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Check prices for these dates

In two weeks
19 Sep - 21 Sep
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Top 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, (1091)
"Fabulous property. Would stay again for certain. Great staff and room and location "
The price is ฿2,676
฿3,211 total
includes taxes & fees
5 Oct - 6 Oct
room2 Southampton Hometel
The Madison
Superior Studio | 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
Southampton Serviced Apartment
Balcony view

Southampton Serviced Apartment

4.0 star property
8.4 out of 10, Very good, (171)
"It was in a good location. The communication was perfect. "
Southampton Serviced Apartment
The Cliff House Hotel
Exterior

The Cliff House Hotel

4.0 star property
9.4 out of 10, Exceptional, (392)
"Really comfortable room, excellent food in restaurant, good parking and pleasant and friendly staff"
The price is ฿6,139
฿7,367 total
includes taxes & fees
7 Sept - 8 Sept
The Cliff House Hotel
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 ฿2,347
฿2,817 total
includes taxes & fees
14 Sept - 15 Sept
Chelsea Hotel
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 ฿5,778
฿6,934 total
includes taxes & fees
16 Sept - 17 Sept
Bayview Apartments
Pinnacle Suites
Deluxe Room, 1 Double Bed, Harbour View | 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 Cabin at Little Timbers
Outdoor dining

The Cabin at Little Timbers

3.0 star property
The price is ฿13,037
฿15,645 total
includes taxes & fees
20 Sept - 21 Sept
The Cabin at Little Timbers
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 ฿10,477
฿12,573 total
includes taxes & fees
10 Sept - 11 Sept
Charming 2-bed Apartment in Central Southampton
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, (286)
"Very nice stay and staff. Highly recommended "
The price is ฿4,653
฿5,584 total
includes taxes & fees
5 Oct - 6 Oct
Peartree Serviced Apartments
The Walls
Lobby sitting area

The Walls

2.0 star property
5.8 out of 10, (9)
"It was ok for a quick stay. nothing fancy. "
The Walls
CityLivein Bournemouth
Courtyard

CityLivein Bournemouth

6.0 out of 10, (30)
CityLivein Bournemouth
Family House in Eastleigh
House | Private kitchen | Fridge, microwave, oven, stovetop

Family House in Eastleigh

2.0 star property
Family House in Eastleigh
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 ฿6,000
฿6,650 total
includes taxes & fees
16 Sept - 17 Sept
Oceanview Gem in Southampton
Charles Hope Salisbury Centre
Family Apartment | Living area | Flat-screen TV

Charles Hope Salisbury Centre

3.5 star property
9.0 out of 10, Wonderful, (2)
"The property is updated and clean. It's close to shopping and eateries. The only negative comment I have is that their website needs to update how to enter the apartment. Instead of stating to enter code and push door, tell patrons to enter door and turn knob while the button on the knob is still green. It was, honestly, a bit confusing. Other than that, everything was excellent!"
Charles Hope Salisbury Centre
15 Rosewood
Electric kettle, toaster, cookware/dishes/utensils

15 Rosewood

3.0 star property
The price is ฿15,493
฿18,592 total
includes taxes & fees
12 Sept - 13 Sept
15 Rosewood
Bailey Cottage
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Bailey Cottage

3.0 star property
The price is ฿52,727
฿63,272 total
includes taxes & fees
10 Sept - 11 Sept
Bailey Cottage
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 ฿7,426
฿10,872 total
includes taxes & fees
15 Sept - 16 Sept
Peaceful Retreat in Southampton's Countryside
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. "
Southampton retreat-Hot Tub-Pool-Parking
Beddoe Apartments
Miscellaneous

Beddoe Apartments

3.0 star property
8.2 out of 10, Very good, (19)
"Ideal for couple of nights stay. Easy parking was a bonus. "
The price is ฿10,473
฿14,518 total
includes taxes & fees
7 Sept - 8 Sept
Beddoe Apartments
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

Find out more about Winsor

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
  • Use the map to find apartments and other holiday homes in the Winsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winsor while they last

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

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.