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Check prices for these dates

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Top Holiday Rentals in Winsor

Front of property
room2 Southampton Hometel

room2 Southampton Hometel

4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1171)
"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 ₹7,311
₹8,774 total
includes taxes & fees
1 Jan - 2 Jan 2026
room2 Southampton Hometel
Luxury Suite, Ensuite | Private kitchen
Stonehenge Cottages

Stonehenge Cottages

5.0 star property
Salisbury
9.8 out of 10, Exceptional, (105)
"Information, including a video, provided by the friendly owners before and during our stay was excellent. The beautifully appointed cottage was convenient for Salisbury and for the nearby pub which serves good food. We will definitely stay there again, if in the area."
United Kingdom
Fiona
The price is ₹16,892
₹20,270 total
includes taxes & fees
9 Dec - 10 Dec
Stonehenge Cottages
Deluxe Room, 1 Double Bed, Harbour View | Premium bedding, Select Comfort beds, desk, laptop workspace
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 ₹15,592
₹18,711 total
includes taxes & fees
9 Dec - 10 Dec
Pinnacle Suites
Studio, 1 Queen Bed | Private kitchen | Fridge, microwave, stovetop, dishwasher
Peartree Serviced Apartments

Peartree Serviced Apartments

3.5 star property
Salisbury
9.6 out of 10, Exceptional, (299)
"Enjoyable stay, handy to Salisbury landmarks."
Australia
Heather
The price is ₹9,029
₹10,834 total
includes taxes & fees
4 Jan - 5 Jan 2026
Peartree Serviced Apartments
Beach nearby
The Well House

The Well House

3.0 star property
Bournemouth
The price is ₹206,201
₹247,440 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Well House
Exterior
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 ₹16,992
₹20,390 total
includes taxes & fees
22 Dec - 23 Dec
The Cliff House Hotel
Apartment | Private kitchen | Fridge, microwave, oven, stovetop
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 ₹28,709
₹34,450 total
includes taxes & fees
11 Dec - 12 Dec
2 Bed Flat - Sleeps 4 - Parking - Wifi
Cottage | Interior
4 Holt Court

4 Holt Court

3.0 star property
Salisbury
9.0 out of 10, Wonderful, (2)
"Fabulous location within easy walking distance of the key shops, restaurants, and cathedral, parks etc. Amazing property which is well equipped too. Only downside for us was some minor dirty bits that had been missed off on the cleaning schedule, and the welcome pack needs updating e.g. WiFi was different, and this didn;t include instructions/code for the bin stores (that was on the back of the front door). Would be helpful to have everything in one place. However, that didn't spoil an...
United Kingdom
Karl
The price is ₹124,020
₹124,020 total
includes taxes & fees
12 Dec - 13 Dec
4 Holt Court
Family Apartment | Living area | Flat-screen TV
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
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

Leonardo Royal Southampton Grand Harbour

Leonardo Royal Southampton Grand Harbour

10/10 Excellent
"Hotel is very clean, facilities are great and all staff very friendly. The perfect 4 star experience. "
Matthew 1-night trip
Posted 13 hours ago
Leonardo Royal Southampton Grand Harbour

Find out more about Winsor

Holiday Rentals in Winsor

Search for holiday rentals in Winsor on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Winsor using one of the methods below:

  • View our selection of featured holiday rentals in Winsor
  • Use the map to find apartments and other holiday homes in the Winsor neighbourhood you prefer
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Look no further and take a look at our great range of rental properties in 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.