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Winsor Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winsor holiday rentals

A modern interior with a red sofa, black chairs, and a patterned floor.

1. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,355 reviews)
"Great location and friendly staff!"
United States
Gary
The price is S$119
includes taxes & fees
13 Nov - 14 Nov
Second Nature Southampton
A bedroom with a large bed, a wooden ceiling, and a view of a brick building outside.

2. Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.0 out of 10, Very good, (12 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is S$185
includes taxes & fees
9 Nov - 10 Nov
Settle Southampton
A corner room with a large window overlooking a city street and buildings.

3. Ocean Quay Luxury - Stylish 2 Bed - Has Parking

Ocean Quay Luxury - Stylish 2 Bed - Has Parking
3.0 star property
Southampton City Centre
Ocean Quay Luxury - Stylish 2 Bed - Has Parking
A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a radiator.

4. Settle Winchester

Settle Winchester
2.0 star property
Winchester City Center
The price is S$154
includes taxes & fees
8 Nov - 9 Nov
Settle Winchester
A bedroom with a large bed, a sofa, a TV, and a window with blinds.

5. QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
5.8 out of 10, (17 reviews)
"They sent me an email at the last minute saying that it was double booked and they canceled my reservation that was already prepaid"
United States
kia
The price is S$311
includes taxes & fees
14 Oct - 15 Oct
QE2 Loft Apartments
A modern living room with a sofa, ottoman, and a coffee table with flowers. There is a fireplace, a television, and a kitchen area visible.

6. 7 Wild Haven

7 Wild Haven
3.0 star property
Salisbury
The price is S$885
includes taxes & fees
1 Nov - 2 Nov
7 Wild Haven
A room with a dartboard, a power outlet, a potted plant, and a curtain.

7. 4 Bedrooms - The Family Haven With Parking Near Airport

4 Bedrooms - The Family Haven With Parking Near Airport
3.0 star property
Eastleigh
The price is S$271
includes taxes & fees
1 Nov - 2 Nov
4 Bedrooms - The Family Haven With Parking Near Airport
A sign for Hotel Peartree, a serviced apartment, with contact information and website.

8. Peartree Serviced Apartments

Peartree Serviced Apartments
3.5 star property
Salisbury
9.6 out of 10, Exceptional, (327 reviews)
"Great. They have everything you could need - well appointed kitchen, milk and breakfast provided, plenty of fluffy towels even down to non stick bath mats"
Australia
Stephanie
The price is S$176
includes taxes & fees
8 Nov - 9 Nov
Peartree Serviced Apartments
A modern kitchen with a built-in island, a sink, and a clock on the wall.

9. 4thedome

4thedome
3.5 star property
New Milton
9.4 out of 10, Exceptional, (13 reviews)
"Lovely peaceful location just around the corner from the beach. Small shop, cafes and bar near by, we’d recommend a visit to the ice cream parlour - lots of flavours with vegan and doggy options. The accommodation was spotlessly clean, comfortable and well equipped. Check-in was seamless and the host responded quickly to all communications. Only downside was no enclosed outside space for our dogs"
United Kingdom
Ceri
The price is S$228
includes taxes & fees
4 Nov - 5 Nov
4thedome
A narrow stream with clear water, surrounded by lush greenery and wildflowers.

10. Roslyn

Roslyn
2.0 star property
Romsey
The price is S$875
includes taxes & fees
20 Oct - 21 Oct
Roslyn
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

Leonardo Royal Southampton Grand Harbour

Leonardo Royal Southampton Grand Harbour

10/10 Excellent
"Large room balcony very clean. Lovely staff. Leo's place good food"
Patricia 1-night trip
Posted 4 hours ago
Leonardo Royal Southampton Grand Harbour

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 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.