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Winsor Holiday Rentals

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Check prices for these dates

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

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, (1,348 reviews)
"Great location and friendly staff!"
United States
Gary
The price is NZ$200
includes taxes & fees
25 Oct - 26 Oct
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 NZ$536
includes taxes & fees
18 Oct - 19 Oct
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 NZ$244
includes taxes & fees
8 Oct - 9 Oct
Settle Southampton
A paved driveway leading to a wooden gate, a bicycle with a bag, and a shed in a garden setting.

4. Beautiful New Forest Hideaway

Beautiful New Forest Hideaway
West Wellow
10.0 out of 10, Exceptional, (1 review)
"Lovely cottage!! Clean and had everything you could possibly need!! Our stay was so relaxing we didn’t want to leave and will be back soon !!"
United States
Alena M.
The price is NZ$412
includes taxes & fees
7 Oct - 8 Oct
Beautiful New Forest Hideaway
A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a radiator.

5. Settle Winchester

Settle Winchester
2.0 star property
Winchester City Center
The price is NZ$244
includes taxes & fees
25 Oct - 26 Oct
Settle Winchester
A hotel room with a bed, bedside table, and a desk with chairs. There is a window with a view of greenery outside.

6. New Forest National Park Studio @Forest Palms

New Forest National Park Studio @Forest Palms
Hyde
10.0 out of 10, Exceptional, (10 reviews)
"We loved it! It was very clean, comfy and welcoming. The garden had lovely flowers. We enjoyed the very nice pool as well. It was a little piece of paradise in a lovely area of England. We hope to come back again soon."
Germany
Dan R.
The price is NZ$373
includes taxes & fees
14 Oct - 15 Oct
New Forest National Park Studio @Forest Palms
A row of wooden cabins with attached porches, each with a small porch light.

7. Farm Cottage on a Secluded 9-acre Equestrian Small Holding

Farm Cottage on a Secluded 9-acre Equestrian Small Holding
Salisbury
10.0 out of 10, Exceptional, (17 reviews)
"Lovely accommadition all you could need for a get away, we only stayed 1 night wish it could have been more. Only issue main entrance is rather secluded.Hope to return for a longer stay, peaceful and secluded"
United States
Diana T.
The price is NZ$363
includes taxes & fees
11 Oct - 12 Oct
Farm Cottage on a Secluded 9-acre Equestrian Small Holding
A traditional thatched-roof cottage with a brick extension, a white door, and a small window.

8. 1 bedroom accommodation in Burgate, near Fordingbridge

1 bedroom accommodation in Burgate, near Fordingbridge
Burgate, near Fordingbridge
10.0 out of 10, Exceptional, (11 reviews)
"Perfect for a weekend away."
United States
Angela Horn
The price is NZ$304
includes taxes & fees
30 Oct - 31 Oct
1 bedroom accommodation in Burgate, near Fordingbridge
A calm lake with ducks and a swan, a boat docked on the left, and a building in the background.

9. Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton

Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton
Portswood
10.0 out of 10, Exceptional, (1 review)
"We had a great time, lovely neighborhood, location is easy access to needed items. Marvin is an excellent host. He responds right away with all questions. For a home that is 140 years old it is in excellent shape. Beautifully decorated. Everything we needed was there. Big plus to be on the water. Thank you Marvin!"
United States
Terri M.
The price is NZ$338
includes taxes & fees
12 Oct - 13 Oct
Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton
A modern kitchen with a central island, bar stools, hanging plants, and a variety of appliances.

10. Adorable 2-bedroom apartment in Southampton

Adorable 2-bedroom apartment in Southampton
Freemantle
9.0 out of 10, Wonderful, (4 reviews)
"Apartment was in great condition, no complaints!"
United Kingdom
Bethany M.
The price is NZ$426
includes taxes & fees
7 Oct - 8 Oct
Adorable 2-bedroom apartment in Southampton
A narrow stream with clear water, surrounded by lush greenery and wildflowers.

11. Roslyn

Roslyn
2.0 star property
Romsey
The price is NZ$1,221
includes taxes & fees
19 Oct - 20 Oct
Roslyn
A corner room with a large window overlooking a city street and buildings.

12. 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 NZ$316
includes taxes & fees
18 Oct - 19 Oct
Ocean Quay Luxury - Stylish 2 Bed - Has Parking
A bedroom with a large bed, a sofa, a TV, and a window with blinds.

13. 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 NZ$390
includes taxes & fees
8 Oct - 9 Oct
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.

14. 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 NZ$268
includes taxes & fees
7 Oct - 8 Oct
Charles Hope Salisbury Centre
A wooden cabin with an open door revealing a kitchen area, two wicker chairs, and a small wooden table.

15. Luxury shepherd's hut

Luxury shepherd's hut
Bransgore
9.8 out of 10, Exceptional, (43 reviews)
"We had the best stay in this beautiful shepherds hut. The location was perfect, the position of the shepherds hut allowed for guest privacy while also offering wonderful views and outdoor space. The accommodation was perfect with everything you could need. Would highly recommend. "
United Kingdom
Hayley M.
The price is NZ$401
includes taxes & fees
19 Oct - 20 Oct
Luxury shepherd's hut
A coastal beach with a rocky cliff and a clear view of the sea.

16. Unique detached holiday cottage, Hampshire

Unique detached holiday cottage, Hampshire
Sopley
9.8 out of 10, Exceptional, (84 reviews)
"Great place for a short stay"
United Kingdom
Keiron D.
The price is NZ$324
includes taxes & fees
7 Oct - 8 Oct
Unique detached holiday cottage, Hampshire
A sign for Hotel Peartree, a serviced apartment, with contact information and website.

17. 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 NZ$286
includes taxes & fees
1 Nov - 2 Nov
Peartree Serviced Apartments
A mobile home with a white exterior, a deck with white railings, and a black roof vent labeled "ABI 50A".

18. New Forest & coastal retreat

New Forest & coastal retreat
New Milton
10.0 out of 10, Exceptional, (4 reviews)
"The caravan was spotlessly clean and we had everything we needed for our stay. The shower leaked a bit and was difficult to control the temperature but no biggy really. We paid extra for passes to the site facilities. We used the clubhouse for food and drinks, pool etc. well worth the little extra. Alison was a great host with quick and easy communication. Would recommend "
United States
Al D.
The price is NZ$470
includes taxes & fees
27 Oct - 28 Oct
New Forest & coastal retreat
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)
"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 NZ$342
includes taxes & fees
2 Nov - 3 Nov
4thedome
Property grounds

20. Moonwood House - Welcome to country living at its very finest.

Moonwood House - Welcome to country living at its very finest.
Beaulieu
9.8 out of 10, Exceptional, (11 reviews)
"Superb accommodation pristine throughout, ideal location for local pubs walks and restaurants, Would recommend for a family get together, the children loved it too"
United States
Anonymous traveller
The price is NZ$5,893
includes taxes & fees
7 Oct - 8 Oct
Moonwood House - Welcome to country living at its very finest.
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 1 hour ago
Harbour Hotel Southampton

Find out more about Winsor

Everything you need to know about Winsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winsor holiday rentals we have selected for you start as low as NZ$200 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winsor rentals

At Expedia, we put the best Winsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 are some of the best holiday rentals that Winsor has to offer?

Unique waterside home in stunning location.: This holiday home rental outside of Winsor is located on the waterfront, and has a balcony, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.