Winsor Vacation 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
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Winsor vacation rentals

Deluxe Studio | Iron/ironing board, free WiFi

Settle Southampton

Settle Southampton
Freemantle
10.0 out of 10, Exceptional, (2 reviews)
"I had trouble getting in so I messaged and received a response very quickly Good location Clean room"
United Kingdom
elysha
The price is NT$1,734
NT$4,008 total
includes taxes & fees
May 25 - May 26
Settle Southampton
Double Room | Iron/ironing board, free WiFi

Settle Winchester

Settle Winchester
2.0 star property
Winchester
The price is NT$1,670
NT$5,216 total
includes taxes & fees
Jun 7 - Jun 8
Settle Winchester
Interior entrance

room2 Southampton Hometel

room2 Southampton Hometel
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,213 reviews)
"Friendly staff - great breakfast food options "
United Kingdom
Christian
The price is NT$3,204
NT$3,845 total
includes taxes & fees
May 18 - May 19
room2 Southampton Hometel
Living area

Cape 12,

Cape 12,
2.0 star property
Yarmouth
The price is NT$12,777
NT$15,332 total
includes taxes & fees
May 15 - May 16
Cape 12,
Exclusive Apartment, Private Bathroom | Interior

4thedome

4thedome
3.5 star property
New Milton
9.4 out of 10, Exceptional, (12 reviews)
"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 NT$4,283
NT$6,638 total
includes taxes & fees
May 13 - May 14
4thedome
Deluxe Suite | Premium bedding, Select Comfort beds, desk, laptop workspace

Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.8 out of 10, Exceptional, (27 reviews)
"No air conditioning but there was a dyson fan and a heater. Room had a coffee machine, mini fridge, hairdryer and a handheld steamer. We stayed in a room overlooking the harbour and it was very quiet. You couldn't hear any noise from the pub next door. Room was modern and very clean. The bed was huge (king) and very comfortable. There were places nearby to get breakfast and is very close to a Sainsbury and M&S food (Apr26)."
United Kingdom
Victoria
The price is NT$4,961
NT$5,953 total
includes taxes & fees
May 12 - May 13
Pinnacle Suites
Exterior

The South Coast Snug

The South Coast Snug
2.0 star property
Fareham
10.0 out of 10, Exceptional, (1 review)
"Lovely appartment.very welcoming, clean and tidy, all equipment was their to use for a pleasant stay.very quiet.would highly reccomend"
United Kingdom
Ian
The price is NT$2,893
NT$3,471 total
includes taxes & fees
May 28 - May 29
The South Coast Snug
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

Harbour Hub Hotel

Harbour Hub Hotel

4/10 Poor
"Could not enter the building in the pre planned way."
Ray 1-night trip
Posted 3 hours ago
Harbour Hub Hotel

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 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.