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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Winsor holiday rentals

Marina
Whitfield P10

Cottage in Yarmouth

Whitfield P10
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is Rp7.442.993
Rp8.931.591 total
includes taxes & fees
29 Dec - 30 Dec
Whitfield P10
House, Accessible, Ensuite (Farmhouse) | Exterior
Bridge Farmhouse

Villa in Salisbury

Bridge Farmhouse
4.0 star property
9.2 out of 10, Wonderful, (19)
"Staying here felt like you walked into a story book; beautiful gardens, bridge over the creek with swans swimming up and down, sheep in the fields, views of Salisbury Cathedral, stylish decorated rooms. We greatly enjoyed our stay. "
Canada
Jennifer E
The price is Rp34.780.713
Rp41.736.856 total
includes taxes & fees
9 Jan - 10 Jan 2026
Bridge Farmhouse
Luxury Apartment, Accessible, Private Bathroom | Terrace/patio
The Itchen River Apartments

Apartment in Southampton

The Itchen River Apartments
3.5 star property
10.0 out of 10, Exceptional, (1)
"Check-in was quite complicated but the support was good "
United Kingdom
Robert
The Itchen River Apartments
Apartment | 2 bedrooms, iron/ironing board, free WiFi, bed sheets
2 Bed Flat - Sleeps 4 - Parking - Wifi

Apartment in The Polygon

2 Bed Flat - Sleeps 4 - Parking - Wifi
3.0 star property
10.0 out of 10, Exceptional, (1)
"Great apartment, super friendly host!"
United Kingdom
Amy
The price is Rp2.980.155
Rp3.576.186 total
includes taxes & fees
28 Dec - 29 Dec
2 Bed Flat - Sleeps 4 - Parking - Wifi
Apartment, Balcony | Living area | Flat-screen TV
Southampton retreat-Hot Tub-Pool-Parking

Apartment in Shirley

Southampton retreat-Hot Tub-Pool-Parking
2.0 star property
7.0 out of 10, Good, (2)
"Serene location. Nice property. "
United Kingdom
Theertha
The price is Rp2.118.594
Rp3.220.263 total
includes taxes & fees
4 Jan - 5 Jan 2026
Southampton retreat-Hot Tub-Pool-Parking
Three Bedroom House | Living area | 40-inch Smart TV with digital channels, TV
Salisbury Residences by Charles Hope

Holiday Home in Salisbury

Salisbury Residences by Charles Hope
4.0 star property
Salisbury Residences by Charles Hope
Luxury Suite | Premium bedding, Select Comfort beds, desk, laptop workspace
Pinnacle Suites

Aparthotel in Cowes

Pinnacle Suites
3.0 star property
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 Rp2.937.783
Rp3.525.339 total
includes taxes & fees
28 Dec - 29 Dec
Pinnacle Suites
Deluxe Apartment | Living area | Flat-screen TV
Charles Hope Salisbury Centre

Apartment in Salisbury

Charles Hope Salisbury Centre
3.5 star property
9.6 out of 10, Exceptional, (4)
"Great location and well appointed apartment"
Australia
Greg
Charles Hope Salisbury Centre
Free WiFi
Pebbles Guest House - Flat 6

Apartment in Freemantle

Pebbles Guest House - Flat 6
2.0 star property
The price is Rp762.693
Rp915.232 total
includes taxes & fees
25 Dec - 26 Dec
Pebbles Guest House - Flat 6
Cottage | Living room
5 Yarmouth Cottages

Cottage in Freshwater

5 Yarmouth Cottages
3.5 star property
9.4 out of 10, Exceptional, (3)
"Convenient and spotlessly clean small cottage is a great base for exploring the IoW. Only slight downside is that the proximity to other guests means sitting outside can be a little bit of an exercise in hearing other people’s conversation! This small point aside, can recommend for a short stay. "
United Kingdom
Clive
The price is Rp6.208.921
Rp7.450.706 total
includes taxes & fees
28 Dec - 29 Dec
5 Yarmouth Cottages
Exclusive Apartment, Private Bathroom | Interior
4thedome

Apartment in New Milton

4thedome
3.5 star property
9.4 out of 10, Exceptional, (12)
"Had a lovely stay in this apartment . It was excellent. Very very clean and comfortable, with everything you could need and a lot of little extras. Just a couple of steps over to the clifftop in Barton on sea. Would definitely stay again."
United Kingdom
Stephen
The price is Rp1.525.387
Rp2.621.407 total
includes taxes & fees
6 Jan - 7 Jan 2026
4thedome
Exterior
Pamper House Holiday Home And Annex

Holiday Home in Ferndown

Pamper House Holiday Home And Annex
3.0 star property
Pamper House Holiday Home And Annex
House (3 Bedrooms) | Terrace/patio
Peaceful Elevated Residential Area - Walk to City

Cottage in Winchester

Peaceful Elevated Residential Area - Walk to City
5.0 star property
The price is Rp6.007.389
Rp7.208.867 total
includes taxes & fees
31 Dec - 1 Jan 2026
Peaceful Elevated Residential Area - Walk to City
Marina
Daisy Haven in Southampton

Residence in Bassett Green

Daisy Haven in Southampton
2.0 star property
The price is Rp3.610.083
Rp4.332.099 total
includes taxes & fees
28 Dec - 29 Dec
Daisy Haven in Southampton
Front of property
Peartree Serviced Apartments

Aparthotel in Salisbury

Peartree Serviced Apartments
3.5 star property
9.6 out of 10, Exceptional, (304)
"Enjoyable stay, handy to Salisbury landmarks."
Australia
Heather
The price is Rp1.724.694
Rp2.069.633 total
includes taxes & fees
11 Jan - 12 Jan 2026
Peartree Serviced Apartments
Apartment | Free WiFi
Pebbles Guest House - Flat 5

Apartment in Freemantle

Pebbles Guest House - Flat 5
2.0 star property
The price is Rp847.437
Rp1.016.924 total
includes taxes & fees
5 Jan - 6 Jan 2026
Pebbles Guest House - Flat 5
Free WiFi
Pebbles Guest House - Flat 7

Apartment in Freemantle

Pebbles Guest House - Flat 7
2.0 star property
The price is Rp1.016.924
Rp1.220.309 total
includes taxes & fees
25 Dec - 26 Dec
Pebbles Guest House - Flat 7
Balcony view
Southampton Serviced Apartment

Apartment in Bassett

Southampton Serviced Apartment
4.0 star property
8.4 out of 10, Very good, (179)
"Close to workplace. Nice heated apartment, has all the things you would need highly recommend. "
United Kingdom
Sheena
The price is Rp2.730.632
Rp3.276.758 total
includes taxes & fees
5 Jan - 6 Jan 2026
Southampton Serviced Apartment
Interior entrance
room2 Southampton Hometel

Aparthotel in Southampton City Centre

room2 Southampton Hometel
4.0 star property
9.4 out of 10, Exceptional, (1179)
"Staff was great and the room was really nice. I was impressed by the design and it was spacious "
United States
Vanessa
The price is Rp1.418.766
Rp1.702.520 total
includes taxes & fees
26 Dec - 27 Dec
room2 Southampton Hometel
Marina
High Tide

Cottage in Cowes

High Tide
3.0 star property
The price is Rp10.933.101
Rp13.119.721 total
includes taxes & fees
5 Jan - 6 Jan 2026
High Tide
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

Novotel Southampton

Novotel Southampton

10/10 Excellent
"Convenient for the Cruise terminal. We got a short taxi from the hotel to the Terminal. Easy walking from the hotel to restaurants and shops. Nice gym and nice hotel"
Neelima 1-night trip
Posted 1 day ago
Novotel Southampton

Find out more about Winsor

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

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  • Enter your travel dates to view the best deals on holiday rentals in Winsor while they last

Look no further and take a look at our great range of rental properties in Winsor!

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.