A forested area with a dirt path, tall trees, and dense underbrush.

Search Holiday Homes in Winsor

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Winsor holiday homes

Interior

1. 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 £175
includes taxes & fees
6 Oct - 7 Oct
Beautiful New Forest Hideaway
Desk, iron/ironing board, WiFi, bed sheets

2. Cosy 4 bedroom Luxe House, with private parking, Great for Groups

Cosy 4 bedroom Luxe House, with private parking, Great for Groups
Bassett
The price is £443
includes taxes & fees
11 Oct - 12 Oct
Cosy 4 bedroom Luxe House, with private parking, Great for Groups
4 bedrooms, free WiFi, bed sheets

3. Eastleigh Luxury Retreat With 4 Bedrooms With Parking Near Airport

Eastleigh Luxury Retreat With 4 Bedrooms With Parking Near Airport
3.0 star property
Eastleigh
The price is £178
includes taxes & fees
4 Oct - 5 Oct
Eastleigh Luxury Retreat With 4 Bedrooms With Parking Near Airport
Property grounds

4. 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 £149
includes taxes & fees
29 Sept - 30 Sept
Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton
Dining

5. 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.
The price is £204
includes taxes & fees
27 Sept - 28 Sept
3 Bedrooms house ideal for long Stays!
Exterior

6. Historic studio annexe for two with New Forest on your doorstep

Historic studio annexe for two with New Forest on your doorstep
Burgate
The price is £140
includes taxes & fees
28 Sept - 29 Sept
Historic studio annexe for two with New Forest on your doorstep
2 bedrooms, free WiFi, bed sheets

7. Cozy detached bungalow with sunny garden

Cozy detached bungalow with sunny garden
Southampton
The price is £201
includes taxes & fees
22 Sept - 23 Sept
Cozy detached bungalow with sunny garden
Terrace/patio

8. 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 £177
includes taxes & fees
22 Sept - 23 Sept
Luxury shepherd's hut
Beach

9. 4-bedroom house in prime location

4-bedroom house in prime location
Hampshire
10.0 out of 10, Exceptional, (2 reviews)
"Had a lovely weekend. Lovely quiet place to stay. X"
United Kingdom
Laura B.
The price is £460
includes taxes & fees
18 Oct - 19 Oct
4-bedroom house in prime location
Smart TV, books, stereo

10. Peaceful barn stay near Lymington with private garden

Peaceful barn stay near Lymington with private garden
Lymington
8.0 out of 10, Very good, (1 review)
"Great host and property had a lovely stay"
United Kingdom
Carly
The price is £217
includes taxes & fees
7 Oct - 8 Oct
Peaceful barn stay near Lymington with private garden
Interior

11. Two rooms in a very quiet and clean environment. Central to getting services

Two rooms in a very quiet and clean environment. Central to getting services
Southampton
6.0 out of 10, (1 review)
"You get what you pay for"
Canada
Tom
The price is £97
includes taxes & fees
4 Oct - 5 Oct
Two rooms in a very quiet and clean environment. Central to getting services
Exterior

12. The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.

The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.
Clarendon
The price is £255
includes taxes & fees
21 Sept - 22 Sept
The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.
Interior

13. 3BR Luxury Chic Spacious House w/Parking -Sleeps 7

3BR Luxury Chic Spacious House w/Parking -Sleeps 7
Bevois Valley
The price is £450
includes taxes & fees
18 Oct - 19 Oct
3BR Luxury Chic Spacious House w/Parking -Sleeps 7
Exterior

14. Quirky Railway Carriages

Quirky Railway Carriages
Hinton
9.6 out of 10, Exceptional, (5 reviews)
"We booked a last minute short break with our dog Bear. The Railway Carriages was a lovely quirky place with a fabulous big fully enclosed garden which Bear loved. It was lovely and clean with comfy beds. Great location for New Forest and local beaches. We will definitely come again."
United States
Sally
The price is £265
includes taxes & fees
24 Sept - 25 Sept
Quirky Railway Carriages
TV, video games

15. The Summer House — Unique Hilltop Retreat for up to 4 ppl.

The Summer House — Unique Hilltop Retreat for up to 4 ppl.
Salisbury
The price is £269
includes taxes & fees
21 Sept - 22 Sept
The Summer House — Unique Hilltop Retreat for up to 4 ppl.
Fridge, microwave, oven, stovetop

16. 4BR Lymington Home near New Forest & Coast

4BR Lymington Home near New Forest & Coast
Hampshire
The price is £416
includes taxes & fees
21 Sept - 22 Sept
4BR Lymington Home near New Forest & Coast
Property grounds

17. Cozy & Self Contained The Garden Annex 306

Cozy & Self Contained The Garden Annex 306
Salisbury
10.0 out of 10, Exceptional, (3 reviews)
"This place was lovely! Incredibly quiet for being in the city."
United States
Dala B.
The price is £99
includes taxes & fees
29 Sept - 30 Sept
Cozy & Self Contained The Garden Annex 306
Beach

18. Coastal 2-Bed Apartment Sleeps 5 · 5-Min Walk to Beach · Milford-on-Sea

Coastal 2-Bed Apartment Sleeps 5 · 5-Min Walk to Beach · Milford-on-Sea
Milford on Sea
The price is £223
includes taxes & fees
23 Sept - 24 Sept
Coastal 2-Bed Apartment Sleeps 5 · 5-Min Walk to Beach · Milford-on-Sea
Exterior detail

19. 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 £130
includes taxes & fees
4 Oct - 5 Oct
Beachfront Beach Hut with Stunning coastal views
Desk, iron/ironing board, WiFi, bed sheets

20. Lovely 5 bedroom holiday home with a games room

Lovely 5 bedroom holiday home with a games room
Christchurch
The price is £377
includes taxes & fees
21 Sept - 22 Sept
Lovely 5 bedroom holiday home with a games room
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

Moxy Southampton

Moxy Southampton

10/10 Excellent
"Good location"
Patrick 1-night trip
Posted 9 hours ago
Moxy Southampton

Find out more about Winsor

Winsor Holiday Homes information

Number of reviews
Accommodation
580 Holiday Homes
Lowest Price
£1,094
Highest Price
£1,094

Explore a world of travel with Expedia