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Winsor Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winsor holiday rentals

A kitchen with grey cabinets, a microwave, an oven, a sink, and a wooden countertop.

1. 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 HK$1,279
HK$2,345 total
includes taxes & fees
11 Oct - 12 Oct
Stunning 2-bed Apt, Sleeps 6 in The New Forest
A modern interior with a red sofa, black chairs, and a patterned floor.

2. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,342 reviews)
"Great location and friendly staff!"
United States
Gary
The price is HK$733
HK$880 total
includes taxes & fees
4 Oct - 5 Oct
Second Nature Southampton
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 HK$499
HK$1,066 total
includes taxes & fees
5 Oct - 6 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 HK$1,296
HK$1,815 total
includes taxes & fees
5 Oct - 6 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 HK$316
HK$940 total
includes taxes & fees
4 Oct - 5 Oct
Settle Winchester
A row of wooden cabins with attached porches, each with a small porch light.

6. 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 HK$1,422
HK$1,630 total
includes taxes & fees
8 Oct - 9 Oct
Farm Cottage on a Secluded 9-acre Equestrian Small Holding
A dining table set with plates, cutlery, and a glass vase with yellow flowers.

7. 3 Bedrooms house ideal for long Stays!

3 Bedrooms house ideal for long Stays!
Southampton
10.0 out of 10, Exceptional, (5 reviews)
"Great location, lovely clean property can recommend."
United Kingdom
Michael R.
3 Bedrooms house ideal for long Stays!
A calm lake with ducks and a swan, a boat docked on the left, and a building in the background.

8. 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 HK$1,216
HK$1,486 total
includes taxes & fees
30 Sept - 1 Oct
Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton
An outdoor patio with wooden furniture, a table set for dining, and a pergola with climbing plants.

9. New Forest National Park Studio @Forest Palms

New Forest National Park Studio @Forest Palms
Hyde
10.0 out of 10, Exceptional, (10 reviews)
"We had a fabulous time at New Forest Palms. Super clean and modern apartment with all you need nearby! Pubs, food, wild horses. 😊"
United Kingdom
Hazel D.
The price is HK$1,227
HK$1,643 total
includes taxes & fees
1 Oct - 2 Oct
New Forest National Park Studio @Forest Palms
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 HK$1,469
HK$1,843 total
includes taxes & fees
3 Oct - 4 Oct
Adorable 2-bedroom apartment in Southampton
A compact kitchen with wooden cabinets, a built-in washing machine, a gas stove, and a tiled backsplash.

11. 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 HK$1,217
HK$1,461 total
includes taxes & fees
14 Oct - 15 Oct
Ocean Quay Luxury - Stylish 2 Bed - Has Parking
A traditional thatched-roof cottage with a brick extension, a white door, and a small window.

12. 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 HK$1,338
HK$1,338 total
includes taxes & fees
30 Oct - 31 Oct
1 bedroom accommodation in Burgate, near Fordingbridge
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
5.4 out of 10, (13 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 HK$1,431
HK$1,717 total
includes taxes & fees
1 Oct - 2 Oct
QE2 Loft Apartments
A wooden cabin with an open door revealing a kitchen area, two wicker chairs, and a small wooden table.

14. 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 HK$1,582
HK$1,748 total
includes taxes & fees
30 Sept - 1 Oct
Luxury shepherd's hut
A coastal beach with a rocky cliff and a clear view of the sea.

15. 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 HK$898
HK$1,439 total
includes taxes & fees
7 Oct - 8 Oct
Unique detached holiday cottage, Hampshire
A mobile home with a white exterior, a deck with white railings, and a black roof vent labeled "ABI 50A".

16. 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 HK$1,496
HK$1,870 total
includes taxes & fees
30 Sept - 1 Oct
New Forest & coastal retreat
A narrow stream with clear water, surrounded by lush greenery and wildflowers.

17. Roslyn

Roslyn
2.0 star property
Romsey
The price is HK$4,478
HK$5,373 total
includes taxes & fees
8 Oct - 9 Oct
Roslyn
A row of seaside cottages with large windows and a stone roof.

18. Beachfront Beach Hut with Stunning coastal views

Beachfront Beach Hut with Stunning coastal views
Bournemouth
10.0 out of 10, Exceptional, (5 reviews)
"We were very impressed with how well the hut was set up & the efficiency of the storage. It was a fabulous location with all of the information that we needed to stay there. Highly recommended & would love to return again!"
United Kingdom
Hannah N.
The price is HK$832
HK$1,248 total
includes taxes & fees
13 Oct - 14 Oct
Beachfront Beach Hut with Stunning coastal views
A two-story brick house with white doors and windows, a gravel driveway, and a black metal fence.

19. A stroll to Ringwood, near to New Forest & South Coast Beaches. Private Parking

A stroll to Ringwood, near to New Forest & South Coast Beaches. Private Parking
Ringwood
10.0 out of 10, Exceptional, (13 reviews)
"very modern and clean accommodation local to shops and bars"
United Kingdom
Donna E.
The price is HK$1,591
HK$2,069 total
includes taxes & fees
22 Oct - 23 Oct
A stroll to Ringwood, near to New Forest & South Coast Beaches. Private Parking
A hammock between trees overlooking a beach with boats and a fence.

20. Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR

Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR
Cowes
10.0 out of 10, Exceptional, (26 reviews)
"Awesome place to stay- we absolutely loved it and will be back"
United Kingdom
Edward
The price is HK$1,263
HK$1,450 total
includes taxes & fees
5 Oct - 6 Oct
Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR
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

ibis Southampton Centre

ibis Southampton Centre

10/10 Excellent
"Ibis was close to the cruise port and that was important for us. The hotel was comfortable and clean."
Susan 2-night trip
Posted 3 hours ago
ibis Southampton Centre

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:

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Look no further and take a look at our great range of rental properties in Winsor!

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.