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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 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, (1,360 reviews)
"Great location and friendly staff!"
United States
Gary
The price is 2.339.325 ₫
2.807.190 ₫ total
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
8.2 out of 10, Very good, (13 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is 1.425.524 ₫
3.265.857 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Settle Southampton
A bedroom with a bed, a bedside table with a lamp, a window with curtains, a mirror, and a wooden door with a metal handle.

3. Horseshoe Cottage

Horseshoe Cottage
3.0 star property
Romsey
10.0 out of 10, Exceptional, (1 review)
"Well presented and well equipped home. All the essentials plus more. Very family friendly."
United Kingdom
Peter
The price is 19.741.045 ₫
23.689.254 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Horseshoe Cottage
A bedroom with a large bed, a sofa, a TV, and a window with blinds.

4. 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 5.287.780 ₫
6.345.336 ₫ total
includes taxes & fees
26 Oct - 27 Oct
QE2 Loft Apartments
A bedroom with a bed, a TV, and a window with curtains.

5. Bayview Apartments

Bayview Apartments
2.0 star property
Southampton City Centre
7.8 out of 10, Good, (7 reviews)
"The apartment was reasonably priced, conveniently located to our destination and perfectly adequate for our needs."
United States
Donald
The price is 8.064.037 ₫
9.676.983 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Bayview Apartments
A bedroom with a bed, a wooden bench, a staircase, and a wall-mounted light fixture.

6. Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.2 out of 10, Wonderful, (41 reviews)
"Very friendly host with modern suites"
United Kingdom
Samuel
The price is 3.864.743 ₫
4.637.691 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Pinnacle Suites
A sign for Hotel Peartree, a serviced apartment, with contact information and website.

7. 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 3.418.394 ₫
4.102.073 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Peartree Serviced Apartments
A living room with a dark blue sofa, a round wooden coffee table, a dining table with chairs, a large abstract painting, a round mirror, and a window with curtains.

8. Charles Hope Salisbury Centre

Charles Hope Salisbury Centre
4.0 star property
Salisbury
9.4 out of 10, Exceptional, (10 reviews)
"Clean modern room, well equipped and great locaton"
United Kingdom
Theodros
The price is 2.869.398 ₫
3.443.278 ₫ total
includes taxes & fees
16 Nov - 17 Nov
Charles Hope Salisbury Centre
A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a radiator.

9. Settle Winchester

Settle Winchester
2.0 star property
Winchester City Center
The price is 1.069.220 ₫
3.149.339 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Settle Winchester
A wooden cabin with a glass table and wicker chairs on a deck.

10. Foxes Earth

Foxes Earth
3.0 star property
Salisbury
The price is 13.013.814 ₫
15.616.577 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Foxes Earth
A beach with boats, a pier, and beach huts.

11. Isle 2-bed Retreat- Sleeps 4, Garden & Games Room

Isle 2-bed Retreat- Sleeps 4, Garden & Games Room
3.0 star property
Cowes
The price is 3.680.710 ₫
6.905.219 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Isle 2-bed Retreat- Sleeps 4, Garden & Games Room
Exterior

12. The South Coast Snug

The South Coast Snug
2.0 star property
Fareham
7.4 out of 10, Good, (6 reviews)
"Fantastic place great location everything close by"
United Kingdom
Nikki
The price is 1.866.966 ₫
2.240.359 ₫ total
includes taxes & fees
4 Nov - 5 Nov
The South Coast Snug
A brick house with a large front porch, a dining table set up outside, and a well-maintained lawn.

13. Bridge Farmhouse

Bridge Farmhouse
4.0 star property
Salisbury
9.2 out of 10, Wonderful, (19 reviews)
"Staying here felt like you walked into a story book; beautiful gardens, bridge over the creek with swans swimming up and down, sheep in the fields, views of Salisbury Cathedral, stylish decorated rooms. We greatly enjoyed our stay. "
Canada
Jennifer E
The price is 52.164.985 ₫
62.597.982 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Bridge Farmhouse
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.

14. 7 Wild Haven

7 Wild Haven
3.0 star property
Salisbury
7 Wild Haven
A modern kitchen with dark cabinets, a microwave, and a stove.

15. Stunning 2-bed Apt, Sleeps 6 in The New Forest

Stunning 2-bed Apt, Sleeps 6 in The New Forest
4.0 star property
Southampton
The price is 4.600.887 ₫
8.216.795 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Stunning 2-bed Apt, Sleeps 6 in The New Forest
A pier extending into calm waters with a clear sky above.

16. 2 Bedroom Apartment With Balcony, Double Bed & Single Bed in Living Room

2 Bedroom Apartment With Balcony, Double Bed & Single Bed in Living Room
2.0 star property
Boscombe
The price is 4.043.030 ₫
4.851.636 ₫ total
includes taxes & fees
7 Nov - 8 Nov
2 Bedroom Apartment With Balcony, Double Bed & Single Bed in Living Room
A traditional brick house with a garden in front, featuring a pathway and a metal fence.

17. The Cheese House

The Cheese House
3.0 star property
Salisbury
10.0 out of 10, Exceptional, (1 review)
"Loved this house. Beautiful spaces, lots of room, all modern updates with rustic farm feel. Gorgeous property."
United States
Bobby
The price is 46.557.231 ₫
55.868.677 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Cheese House
A red brick building with a white door, numbered 22, and a small garden area with potted plants.

18. 19 Quayside Walk

19 Quayside Walk
3.5 star property
Southampton
The price is 17.949.075 ₫
21.538.890 ₫ total
includes taxes & fees
31 Oct - 1 Nov
19 Quayside Walk
A compact hotel room with a bed, a washing machine, a sink, and a bench.

19. 1 Bedroom Flat Apartment With hot tub on the Balcony & City View, Sleeps 4ppl

1 Bedroom Flat Apartment With hot tub on the Balcony & City View, Sleeps 4ppl
2.0 star property
Boscombe
The price is 3.815.795 ₫
4.578.954 ₫ total
includes taxes & fees
28 Oct - 29 Oct
1 Bedroom Flat Apartment With hot tub on the Balcony & City View, Sleeps 4ppl
A modern kitchen with a built-in island, a sink, and a clock on the wall.

20. 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 2.879.939 ₫
4.665.688 ₫ total
includes taxes & fees
4 Nov - 5 Nov
4thedome
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 Hotel Southampton

Leonardo Hotel Southampton

10/10 Excellent
"Great great location. Don’t need to stay near the pier and pay their price. Great value at this hotel, clean , modern,well maintained and excellent location. Bar and restaurant on site so no need to venture out hunting for something. Many friends stay near pier for pre cruises but way more expensive while this hotel is only 10 minutes to pier was way more cost effective. Uber was only 8 pounds. Definitely recommend this hotel for all singles couples and family."
Crystal 1-night trip
Posted 9 hours ago
Leonardo Hotel Southampton

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.