Lodging Image

Winsor Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Winsor holiday rentals

Iron/ironing board, free WiFi, bed sheets

QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
7.4 out of 10, Good, (3 reviews)
"Very comfortable and clean place! It had many amazing restaurants and shops nearby"
United Kingdom
Shiona
The price is HK$1,188
HK$1,425 total
includes taxes & fees
3 Jul - 4 Jul
QE2 Loft Apartments
Iron/ironing board, free WiFi

Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.4 out of 10, Very good, (6 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is HK$497
HK$1,062 total
includes taxes & fees
5 Jul - 6 Jul
Settle Southampton
Exterior

The South Coast Snug

The South Coast Snug
2.0 star property
Fareham
6.0 out of 10, (3 reviews)
"Lovely appartment.very welcoming, clean and tidy, all equipment was their to use for a pleasant stay.very quiet.would highly reccomend"
United Kingdom
Ian
The price is HK$559
HK$671 total
includes taxes & fees
30 Jun - 1 Jul
The South Coast Snug
Interior entrance

room2 Southampton Hometel

room2 Southampton Hometel
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,243 reviews)
"Beautiful boutique hotel. Breakfast was delicious, room spacious, staff friendly and polite. Very shorth walk to cruise terminal. Would recommend this hotel."
Canada
Lyne
The price is HK$811
HK$974 total
includes taxes & fees
5 Jul - 6 Jul
room2 Southampton Hometel
1 bedroom, free WiFi, bed sheets

Experience Elegance at Fola Homestay

Experience Elegance at Fola Homestay
2.0 star property
Southampton
The price is HK$671
HK$991 total
includes taxes & fees
12 Jul - 13 Jul
Experience Elegance at Fola Homestay
Iron/ironing board, free WiFi

Settle Winchester

Settle Winchester
2.0 star property
Winchester
The price is HK$404
HK$1,043 total
includes taxes & fees
5 Jul - 6 Jul
Settle Winchester
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$1,584
HK$1,811 total
includes taxes & fees
1 Jul - 2 Jul
Farm Cottage on a Secluded 9-acre Equestrian Small Holding
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$1,677
HK$2,205 total
includes taxes & fees
30 Jun - 1 Jul
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Exterior

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$1,604
HK$2,184 total
includes taxes & fees
3 Jul - 4 Jul
A stroll to Ringwood, near to New Forest & South Coast Beaches. Private Parking
Living area

Charles Hope Salisbury Centre

Charles Hope Salisbury Centre
3.5 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 HK$1,174
HK$1,409 total
includes taxes & fees
30 Jun - 1 Jul
Charles Hope Salisbury Centre
Exterior

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$1,605
HK$1,605 total
includes taxes & fees
6 Jul - 7 Jul
1 bedroom accommodation in Burgate, near Fordingbridge
WiFi, bed sheets, wheelchair access

Cozy detached bungalow with sunny garden

Cozy detached bungalow with sunny garden
Southampton
The price is HK$1,646
HK$2,236 total
includes taxes & fees
3 Jul - 4 Jul
Cozy detached bungalow with sunny garden
1 bedroom, individually decorated, individually furnished, free WiFi

Poddington Cottage

Poddington Cottage
3.0 star property
Salisbury
The price is HK$4,118
HK$4,941 total
includes taxes & fees
2 Jul - 3 Jul
Poddington Cottage
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, (104 reviews)
"Beautiful cottage. Warm and comfortable with all amenities. Convenient for exploring. Lovely enclosed garden for our dog. Thoroughly enjoyedour 3 night stay and would book again. Thank you. "
United Kingdom
MARIAN C.
The price is HK$1,811
HK$2,070 total
includes taxes & fees
14 Jul - 15 Jul
Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.
Beach nearby

West Sea View No 5 , Yarmouth

West Sea View No 5 , Yarmouth
Yarmouth
The price is HK$3,695
HK$3,695 total
includes taxes & fees
18 Jul - 19 Jul
West Sea View No 5 , Yarmouth
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$1,576
HK$1,773 total
includes taxes & fees
1 Jul - 2 Jul
Luxury shepherd's hut
Property grounds

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, (23 reviews)
"Awesome place to stay- we absolutely loved it and will be back"
United Kingdom
Edward
The price is HK$1,472
HK$1,689 total
includes taxes & fees
5 Jul - 6 Jul
Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR
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, (8 reviews)
"Accommodation was beautifully clean and well equipped in a great location. "
United Kingdom
Julie P.
The price is HK$1,323
HK$1,499 total
includes taxes & fees
6 Jul - 7 Jul
Beautiful 2 bedroom full-furnished semi-detached house with parking
Exterior

The Old Cart Shed, Rockbourne

The Old Cart Shed, Rockbourne
Fordingbridge
The price is HK$6,793
HK$6,793 total
includes taxes & fees
2 Jul - 3 Jul
The Old Cart Shed, Rockbourne
Fireplace

Robins Nest, Titchfield Common

Robins Nest, Titchfield Common
Fareham
The price is HK$6,923
HK$6,923 total
includes taxes & fees
13 Jul - 14 Jul
Robins Nest, Titchfield Common
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winsor Hotel Reviews

Leonardo Royal Southampton Grand Harbour

Leonardo Royal Southampton Grand Harbour

10/10 Excellent
"We had a very pleasant stay—the room was spotless and the staff were helpful and friendly. Breakfast was also good. Would not hesitate to book again."
Elizabeth 1-night trip
Posted 1 hour ago
Leonardo Royal Southampton Grand Harbour

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
  • Use the map to find apartments and other holiday homes in the Winsor neighbourhood you prefer
  • 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 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?

Mudeford, Dorset. Spectacular Seafront Views. Perfect Family Getaway. Driveway.: This holiday home rental outside of Winsor is located on the beach, and has a balcony, a selection of games and a BBQ 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.