Winsor Holiday Rentals

  • 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
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Winsor holiday rentals

Free WiFi

Apartment in Freemantle

Pebbles Guest House - Flat 7
2.0 star property
The price is S$103
includes taxes & fees
8 Mar - 9 Mar
Pebbles Guest House - Flat 7
Interior entrance

Aparthotel in Southampton City Centre

room2 Southampton Hometel
4.0 star property
9.4 out of 10, Exceptional, (1,201 reviews)
"Great location and vibe"
United Kingdom
Paul
The price is S$130
includes taxes & fees
8 Mar - 9 Mar
room2 Southampton Hometel
Premium bedding, Select Comfort beds, desk, laptop workspace

Aparthotel in Cowes

Pinnacle Suites
3.0 star property
9.8 out of 10, Exceptional, (26 reviews)
"Great place to stay. Facilities are very nice and clean. Zoe is a very helpful and kind host. "
Denmark
Sebastian
The price is S$199
includes taxes & fees
29 Mar - 30 Mar
Pinnacle Suites
Interior

Cottage in Ringwood

Little Timbers
3.0 star property
The price is S$491
includes taxes & fees
8 Mar - 9 Mar
Little Timbers
Marina

Residence in Bassett Green

Daisy Haven in Southampton
2.0 star property
The price is S$240
includes taxes & fees
12 Mar - 13 Mar
Daisy Haven in Southampton
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

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now
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

Rhinefield House Hotel

Rhinefield House Hotel

10/10 Excellent
"Staff, location"
James 2-night trip
Posted 2 days ago
Rhinefield House Hotel

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.