Marwell Zoo are a couple of the family-friendly sights, whereas cultural attractions include Great Hall and Jane Austen's House. While in the area, you can also visit popular places such as Southampton Cruise Terminal and Paultons Family Theme Park - Home of Peppa Pig World.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.

Recent reviews of Winchester properties
Expedia verified reviews

Leonardo Royal Southampton Grand Harbour

Leonardo Royal Southampton Grand Harbour

5/5 Excellent
"Straight forward to find. Easy walking distance to ports and town centre. Good choice of food on menu. "
A verified traveller stayed at Leonardo Royal Southampton Grand Harbour
Posted 14 hours ago
Leonardo Royal Southampton Grand Harbour