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Winsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winsor vacation 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, (1,348 reviews)
"Great location and friendly staff!"
United States
Gary
The price is P5,842
P7,011 total
includes taxes & fees
Oct 25 - Oct 26
Second Nature Southampton
A kitchen with grey cabinets, a microwave, an oven, a sink, and a wooden countertop.

2. 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 P10,291
P18,809 total
includes taxes & fees
Oct 11 - Oct 12
Stunning 2-bed Apt, Sleeps 6 in The New Forest
A bedroom with a large bed, a wooden ceiling, and a view of a brick building outside.

3. 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 P4,348
P8,945 total
includes taxes & fees
Oct 11 - Oct 12
Settle Southampton
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 P3,541
P8,721 total
includes taxes & fees
Oct 25 - Oct 26
Settle Winchester
A narrow stream with clear water, surrounded by lush greenery and wildflowers.

5. Roslyn

Roslyn
2.0 star property
Romsey
The price is P35,693
P42,832 total
includes taxes & fees
Oct 19 - Oct 20
Roslyn
A corner room with a large window overlooking a city street and buildings.

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

Ocean Quay Luxury - Stylish 2 Bed - Has Parking
3.0 star property
Southampton City Centre
The price is P9,924
P11,908 total
includes taxes & fees
Oct 11 - Oct 12
Ocean Quay Luxury - Stylish 2 Bed - Has Parking
A bedroom with a large bed, a sofa, a TV, and a window with blinds.

7. QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
5.6 out of 10, (14 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 P11,405
P13,686 total
includes taxes & fees
Oct 8 - Oct 9
QE2 Loft 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 P7,827
P9,392 total
includes taxes & fees
Oct 7 - Oct 8
Charles Hope Salisbury Centre
A sign for Hotel Peartree, a serviced apartment, with contact information and website.

9. 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 P9,280
P11,136 total
includes taxes & fees
Nov 1 - Nov 2
Peartree Serviced Apartments
A modern kitchen with a built-in island, a sink, and a clock on the wall.

10. 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 P7,592
P12,010 total
includes taxes & fees
Nov 2 - Nov 3
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

Harbour Hotel Southampton

Harbour Hotel Southampton

10/10 Excellent
"Very near cruise terminal. Staff especially helpful."
Janet 2-night trip
Posted 3 hours ago
Harbour Hotel Southampton

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
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  • 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 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.