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Check prices for these dates

Tonight
19 Dec - 20 Dec
Tomorrow
20 Dec - 21 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Winsor holiday rentals

Studio, 1 Queen Bed | Private kitchen | Fridge, microwave, stovetop, dishwasher
Peartree Serviced Apartments

Aparthotel in Salisbury

Peartree Serviced Apartments
3.5 star property
9.6 out of 10, Exceptional, (302)
"Enjoyable stay, handy to Salisbury landmarks."
Australia
Heather
The price is ฿3,265
฿3,918 total
includes taxes & fees
4 Jan - 5 Jan 2026
Peartree Serviced Apartments
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 ฿2,840
฿4,881 total
includes taxes & fees
8 Jan - 9 Jan 2026
4thedome
Front of property
room2 Southampton Hometel

Aparthotel in Southampton City Centre

room2 Southampton Hometel
4.0 star property
9.4 out of 10, Exceptional, (1176)
"staff was very friendly and rooms we clean and comfortable "
Canada
Kathy
The price is ฿2,608
฿3,130 total
includes taxes & fees
22 Dec - 23 Dec
room2 Southampton Hometel
Free WiFi
Pebbles Guest House - Flat 6

Apartment in Freemantle

Pebbles Guest House - Flat 6
2.0 star property
The price is ฿1,420
฿1,704 total
includes taxes & fees
20 Dec - 21 Dec
Pebbles Guest House - Flat 6
Family 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
Exterior
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 ฿3,945
฿5,996 total
includes taxes & fees
4 Jan - 5 Jan 2026
Southampton retreat-Hot Tub-Pool-Parking
Deluxe Room, 1 Double Bed, Harbour View | 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 ฿5,470
฿6,564 total
includes taxes & fees
20 Dec - 21 Dec
Pinnacle Suites
Cottage | Interior
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 ฿11,516
฿13,819 total
includes taxes & fees
23 Dec - 24 Dec
5 Yarmouth Cottages
Free WiFi
Pebbles Guest House - Flat 7

Apartment in Freemantle

Pebbles Guest House - Flat 7
2.0 star property
The price is ฿1,893
฿2,272 total
includes taxes & fees
20 Dec - 21 Dec
Pebbles Guest House - Flat 7
Apartment | Private kitchen | Fridge, microwave, oven, stovetop
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 ฿5,556
฿6,667 total
includes taxes & fees
28 Dec - 29 Dec
2 Bed Flat - Sleeps 4 - Parking - Wifi
Apartment | Free WiFi
Pebbles Guest House - Flat 5

Apartment in Freemantle

Pebbles Guest House - Flat 5
2.0 star property
Pebbles Guest House - Flat 5
Exterior
The Cliff House Hotel

Holiday Home in New Milton

The Cliff House Hotel
4.0 star property
9.4 out of 10, Exceptional, (403)
"Great location, food, accomodation and pleasant staff."
United Kingdom
Anthony
The price is ฿5,961
฿7,153 total
includes taxes & fees
22 Dec - 23 Dec
The Cliff House Hotel
Balcony view
Southampton Serviced Apartment

Apartment in Bassett

Southampton Serviced Apartment
4.0 star property
8.4 out of 10, Very good, (178)
"Ideal, close to Univeristy. "
United Kingdom
Sheena
The price is ฿5,224
฿6,269 total
includes taxes & fees
4 Jan - 5 Jan 2026
Southampton Serviced Apartment
Marina
Whitfield P10

Cottage in Yarmouth

Whitfield P10
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is ฿13,805
฿16,566 total
includes taxes & fees
23 Dec - 24 Dec
Whitfield P10
Exterior
Salisbury Residences by Charles Hope

Holiday Home in Salisbury

Salisbury Residences by Charles Hope
4.0 star property
Salisbury Residences by Charles Hope
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 ฿11,185
฿13,422 total
includes taxes & fees
31 Dec - 1 Jan 2026
Peaceful Elevated Residential Area - Walk to City
House, Ensuite | Exterior
The Cheese House

Cottage in Salisbury

The Cheese House
3.0 star property
10.0 out of 10, Exceptional, (1)
"Loved this house. Beautiful spaces, lots of room, all modern updates with rustic farm feel. Gorgeous property."
United States
Bobby
The price is ฿65,566
฿78,680 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Cheese House
Luxury House | 6 bedrooms, Egyptian cotton sheets, premium bedding, Select Comfort beds
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
Marina
Daisy Haven in Southampton

Residence in Bassett Green

Daisy Haven in Southampton
2.0 star property
The price is ฿5,975
฿7,170 total
includes taxes & fees
21 Dec - 22 Dec
Daisy Haven in Southampton
Luxury Suite, Ensuite | Private kitchen
Stonehenge Cottages

Cottage in Salisbury

Stonehenge Cottages
5.0 star property
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 ฿6,627
฿7,952 total
includes taxes & fees
4 Jan - 5 Jan 2026
Stonehenge Cottages
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

voco Winchester Hotel & Spa by IHG

voco Winchester Hotel & Spa by IHG

10/10 Excellent
"Staff very helpful. Food good at the hotel"
Callum 3-night trip
Posted 1 day ago
voco Winchester Hotel & Spa by IHG

Find out more about Winsor

Search for holiday rentals in Winsor on Expedia! 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
  • 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.