Winsor Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Holiday Rentals in Winsor

Our top choices for Winsor holiday rentals

room2 Southampton Hometel
Front of property

room2 Southampton Hometel

4.0 star property
9.4 out of 10, Exceptional, (1064)
"It was perfect for getting to our cruise port here in Southampton. Lovely parks nearby and nice restaurants as well."
The price is HK$875
HK$1,050 total
includes taxes & fees
25 Aug - 26 Aug
room2 Southampton Hometel
Chelsea Hotel
Exterior

Chelsea Hotel

3.0 star property
9.2 out of 10, Wonderful, (81)
"Room was clean and welcoming. I did like the interaction not needed to check in, smart easy and quick way of doing things. I enjoyed it! Room was exactly as stated and advertised. The only thing missing was maybe a chair to sit on. We did not miss out on anything, happy about our stay!"
Chelsea Hotel
The Madison
1 bedroom, premium bedding, individually decorated

The Madison

3.0 star property
9.4 out of 10, Exceptional, (26)
"Stunning property, host was lovely very accomodating quick to respond, would definitely use again, we were working from early hours to late eveming so didn't have chance to shop or eat oit on thia occasion but judging by everything else this host and property offered i would give 10 out of 10 on all "
The Madison
The Walls
Lobby sitting area

The Walls

2.0 star property
4.6 out of 10, (7)
"It was ok for a quick stay. nothing fancy. "
The Walls
Bayview Apartments
Shared kitchen

Bayview Apartments

2.0 star property
7.0 out of 10, Good, (2)
"To be honest although the apartment was really nice we didn’t have hardly any knives and forks and spoons for 5 people, the fridge was filthy and the cooking equipment was old worn out and filthy. For nearly £300 for one night we expected better "
The price is HK$1,401
HK$1,682 total
includes taxes & fees
3 Sept - 4 Sept
Bayview Apartments
Southampton Serviced Apartment
Balcony view

Southampton Serviced Apartment

4.0 star property
8.4 out of 10, Very good, (170)
"It was in a good location. The communication was perfect. "
Southampton Serviced Apartment
Luxury villa, amazing location, pool, jacuzzi, snooker, cinema & tennis court!
Outdoor pool, a heated pool

Luxury villa, amazing location, pool, jacuzzi, snooker, cinema & tennis court!

10.0 out of 10, Exceptional, (46)
"Fantastic stay in the new forest. Great location, really nice property. Absolutely exceeded our expectations. Highly recommend and would stay again!"
Luxury villa, amazing location, pool, jacuzzi, snooker, cinema & tennis court!
Southampton Waterside by Charles Hope
Exterior

Southampton Waterside by Charles Hope

3.0 star property
9.0 out of 10, Wonderful, (11)
"Great location The vue is amazigh!!"
Southampton Waterside by Charles Hope
Pinnacle Suites
1 bedroom, premium bedding, Select Comfort beds, desk

Pinnacle Suites

3.0 star property
9.8 out of 10, Exceptional, (22)
"If I could rate it higher I would. Super friendly, great location, very comfortable rooms (even with AC, a big plus!)"
Pinnacle Suites
The Cliff House Hotel
Exterior

The Cliff House Hotel

4.0 star property
9.4 out of 10, Exceptional, (390)
"Really comfortable room, excellent food in restaurant, good parking and pleasant and friendly staff"
The price is HK$1,489
HK$1,787 total
includes taxes & fees
31 Aug - 1 Sept
The Cliff House Hotel
Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!
Fridge, microwave, oven, stovetop

Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!

9.8 out of 10, Exceptional, (188)
"We had the most wonderful last minute stay. timo was very helpful, available and accomodating. The venue was perfect - spotless and welcoming. Very spacious and beautiful inside and outside, with lovely thoughtful touches. None of us wanted to leave! Thank you Timo"
Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!
Peartree Serviced Apartments
Private kitchen

Peartree Serviced Apartments

3.5 star property
9.6 out of 10, Exceptional, (283)
"Very nice stay and staff. Highly recommended "
The price is HK$1,267
HK$1,520 total
includes taxes & fees
7 Sept - 8 Sept
Peartree Serviced Apartments
Bournemouth Getaway for 14
Fridge, microwave, oven, stovetop

Bournemouth Getaway for 14

9.0 out of 10, Wonderful, (4)
"The house was very spacious, clean and well equipped for our group of 12 and 2 dogs. We had no issues with our stay. I would highly recommend, we had a brilliant time. Thanks Kim"
Bournemouth Getaway for 14
Pamper House Holiday Home And Annex
6 bedrooms, Egyptian cotton sheets, premium bedding, Select Comfort beds

Pamper House Holiday Home And Annex

3.0 star property
Pamper House Holiday Home And Annex
Beautiful 2 bedroom full-furnished semi-detached house with parking
Fridge, microwave, oven, dishwasher

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

9.6 out of 10, Exceptional, (5)
"Everything was perfect!"
The price is HK$1,419
HK$1,587 total
includes taxes & fees
25 Aug - 26 Aug
Beautiful 2 bedroom full-furnished semi-detached house with parking
City Centre Ensuite Rooms--Landmark-Close to Docks/Stadium
Fridge, microwave, oven, coffee/tea maker

City Centre Ensuite Rooms--Landmark-Close to Docks/Stadium

The price is HK$8,041
HK$9,092 total
includes taxes & fees
22 Aug - 23 Aug
City Centre Ensuite Rooms--Landmark-Close to Docks/Stadium
Superyacht on 5* Ocean Village Marina, Southampton
Marina

Superyacht on 5* Ocean Village Marina, Southampton

9.6 out of 10, Exceptional, (7)
"The yacht Ohana is a great place to stay with excellent facilities and in a fab location close to bars and restaurants.A very helpful owner made our weekend perfect! "
The price is HK$2,261
HK$3,028 total
includes taxes & fees
4 Sept - 5 Sept
Superyacht on 5* Ocean Village Marina, Southampton
Premium Double Room with Ensuite
Beach

Premium Double Room with Ensuite

2.0 star property
2.0 out of 10, (1)
"Be very very careful when choosing this flat! The pictures do not match the accommodation at all. The cleanliness leaves much to be desired, the conditions are non-existent and the owner does not inspire trust or safety, as the apartment does not offer either. I do not recommend this place for women. I do not think I have ever met such an unsafe place. Avoid staying here, expedia should remove it from the site."
The price is HK$900
HK$1,878 total
includes taxes & fees
22 Aug - 23 Aug
Premium Double Room with Ensuite
Southampton retreat-Hot Tub-Pool-Parking
Exterior

Southampton retreat-Hot Tub-Pool-Parking

2.0 star property
7.0 out of 10, Good, (2)
"Serene location. Nice property. "
The price is HK$2,444
HK$3,248 total
includes taxes & fees
29 Aug - 30 Aug
Southampton retreat-Hot Tub-Pool-Parking
Family House in Eastleigh
Private kitchen

Family House in Eastleigh

2.0 star property
Family House in Eastleigh
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.
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

Harbour Hotel Southampton

Harbour Hotel Southampton

10/10 Excellent
"From the fabulous staff at check in, to the gorgeous comforts of my cozy double this hotel really is quite special. If it is first class hospitality and modern yet warm luxury you are looking for then this is for you. There is even complementary gin in the room ( shame I was on business) I didn’t make it up to the roof top bar- but hear it’s amazing- but I did sit out on my beautiful balcony over looking the yachts. To finish it off the gym is pretty impressive for a hotel gym !"
Lucy 1-night trip
Posted 10 hours ago
Harbour Hotel Southampton

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?

The Cliff House Hotel: This holiday home rental outside of Winsor offers a terrace, a garden and daily housekeeping to help you feel perfectly comfortable in your new surroundings. This holiday 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 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.