Winsor Holiday Rentals

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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Winsor holiday rentals

Interior entrance

room2 Southampton Hometel

room2 Southampton Hometel
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,216 reviews)
"Friendly staff - great breakfast food options "
United Kingdom
Christian
The price is HK$855
HK$1,026 total
includes taxes & fees
1 Jun - 2 Jun
room2 Southampton Hometel
TV

The Cabin by NewFo.rest

The Cabin by NewFo.rest
Brockenhurst
10.0 out of 10, Exceptional, (3 reviews)
"just the amount of space i needed in the place i needed."
United States
John
The price is HK$1,367
HK$2,202 total
includes taxes & fees
20 May - 21 May
The Cabin by NewFo.rest
Exterior

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, (13 reviews)
"Lovely 1 night stay in beautiful location. Louise very welcoming and property was perfect and very clean."
United Kingdom
Emily S.
The price is HK$2,191
HK$2,505 total
includes taxes & fees
17 Jun - 18 Jun
Farm Cottage on a Secluded 9-acre Equestrian Small Holding
Fridge, microwave, oven, dishwasher

Beautiful 2 bedroom full-furnished semi-detached house with parking

Beautiful 2 bedroom full-furnished semi-detached house with parking
Dibden Purlieu
9.6 out of 10, Exceptional, (7 reviews)
"Accommodation was beautifully clean and well equipped in a great location. "
United Kingdom
Julie P.
The price is HK$1,315
HK$1,482 total
includes taxes & fees
21 May - 22 May
Beautiful 2 bedroom full-furnished semi-detached house with parking
Iron/ironing board, free WiFi

Settle Winchester

Settle Winchester
2.0 star property
Winchester
The price is HK$385
HK$1,495 total
includes taxes & fees
7 Jun - 8 Jun
Settle Winchester
Exterior

1 bedroom accommodation in Burgate, near Fordingbridge

1 bedroom accommodation in Burgate, near Fordingbridge
Burgate, near Fordingbridge
9.0 out of 10, Wonderful, (20 reviews)
"Lovely place to stay - comfortable and well equipped. Ideal location."
United Kingdom
Ruth P.
The price is HK$2,468
HK$2,468 total
includes taxes & fees
20 May - 21 May
1 bedroom accommodation in Burgate, near Fordingbridge
Outdoor dining

Cape 12,

Cape 12,
2.0 star property
Yarmouth
The price is HK$3,113
HK$3,736 total
includes taxes & fees
22 May - 23 May
Cape 12,
Iron/ironing board, free WiFi

Settle Southampton

Settle Southampton
2.0 star property
Freemantle
10.0 out of 10, Exceptional, (2 reviews)
"I had trouble getting in so I messaged and received a response very quickly Good location Clean room"
United Kingdom
elysha
The price is HK$493
HK$1,061 total
includes taxes & fees
1 Jun - 2 Jun
Settle Southampton
Living area

Charles Hope Salisbury Centre

Charles Hope Salisbury Centre
3.5 star property
Salisbury
9.8 out of 10, Exceptional, (6 reviews)
"Great location and well appointed apartment"
Australia
Greg
The price is HK$1,115
HK$1,338 total
includes taxes & fees
4 Jun - 5 Jun
Charles Hope Salisbury Centre
Terrace/patio

Cosy A-Frame cabin nestled in the chalk steams of Hampshire

Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Winchester
9.0 out of 10, Wonderful, (4 reviews)
"Lovely cabin and outside kitchen plus garden. It's my second stay and I enjoyed my stay. Love the garden kitchen,. It's very pretty and relaxing ."
United Kingdom
Nicola H.
The price is HK$1,691
HK$2,233 total
includes taxes & fees
21 May - 22 May
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Spa

Beautiful 4 berth boat on the Isle of Wight for the ultimate relaxation

Beautiful 4 berth boat on the Isle of Wight for the ultimate relaxation
Binfield
10.0 out of 10, Exceptional, (1 review)
"Best stay! Very new experience of staying in a boat. Amazing location for public services as well. "
United Kingdom
srini k.
The price is HK$1,774
HK$2,014 total
includes taxes & fees
20 May - 21 May
Beautiful 4 berth boat on the Isle of Wight for the ultimate relaxation
Miscellaneous

Beddoe Apartments

Beddoe Apartments
3.0 star property
Eastleigh
8.2 out of 10, Very good, (19 reviews)
"Ideal for couple of nights stay. Easy parking was a bonus. "
United Kingdom
Alan
The price is HK$1,261
HK$1,983 total
includes taxes & fees
25 May - 26 May
Beddoe Apartments
Terrace/patio

Luxury shepherd's hut

Luxury shepherd's hut
Bransgore
9.8 out of 10, Exceptional, (43 reviews)
"The hut was in great condition, with luxurious amenities and amazing views of the countryside. It made for a very peaceful and welcoming stay!"
United States
Paul A.
The price is HK$1,589
HK$1,756 total
includes taxes & fees
20 May - 21 May
Luxury shepherd's hut
Exterior

Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.

Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.
Stockbridge
9.6 out of 10, Exceptional, (102 reviews)
"Pretty and comfortable cottage - was lovely and warm. Lovely touch to have a Christmas tree and lights. We all thoroughly enjoyed our stay. "
United Kingdom
Karen D.
The price is HK$1,826
HK$2,087 total
includes taxes & fees
7 Jun - 8 Jun
Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.
Terrace/patio

A Hidden Gem With Private Hot Tub and Garden

A Hidden Gem With Private Hot Tub and Garden
Bournemouth
8.6 out of 10, Excellent, (9 reviews)
"Property was as described. Had a pleasant stay"
United Kingdom
Michelle A.
The price is HK$1,056
HK$1,547 total
includes taxes & fees
20 May - 21 May
A Hidden Gem With Private Hot Tub and Garden
Property grounds

Cosy Cottage by the Sea (1x BIG Master Double Bedroom)

Cosy Cottage by the Sea (1x BIG Master Double Bedroom)
Cowes
10.0 out of 10, Exceptional, (20 reviews)
"This is a lovely old cottage with lots of character. Two minutes walk from the esplanade, and an easy walk into Cowes. Dan was an outstanding host who looked after us very well 😁 Would highly recommend if visiting the Isle of Wight. Spacious bedroom with private facilities, even a log fire for those chilly evenings."
Australia
Barrie
The price is HK$977
HK$1,144 total
includes taxes & fees
25 May - 26 May
Cosy Cottage by the Sea (1x BIG Master Double Bedroom)
Outdoor dining

The Happy Hut

The Happy Hut
2.0 star property
Christchurch
The price is HK$3,096
HK$3,715 total
includes taxes & fees
6 Jun - 7 Jun
The Happy Hut
Marina

Daisy Haven in Southampton

Daisy Haven in Southampton
3.5 star property
Bassett Green
The price is HK$1,667
HK$2,000 total
includes taxes & fees
6 Jun - 7 Jun
Daisy Haven in Southampton
Premium bedding, Select Comfort beds, desk, laptop workspace

Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.8 out of 10, Exceptional, (27 reviews)
"The room was great!"
United Kingdom
Ash
The price is HK$1,209
HK$1,451 total
includes taxes & fees
24 May - 25 May
Pinnacle Suites
Terrace/patio

Port Side , Yarmouth

Port Side , Yarmouth
Yarmouth
The price is HK$3,331
HK$3,331 total
includes taxes & fees
21 May - 22 May
Port Side , Yarmouth
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

Village Hotel Bournemouth

Village Hotel Bournemouth

10/10 Excellent
"Fantastic place to stay. Lovely room and restaurant"
Sergio 1-night trip
Posted 2 hours ago
Village Hotel Bournemouth

Find out more about Winsor

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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.