Winsor Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Winsor holiday rentals

Front of property
room2 Southampton Hometel

room2 Southampton Hometel

room2 Southampton Hometel
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1173)
"Welcoming staff, clean rooms, cosy reception area, nicely decorated rooms and amenities. Chic bar/cafe/food and work area. Was perfect for my trip, close to the docks and centre of Southampton for tours, shopping and history."
United States
Fiona
The price is HK$651
HK$781 total
includes taxes & fees
31 Dec - 1 Jan 2026
room2 Southampton Hometel
Private kitchen
Peartree Serviced Apartments

Peartree Serviced Apartments

Peartree Serviced Apartments
3.5 star property
Salisbury
9.6 out of 10, Exceptional, (301)
"Enjoyable stay, handy to Salisbury landmarks."
Australia
Heather
The price is HK$760
HK$913 total
includes taxes & fees
4 Jan - 5 Jan 2026
Peartree Serviced Apartments
Marina
Daisy Haven in Southampton

Daisy Haven in Southampton

Daisy Haven in Southampton
2.0 star property
Bassett Green
The price is HK$1,436
HK$1,724 total
includes taxes & fees
21 Dec - 22 Dec
Daisy Haven in Southampton
Premium bedding, Select Comfort beds, desk, laptop workspace
Pinnacle Suites

Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.8 out of 10, Exceptional, (25)
"Great place to stay. Facilities are very nice and clean. Zoe is a very helpful and kind host. "
Denmark
Sebastian
The price is HK$1,353
HK$1,624 total
includes taxes & fees
23 Dec - 24 Dec
Pinnacle Suites
Private kitchen
2 Bed Flat - Sleeps 4 - Parking - Wifi

2 Bed Flat - Sleeps 4 - Parking - Wifi

2 Bed Flat - Sleeps 4 - Parking - Wifi
3.0 star property
The Polygon
10.0 out of 10, Exceptional, (1)
"Great apartment, super friendly host!"
United Kingdom
Amy
The price is HK$1,359
HK$1,631 total
includes taxes & fees
21 Dec - 22 Dec
2 Bed Flat - Sleeps 4 - Parking - Wifi
Exterior
The Cliff House Hotel

The Cliff House Hotel

The Cliff House Hotel
4.0 star property
New Milton
9.4 out of 10, Exceptional, (403)
"Great location, food, accomodation and pleasant staff."
United Kingdom
Anthony
The price is HK$1,119
HK$1,343 total
includes taxes & fees
14 Dec - 15 Dec
The Cliff House Hotel
Shared kitchen
Bayview Apartments

Bayview Apartments

Bayview Apartments
2.0 star property
Southampton City Centre
8.0 out of 10, Very good, (3)
"To be honest although the apartment was really nice we didn’t have hardly any knives and forks and spoons for 5 people, the fridge was filthy and the cooking equipment was old worn out and filthy. For nearly £300 for one night we expected better "
United Kingdom
Derek
The price is HK$2,429
HK$2,914 total
includes taxes & fees
20 Dec - 21 Dec
Bayview Apartments
Balcony view
Southampton Serviced Apartment

Southampton Serviced Apartment

Southampton Serviced Apartment
4.0 star property
Bassett
8.4 out of 10, Very good, (178)
"Close to workplace. Nice heated apartment, has all the things you would need highly recommend. "
United Kingdom
Sheena
The price is HK$1,279
HK$1,535 total
includes taxes & fees
15 Dec - 16 Dec
Southampton Serviced Apartment
Fridge, microwave, oven, dishwasher
Beautiful 2 bedroom full-furnished semi-detached house with parking

Beautiful 2 bedroom full-furnished semi-detached house with parking

Beautiful 2 bedroom full-furnished semi-detached house with parking
Dibden Purlieu
9.4 out of 10, Exceptional, (6)
"Great location, xxx"
United Kingdom
Christopher K.
The price is HK$1,311
HK$1,499 total
includes taxes & fees
16 Dec - 17 Dec
Beautiful 2 bedroom full-furnished semi-detached house with parking
Outdoor pool, a heated pool
Luxury villa, amazing location, pool, jacuzzi, snooker, cinema & tennis court!

Luxury villa, amazing location, pool, jacuzzi, snooker, cinema & tennis court!

Luxury villa, amazing location, pool, jacuzzi, snooker, cinema & tennis court!
Ringwood
10.0 out of 10, Exceptional, (51)
"Lovely property, great communications and support during our stay. Pool and hot tub facilities excellent. Recommended!!"
United Kingdom
Satnam D.
Luxury villa, amazing location, pool, jacuzzi, snooker, cinema & tennis court!
Fridge, dishwasher, electric kettle, cookware/dishes/utensils
Bailey Cottage

Bailey Cottage

Bailey Cottage
3.0 star property
Southampton
The price is HK$12,664
HK$15,196 total
includes taxes & fees
17 Dec - 18 Dec
Bailey Cottage
Marina
Superyacht on 5* Town Quay Marina, Southampton

Superyacht on 5* Town Quay Marina, Southampton

Superyacht on 5* Town Quay Marina, Southampton
Southampton City Centre
9.6 out of 10, Exceptional, (9)
"The yacht Ohana is a great place to stay with excellent facilities and in a fab location close to bars and restaurants.A very helpful owner made our weekend perfect! "
United States
Helen D.
The price is HK$2,239
HK$3,009 total
includes taxes & fees
14 Dec - 15 Dec
Superyacht on 5* Town Quay Marina, Southampton
Fridge, microwave, oven, coffee/tea maker
Adorable 2-bedroom apartment in Southampton

Adorable 2-bedroom apartment in Southampton

Adorable 2-bedroom apartment in Southampton
Freemantle
10.0 out of 10, Exceptional, (1)
"We had a great shopping weekend staying at this apartment. The host was super friendly and easy to contact. The property was very sweet, really clean and we felt safe. Access was easy. Parking was good. I really have no complaints. We would not hesitate to stay here again. The host was one of the best we’ve ever had and it was lovely to see the property was well cared for and thoughtfully stocked with little extras like tea coffee and the odd spirit in the bar! I wouldn’t really want to walk...
United Kingdom
Lucy
The price is HK$824
HK$1,199 total
includes taxes & fees
15 Dec - 16 Dec
Adorable 2-bedroom apartment in Southampton
Interior
Karelia - Lovely Log Cabin w/Hot-tub and forest access, sleeps 10

Karelia - Lovely Log Cabin w/Hot-tub and forest access, sleeps 10

Karelia - Lovely Log Cabin w/Hot-tub and forest access, sleeps 10
Ashley Heath
9.8 out of 10, Exceptional, (152)
"Great for large family, easy access to forest walks and close enough for short drive to beaches. Lovely large hot tub and excellent bathrooms."
United Kingdom
John H.
Karelia - Lovely Log Cabin w/Hot-tub and forest access, sleeps 10
Private kitchen
19 Quayside Walk

19 Quayside Walk

19 Quayside Walk
3.5 star property
Southampton
The price is HK$5,204
HK$6,244 total
includes taxes & fees
20 Dec - 21 Dec
19 Quayside Walk
Interior
Aquanaut

Aquanaut

Aquanaut
3.5 star property
Cowes
The price is HK$27,727
HK$33,272 total
includes taxes & fees
19 Dec - 20 Dec
Aquanaut
Living area
Charles Hope Salisbury Centre

Charles Hope Salisbury Centre

Charles Hope Salisbury Centre
3.5 star property
Salisbury
9.6 out of 10, Exceptional, (4)
"Great location and well appointed apartment"
Australia
Greg
Charles Hope Salisbury Centre
Exterior
New Forest cliff top apartment with distant view of the Needles

New Forest cliff top apartment with distant view of the Needles

New Forest cliff top apartment with distant view of the Needles
Barton on Sea
9.6 out of 10, Exceptional, (171)
"Lovely clean compact apartment in great sea front location. Enjoyed our stay many thanks great hosts. "
United Kingdom
Anonymous traveller
New Forest cliff top apartment with distant view of the Needles
Private kitchen
Family House in Eastleigh

Family House in Eastleigh

Family House in Eastleigh
2.0 star property
Eastleigh
Family House in Eastleigh
Fridge, microwave, oven, stovetop
Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!

Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!

Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!
Three Legged Cross
9.8 out of 10, Exceptional, (191)
"The facilities offered by the Thatched Cottage are excellent. The pool area was fantastic and much enjoyed by the whole of our 3 generation family. The house was huge and there were plenty of areas around the property to sit and relax and eat together."
United Kingdom
Lindsay S.
Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!
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.
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Top Winsor Hotel Reviews

The Star Hotel

The Star Hotel

10/10 Excellent
"All very good "
Jin Gei 2-night trip
Posted 2 days ago
The Star Hotel

Find out more about Winsor

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Frequently asked questions

Are there holiday rentals in Winsor?

Yes, there are holiday rentals close to the most popular sights in Winsor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winsor has to offer?

The Cliff House Hotel: This holiday home rental outside of Winsor offers a terrace, a garden and daily housekeeping to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

What can I see and do in Winsor?

While exploring the area, visit family-friendly sights like Paultons Family Theme Park - Home of Peppa Pig World, or get outside and enjoy nature at New Forest National Park. Southampton Cruise Terminal and New Forest Wildlife Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Winsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winsor. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family gatherings.