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Check prices for these dates

Tonight
29 Jul - 30 Jul
Tomorrow
30 Jul - 31 Jul
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Top Holiday Rentals in Winsor

room2 Southampton Hometel
Front of property

room2 Southampton Hometel

4.0 star property
9.4 out of 10, Exceptional, (1046)
"Great place we really liked it"
The price is ฿3,058
฿3,669 total
includes taxes & fees
10 Aug - 11 Aug
room2 Southampton Hometel
Pinnacle Suites
Deluxe Room, 1 Double Bed, Harbour View | 1 bedroom, premium bedding, Select Comfort beds, desk

Pinnacle Suites

3.0 star property
9.6 out of 10, Exceptional, (20)
"Had a great time here, in town for a wedding. The location is perfect and right off the red jet ferry. Zoe was also super helpful "
Pinnacle Suites
Chelsea Hotel
Exterior

Chelsea Hotel

3.0 star property
9.2 out of 10, Wonderful, (81)
"Overall a good place to stay."
The price is ฿3,627
฿4,352 total
includes taxes & fees
22 Aug - 23 Aug
Chelsea Hotel
The Walls
Lobby sitting area

The Walls

2.0 star property
4.0 out of 10, (3)
"It was ok for a quick stay. nothing fancy. "
The price is ฿1,259
฿3,246 total
includes taxes & fees
3 Aug - 4 Aug
The Walls
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
The Madison
Superior Studio | 1 bedroom, premium bedding, individually decorated

The Madison

3.0 star property
9.4 out of 10, Exceptional, (25)
"A walkable distance to the city center."
The Madison
Bayview Apartments
Shared kitchen

Bayview Apartments

2.0 star property
8.0 out of 10, Very good, (1)
"Nice apartment. "
The price is ฿5,786
฿6,943 total
includes taxes & fees
6 Aug - 7 Aug
Bayview Apartments
Peartree Serviced Apartments
Studio, 1 Queen Bed | Private kitchen | Fridge, microwave, stovetop, dishwasher

Peartree Serviced Apartments

3.5 star property
9.6 out of 10, Exceptional, (282)
"Very nice stay and staff. Highly recommended "
The price is ฿4,668
฿5,601 total
includes taxes & fees
3 Aug - 4 Aug
Peartree Serviced Apartments
The Cliff House Hotel
Exterior

The Cliff House Hotel

4.0 star property
9.4 out of 10, Exceptional, (388)
"The staff were great friendly and helpful The bar and restaurant were very good and the surrounding areas were lovely "
The price is ฿6,165
฿7,398 total
includes taxes & fees
10 Aug - 11 Aug
The Cliff House Hotel
Southampton Serviced Apartment
Balcony view

Southampton Serviced Apartment

4.0 star property
8.4 out of 10, Very good, (167)
"It was in a good location. The communication was perfect. "
Southampton Serviced Apartment
Pamper House Holiday Home And Annex
Luxury House | 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
Oceanview Gem in Southampton
Apartment | Private kitchen | Fridge, microwave, oven, stovetop

Oceanview Gem in Southampton

3.0 star property
2.0 out of 10, (1)
"The host never responded to any communications. I tried calling, SMS, email and hotel.com chat. The agent also tried to contact them unsuccessfully. I had to wait until 4pm on the day of arrival before the agent agreed to re-book. After that I then had to wait for hotels.com to respond. Gave up and asked for a refund. These people will leave you oit of pocket, on the street, in the dark. Dangerous and unethical practice especially for lone female travellers."
The price is ฿6,008
฿6,659 total
includes taxes & fees
1 Aug - 2 Aug
Oceanview Gem in Southampton
Charles Hope Apartments Southampton
Two Bedroom Apartment | Private kitchen | Fridge, microwave, oven, stovetop

Charles Hope Apartments Southampton

3.5 star property
7.0 out of 10, Good, (12)
"Property was clean, good location, near the cruise ports, restraunts, coffee shops. It was difficult for us to get into the building initially as we arrived later. But we got in touch with contact number and spoke with someone who arranged entry to building front door."
Charles Hope Apartments Southampton
Family House in Eastleigh
House | Private kitchen | Fridge, microwave, oven, stovetop

Family House in Eastleigh

2.0 star property
The price is ฿5,777
฿6,862 total
includes taxes & fees
3 Aug - 4 Aug
Family House in Eastleigh
Dorset Explorers
Fridge, dishwasher, electric kettle, toaster

Dorset Explorers

3.0 star property
Dorset Explorers
Charming 2-bed Apartment in Central Southampton
Apartment | Private kitchen | Fridge, microwave, oven, stovetop

Charming 2-bed Apartment in Central Southampton

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great apartment, super friendly host!"
The price is ฿10,491
฿12,590 total
includes taxes & fees
3 Aug - 4 Aug
Charming 2-bed Apartment in Central Southampton
Peaceful Retreat in Southampton's Countryside
Bungalow, 2 Bedrooms, Patio, City View | Property grounds

Peaceful Retreat in Southampton's Countryside

2.0 star property
The price is ฿7,416
฿10,864 total
includes taxes & fees
11 Aug - 12 Aug
Peaceful Retreat in Southampton's Countryside
Holiday Home With Hot Tub & Sauna
Property amenity

Holiday Home With Hot Tub & Sauna

4.0 star property
9.4 out of 10, Exceptional, (3)
" What the full holiday with my kids thanks guys"
The price is ฿17,626
฿28,985 total
includes taxes & fees
14 Aug - 15 Aug
Holiday Home With Hot Tub & Sauna
Luxury Shepherds Hut set in a Countryside Setting
Cabin | Terrace/patio

Luxury Shepherds Hut set in a Countryside Setting

2.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing stay, great-friendly customer service. Everything been well thought out everything included definitely worth a stay . Highly recommended. "
Luxury Shepherds Hut set in a Countryside Setting
CityLivein Bournemouth
Courtyard

CityLivein Bournemouth

6.0 out of 10, (30)
CityLivein Bournemouth
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

Meon Valley Hotel, Golf & Country Club

Meon Valley Hotel, Golf & Country Club

10/10 Excellent
"This is the second time staying at the hotel and it’s been very good, the only areas that could be improved are the breakfast selection and the rooms having air conditioning. "
Usman 2-night trip
Posted 1 day ago
Meon Valley Hotel, Golf & Country Club

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.