Winsor Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation 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, (1159)
"staff was very friendly and rooms we clean and comfortable "
Canada
Kathy
The price is P5,234
P6,281 total
includes taxes & fees
Nov 23 - Nov 24
room2 Southampton Hometel
Private kitchen
Stonehenge Cottages

Stonehenge Cottages

5.0 star property
Salisbury
9.8 out of 10, Exceptional, (105)
"The property is beautifully designed. It is compact but well planned out and very tasteful. Everything you need is there. The breakfast basket is delightful! The cottage is attractive and in a lovely location. It is so easy to just walk across the road for dinner. We loved it!!"
United States
ian
The price is P11,603
P13,924 total
includes taxes & fees
Nov 17 - Nov 18
Stonehenge Cottages
Private kitchen
Peartree Serviced Apartments

Peartree Serviced Apartments

3.5 star property
Salisbury
9.6 out of 10, Exceptional, (295)
"The place was right around the corner of rail station, so easy to get to. Was quiet for being so near to railway. The free laundry set up was very convenient; even provided detergent. Would stay there again. Thank you."
United States
Brenda
The price is P5,975
P7,169 total
includes taxes & fees
Dec 14 - Dec 15
Peartree Serviced Apartments
Dining
The Itchen River Apartments

The Itchen River Apartments

4.0 star property
Southampton
10.0 out of 10, Exceptional, (1)
"Check-in was quite complicated but the support was good "
United Kingdom
Robert
The price is P7,779
P14,001 total
includes taxes & fees
Nov 22 - Nov 23
The Itchen River Apartments
Interior
5 Yarmouth Cottages

5 Yarmouth Cottages

3.5 star property
Freshwater
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 P20,872
P25,047 total
includes taxes & fees
Nov 22 - Nov 23
5 Yarmouth Cottages
Living area
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
1 bedroom, premium bedding, Select Comfort beds, desk
Pinnacle Suites

Pinnacle Suites

3.0 star property
Cowes
9.8 out of 10, Exceptional, (25)
"Had a great time here, in town for a wedding. The location is perfect and right off the red jet ferry. Zoe was also super helpful "
Canada
Andre
The price is P10,112
P12,135 total
includes taxes & fees
Nov 17 - Nov 18
Pinnacle Suites
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 P8,103
P9,723 total
includes taxes & fees
Nov 17 - Nov 18
The Cliff House Hotel
Marina
Whitfield P10

Whitfield P10

3.0 star property
Yarmouth
10.0 out of 10, Exceptional, (1)
The price is P25,021
P30,025 total
includes taxes & fees
Nov 20 - Nov 21
Whitfield P10
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winsor Hotel Reviews

Leonardo Royal Southampton Grand Harbour

Leonardo Royal Southampton Grand Harbour

10/10 Excellent
"Lovely hotel experience all around. Wonderful front desk personnel, very nice bar with excellent service "
Susan 1-night trip
Posted 1 day ago
Leonardo Royal Southampton Grand Harbour

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!

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Winsor?

Yes, we give you a choice of vacation rentals close to the most popular sights in Winsor, or you can select a more remote option if you're looking for relaxation.

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

The Cliff House Hotel: Visitors like this Winsor vacation home rental. It offers a terrace, a garden, and daily housekeeping to help you feel perfectly comfortable in your new surroundings. This vacation 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 larger area.

What are vacation rentals like in Winsor?

Vacation rentals are private properties you can book for several days or longer in Winsor. Vacation rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a small group gathering.