Winsor Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Winsor vacation rentals

Private kitchen
Peartree Serviced Apartments

Aparthotel in Salisbury

Peartree Serviced Apartments
3.5 star property
9.6 out of 10, Exceptional, (305)
"Enjoyable stay, handy to Salisbury landmarks."
Australia
Heather
The price is P5,726
P6,871 total
includes taxes & fees
Feb 1 - Feb 2
Peartree Serviced Apartments
Exterior
The Cliff House Hotel

Vacation Home in New Milton

The Cliff House Hotel
4.0 star property
9.4 out of 10, Exceptional, (404)
"Great location, food, accomodation and pleasant staff."
United Kingdom
Anthony
The price is P11,228
P13,474 total
includes taxes & fees
Jan 8 - Jan 9
The Cliff House Hotel
Free WiFi
Pebbles Guest House - Flat 5

Apartment in Freemantle

Pebbles Guest House - Flat 5
2.0 star property
The price is P2,972
P3,567 total
includes taxes & fees
Jan 14 - Jan 15
Pebbles Guest House - Flat 5
Front of property
room2 Southampton Hometel

Aparthotel in Southampton City Centre

room2 Southampton Hometel
4.0 star property
9.4 out of 10, Exceptional, (1181)
"Staff was great and the room was really nice. I was impressed by the design and it was spacious "
United States
Vanessa
The price is P4,957
P5,948 total
includes taxes & fees
Jan 7 - Jan 8
room2 Southampton Hometel
Premium bedding, Select Comfort beds, desk, laptop workspace
Pinnacle Suites

Aparthotel in Cowes

Pinnacle Suites
3.0 star property
9.8 out of 10, Exceptional, (25)
"Great place to stay. Facilities are very nice and clean. Zoe is a very helpful and kind host. "
Denmark
Sebastian
The price is P10,303
P12,364 total
includes taxes & fees
Jan 9 - Jan 10
Pinnacle Suites
Exterior
Southampton retreat-Hot Tub-Pool-Parking

Apartment in Shirley

Southampton retreat-Hot Tub-Pool-Parking
2.0 star property
7.0 out of 10, Good, (2)
"Serene location. Nice property. "
United Kingdom
Theertha
The price is P7,445
P11,317 total
includes taxes & fees
Jan 6 - Jan 7
Southampton retreat-Hot Tub-Pool-Parking
Living area
Charles Hope Salisbury Centre

Apartment in Salisbury

Charles Hope Salisbury Centre
3.5 star property
9.6 out of 10, Exceptional, (4)
"Great location and well appointed apartment"
Australia
Greg
Charles Hope Salisbury Centre
Interior
5 Yarmouth Cottages

Cottage in Freshwater

5 Yarmouth Cottages
3.5 star property
9.4 out of 10, Exceptional, (3)
"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 P24,118
P28,941 total
includes taxes & fees
Jan 5 - Jan 6
5 Yarmouth Cottages
Free WiFi
Pebbles Guest House - Flat 6

Apartment in Freemantle

Pebbles Guest House - Flat 6
2.0 star property
The price is P2,675
P3,210 total
includes taxes & fees
Jan 14 - Jan 15
Pebbles Guest House - Flat 6
Private kitchen
2 Bed Flat - Sleeps 4 - Parking - Wifi

Apartment in The Polygon

2 Bed Flat - Sleeps 4 - Parking - Wifi
3.0 star property
10.0 out of 10, Exceptional, (1)
"Great apartment, super friendly host!"
United Kingdom
Amy
The price is P19,162
P22,994 total
includes taxes & fees
Jan 10 - Jan 11
2 Bed Flat - Sleeps 4 - Parking - Wifi
Free WiFi
Pebbles Guest House - Flat 7

Apartment in Freemantle

Pebbles Guest House - Flat 7
2.0 star property
The price is P3,567
P4,280 total
includes taxes & fees
Jan 14 - Jan 15
Pebbles Guest House - Flat 7
Interior
4thedome

Apartment in New Milton

4thedome
3.5 star property
9.4 out of 10, Exceptional, (12)
"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 P5,350
P9,194 total
includes taxes & fees
Jan 6 - Jan 7
4thedome
Dining
The Itchen River Apartments

Apartment in Southampton

The Itchen River Apartments
3.5 star property
10.0 out of 10, Exceptional, (1)
"Check-in was quite complicated but the support was good "
United Kingdom
Robert
The price is P11,334
P16,089 total
includes taxes & fees
Jan 10 - Jan 11
The Itchen River Apartments
Marina
Whitfield P10

Cottage in Yarmouth

Whitfield P10
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is P26,004
P31,205 total
includes taxes & fees
Jan 4 - Jan 5
Whitfield P10
Balcony view
Southampton Serviced Apartment

Apartment in Bassett

Southampton Serviced Apartment
4.0 star property
8.4 out of 10, Very Good, (179)
"Ideal, close to Univeristy. "
United Kingdom
Sheena
The price is P9,577
P11,492 total
includes taxes & fees
Jan 6 - Jan 7
Southampton Serviced Apartment
Exterior
Salisbury Residences by Charles Hope

Vacation Home in Salisbury

Salisbury Residences by Charles Hope
4.0 star property
Salisbury Residences by Charles Hope
Marina
Daisy Haven in Southampton

Residence in Bassett Green

Daisy Haven in Southampton
2.0 star property
The price is P12,661
P15,193 total
includes taxes & fees
Jan 11 - Jan 12
Daisy Haven in Southampton
Terrace/patio
Peaceful Elevated Residential Area - Walk to City

Cottage in Winchester

Peaceful Elevated Residential Area - Walk to City
5.0 star property
Peaceful Elevated Residential Area - Walk to City
6 bedrooms, Egyptian cotton sheets, premium bedding, Select Comfort beds
Pamper House Holiday Home And Annex

Vacation Home in Ferndown

Pamper House Holiday Home And Annex
3.0 star property
Pamper House Holiday Home And Annex
Private kitchen
Stonehenge Cottages

Cottage in Salisbury

Stonehenge Cottages
5.0 star property
9.8 out of 10, Exceptional, (105)
"Information, including a video, provided by the friendly owners before and during our stay was excellent. The beautifully appointed cottage was convenient for Salisbury and for the nearby pub which serves good food. We will definitely stay there again, if in the area."
United Kingdom
Fiona
The price is P13,143
P15,772 total
includes taxes & fees
Jan 4 - Jan 5
Stonehenge Cottages
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

Winchester Wessex Hotel by Sunday

Winchester Wessex Hotel by Sunday

10/10 Excellent
"Didn't have breakfast this time"
Fred 2-night trip
Posted 3 days ago
Winchester Wessex Hotel by Sunday

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