Winsor Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Winsor vacation rentals

Free WiFi

Pebbles Guest House - Flat 5

Pebbles Guest House - Flat 5
2.0 star property
Freemantle
The price is P2,674
P3,208 total
includes taxes & fees
Feb 16 - Feb 17
Pebbles Guest House - Flat 5
Interior entrance

room2 Southampton Hometel

room2 Southampton Hometel
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,197 reviews)
"Great location and vibe"
United Kingdom
Paul
The price is P4,955
P5,945 total
includes taxes & fees
Feb 22 - Feb 23
room2 Southampton Hometel
1 bedroom, in-room safe, desk, iron/ironing board

Southampton Serviced Apartment

Southampton Serviced Apartment
4.0 star property
Bassett
8.4 out of 10, Very Good, (179 reviews)
"Ideal, close to Univeristy. "
United Kingdom
Sheena
The price is P9,572
P11,487 total
includes taxes & fees
Feb 18 - Feb 19
Southampton Serviced Apartment
Restaurant

The Cliff House Hotel

The Cliff House Hotel
4.0 star property
New Milton
9.4 out of 10, Exceptional, (409 reviews)
"Room and staff excellent enjoyed our stay food good"
United Kingdom
Keith
The price is P8,516
P10,219 total
includes taxes & fees
Feb 16 - Feb 17
The Cliff House Hotel
Free WiFi

Pebbles Guest House - Flat 7

Pebbles Guest House - Flat 7
2.0 star property
Freemantle
The price is P3,565
P4,278 total
includes taxes & fees
Feb 16 - Feb 17
Pebbles Guest House - Flat 7
Premium bedding, Select Comfort beds, desk, laptop workspace

Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.8 out of 10, Exceptional, (26 reviews)
"Great place to stay. Facilities are very nice and clean. Zoe is a very helpful and kind host. "
Denmark
Sebastian
The price is P8,534
P10,241 total
includes taxes & fees
Feb 16 - Feb 17
Pinnacle Suites
Interior

6 Yarmouth Cottages

6 Yarmouth Cottages
3.0 star property
Freshwater
8.0 out of 10, Very Good, (4 reviews)
"A very pleasant place to stay in a lovely location on the western side of the island. It has lovely views over fields. The cottage was clean and well equipped. The bed was comfortable and the bathrooms and shower were of good quality. The owner was both friendly and helpful. Thank you :-)"
United Kingdom
Adam
The price is P23,633
P28,360 total
includes taxes & fees
Feb 20 - Feb 21
6 Yarmouth Cottages
Front of property

Peartree Serviced Apartments

Peartree Serviced Apartments
3.5 star property
Salisbury
9.6 out of 10, Exceptional, (308 reviews)
"Enjoyable stay, handy to Salisbury landmarks."
Australia
Heather
The price is P7,711
P9,254 total
includes taxes & fees
Feb 23 - Feb 24
Peartree Serviced Apartments
Private kitchen

Coventry Road Studio Flat

Coventry Road Studio Flat
2.0 star property
The Polygon
The price is P3,565
P4,278 total
includes taxes & fees
Feb 27 - Feb 28
Coventry Road Studio Flat
Property grounds

Crown Quarter Penthouse

Crown Quarter Penthouse
2.0 star property
Southampton City Centre
Crown Quarter Penthouse
2 bedrooms

Peaceful Retreat in Southampton's Countryside

Peaceful Retreat in Southampton's Countryside
2.0 star property
Southampton
The price is P13,560
P19,855 total
includes taxes & fees
Feb 16 - Feb 17
Peaceful Retreat in Southampton's Countryside
Free WiFi

Pebbles Guest House - Flat 6

Pebbles Guest House - Flat 6
2.0 star property
Freemantle
The price is P2,674
P3,208 total
includes taxes & fees
Feb 16 - Feb 17
Pebbles Guest House - Flat 6
2 bedrooms, iron/ironing board, free WiFi, bed sheets

2 Bed Flat - Sleeps 4 - Parking - Wifi

2 Bed Flat - Sleeps 4 - Parking - Wifi
3.0 star property
The Polygon
10.0 out of 10, Exceptional, (1 review)
"Great apartment, super friendly host!"
United Kingdom
Amy
The price is P19,153
P22,983 total
includes taxes & fees
Feb 16 - Feb 17
2 Bed Flat - Sleeps 4 - Parking - Wifi
Interior

4thedome

4thedome
3.5 star property
New Milton
9.4 out of 10, Exceptional, (12 reviews)
"Had a lovely stay in this apartment . It was excellent. Very very clean and comfortable, with everything you could need and a lot of little extras. Just a couple of steps over to the clifftop in Barton on sea. Would definitely stay again."
United Kingdom
Stephen
The price is P6,601
P10,695 total
includes taxes & fees
Feb 26 - Feb 27
4thedome
Exterior

Pamper House Holiday Home And Annex

Pamper House Holiday Home And Annex
3.0 star property
Ferndown
Pamper House Holiday Home And Annex
Living room

5 Yarmouth Cottages

5 Yarmouth Cottages
3.5 star property
Freshwater
9.4 out of 10, Exceptional, (3 reviews)
"Convenient and spotlessly clean small cottage is a great base for exploring the IoW. Only slight downside is that the proximity to other guests means sitting outside can be a little bit of an exercise in hearing other people’s conversation! This small point aside, can recommend for a short stay. "
United Kingdom
Clive
The price is P23,633
P28,360 total
includes taxes & fees
Feb 20 - Feb 21
5 Yarmouth Cottages
Exterior

The South Coast Snug

The South Coast Snug
2.0 star property
Fareham
The price is P5,333
P6,400 total
includes taxes & fees
Mar 5 - Mar 6
The South Coast Snug
Exterior

The Cheese House

The Cheese House
3.0 star property
Salisbury
10.0 out of 10, Exceptional, (1 review)
"Loved this house. Beautiful spaces, lots of room, all modern updates with rustic farm feel. Gorgeous property."
United States
Bobby
The price is P104,346
P125,215 total
includes taxes & fees
Feb 20 - Feb 21
The Cheese House
Interior

Willow Cabin

Willow Cabin
3.0 star property
Cowes
The price is P20,663
P24,796 total
includes taxes & fees
Feb 28 - Mar 1
Willow Cabin
Interior

Relax in This Charming East Cowes House With Garden and BBQ

Relax in This Charming East Cowes House With Garden and BBQ
2.0 star property
East Cowes
The price is P17,795
P21,355 total
includes taxes & fees
Mar 7 - Mar 8
Relax in This Charming East Cowes House With Garden and BBQ
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

voco Southampton by IHG

voco Southampton by IHG

10/10 Excellent
"Fab staff and nice room"
Dawn 3-night trip
Posted 2 days ago
voco Southampton by IHG

Find out more about Winsor

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Frequently asked questions

Are there vacation rentals in Winsor?

Yes, we give you a choice of vacation rentals close to the most popular sights in Winsor, or you can select a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals that Winsor has to offer?

The Cliff House Hotel: Visitors like this Winsor vacation home rental. It offers a terrace, a garden, and daily housekeeping to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

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 larger area.

What are vacation rentals like in Winsor?

Vacation rentals are private properties you can book for several days or longer in Winsor. Vacation rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a small group gathering.