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Winsor Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

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, (1,311 reviews)
"Great place to stay on the way to our cruise…would definitely recommend!!"
Canada
Shelly
The price is S$176
includes taxes & fees
31 Aug - 1 Sept
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
8.8 out of 10, Excellent, (8 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is S$156
includes taxes & fees
31 Aug - 1 Sept
Settle Southampton
A bedroom with a large bed, a sofa, a TV, and a window with blinds.

3. QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
6.4 out of 10, (8 reviews)
"No Air conditioning! Bar under with loud party all night long. Windows open for air. You book this room only if you want to party. Otherwise you will be kept up all night long. 90 degrees outside and hotter inside do to restaurant ovens directly under room. It was the worst experience. Jet lag turned into nightmare 😫"
United States
BRIAN
The price is S$272
includes taxes & fees
3 Sept - 4 Sept
QE2 Loft Apartments

4. Property

Property
3.0 star property
Bevois Valley
The price is S$264
includes taxes & fees
10 Sept - 11 Sept
Property
A wooden cabin with a glass table and wicker chairs on a deck.

5. Foxes Earth

Foxes Earth
3.0 star property
Salisbury
The price is S$779
includes taxes & fees
4 Sept - 5 Sept
Foxes Earth
A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a radiator.

6. Settle Winchester

Settle Winchester
2.0 star property
Winchester
The price is S$174
includes taxes & fees
6 Sept - 7 Sept
Settle Winchester
A bedroom with a bed, a TV, and a window with curtains.

7. Bayview Apartments

Bayview Apartments
2.0 star property
Southampton City Centre
8.0 out of 10, Very good, (5 reviews)
"The apartment was reasonably priced, conveniently located to our destination and perfectly adequate for our needs."
United States
Donald
The price is S$276
includes taxes & fees
2 Sept - 3 Sept
Bayview Apartments
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, (325 reviews)
"Clean and quiet. Had what we needed to cook. Walkable distance from grocery store, pharmacy. Next to train station. Would go back!"
Canada
Karine
The price is S$280
includes taxes & fees
27 Sept - 28 Sept
Peartree Serviced Apartments
A bedroom with a bed, a wooden bench, a staircase, and a wall-mounted light fixture.

9. Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.2 out of 10, Wonderful, (40 reviews)
"Very friendly host with modern suites"
United Kingdom
Samuel
The price is S$274
includes taxes & fees
11 Sept - 12 Sept
Pinnacle Suites
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.

10. Charles Hope Salisbury Centre

Charles Hope Salisbury Centre
4.0 star property
Salisbury
9.4 out of 10, Exceptional, (9 reviews)
"Clean modern room, well equipped and great locaton"
United Kingdom
Theodros
The price is S$353
includes taxes & fees
1 Sept - 2 Sept
Charles Hope Salisbury Centre
A living room with a sofa, a coffee table, and a TV. There is a dining area with a table and chairs in the background.

11. Salisbury Residences by Charles Hope

Salisbury Residences by Charles Hope
4.0 star property
Salisbury
The price is S$700
includes taxes & fees
4 Sept - 5 Sept
Salisbury Residences by Charles Hope

12. 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 S$219
includes taxes & fees
10 Sept - 11 Sept
1 Bedroom Flat Apartment With hot tub on the Balcony & City View, Sleeps 4ppl
A modern house with a patio area featuring a sofa, chairs, and a dining table.

13. Pamper House Holiday Home And Annex

Pamper House Holiday Home And Annex
3.0 star property
Ferndown
The price is S$1,747
includes taxes & fees
28 Sept - 29 Sept
Pamper House Holiday Home And Annex

14. 1 Bed Flat - Sleeps 2 - Parking - Wifi

1 Bed Flat - Sleeps 2 - Parking - Wifi
3.0 star property
The Polygon
The price is S$797
includes taxes & fees
1 Sept - 2 Sept
1 Bed Flat - Sleeps 2 - Parking - Wifi
A red brick building with a white door, numbered 22, and a small garden area with potted plants.

15. 19 Quayside Walk

19 Quayside Walk
3.5 star property
Southampton
The price is S$1,126
includes taxes & fees
19 Sept - 20 Sept
19 Quayside Walk
A brick house with a large front porch, a dining table set up outside, and a well-maintained lawn.

16. 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 S$3,266
includes taxes & fees
31 Aug - 1 Sept
Bridge Farmhouse
A beach with boats, a pier, and beach huts.

17. 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 S$334
includes taxes & fees
16 Sept - 17 Sept
Isle 2-bed Retreat- Sleeps 4, Garden & Games Room
A bedroom with a wooden door, a bed with a beige and white striped bedspread, a fluffy beige throw blanket, and a pink pillow. There are framed pictures on the wall and a window with curtains.

18. The Bike Shed

The Bike Shed
3.0 star property
Romsey
The price is S$707
includes taxes & fees
12 Sept - 13 Sept
The Bike Shed
A modern kitchen with a built-in island, a sink, and a clock on the wall.

19. 4thedome

4thedome
3.5 star property
New Milton
9.4 out of 10, Exceptional, (13 reviews)
"Excellent, will definitely be back, bedding and towels provided, great location, excellent communication "
United Kingdom
Claire
The price is S$268
includes taxes & fees
31 Aug - 1 Sept
4thedome
A narrow stream with clear water, surrounded by lush greenery and wildflowers.

20. Roslyn

Roslyn
2.0 star property
Romsey
The price is S$892
includes taxes & fees
27 Sept - 28 Sept
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
"Stay was great. Very close to port for cruise. Only one issue, but it was not with the hotel. Concierge scheduled us a taxi for travel to port, literally 6 blocks away. Taxi charged us $20. It was 2 people & 2 medium suitcases, and 2 backpacks that we kept with us. Definitely would recommend using Uber."
Karen 2-night trip
Posted 8 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.