Search Holiday Rentals in Winsor

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Top Holiday Rentals in Winsor

Lovely cottage & garden. 5 min drive from Paultons Park, home of Peppa Pig
9.4 out of 10, Exceptional, (112)
"We had a lovely time. We were staying to visit Paultons park and it was a 7 minute drive away. The cottage is spacious and well equipped. Beds were comfortable. Would book again"
Lovely cottage & garden. 5 min drive from Paultons Park, home of Peppa Pig
room2 Southampton Hometel
4.0 star property
9.6 out of 10, Exceptional, (763)
"The decor was original and imaginative. Marine theme. Loved it. Staff were friendly and helpful. Nothing to not like."
The price is £85
includes taxes & fees
6 May - 7 May
room2 Southampton Hometel
Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!
10.0 out of 10, Exceptional, (166)
"We travelled to Thatch Cottage for a three night stay for my 50th birthday extravaganza. The communication with our hosts as excellent and the check-in process was simple. The property is amazing and the facilities were perfect for our needs. The local area is lovely with plenty of things to do for all ages and interests and the property is the perfect base if you just want to relax. Thank you to Susanna, Steven & Timo for making my birthday everything I wanted, and very much needed, after an...
Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!
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Peartree Serviced Apartments
3.5 star property
9.6 out of 10, Exceptional, (217)
"Really lovely apartment, everything we needed for one overnight stay. Highly recommended "
The price is £136
includes taxes & fees
9 May - 10 May
Peartree Serviced Apartments
Stunning one Bedroom Apartment in Bournemouth
3.5 star property
Stunning one Bedroom Apartment in Bournemouth
5* Shorefield Park - Fantastic 3 Bed Lodge (Sleeps 6) - Private WIFI
9.4 out of 10, Exceptional, (77)
"Lovely clean family friendly property, well equipped kitchen. Catered for a variety of ages and perfectly located on site for easy access to the pool and entertainment as well as access to the beach and clifftop walks. The host was very helpful and quick to respond to any questions. Would definitely consider staying here again."
5* Shorefield Park - Fantastic 3 Bed Lodge (Sleeps 6) - Private WIFI
The Cliff House Hotel
4.0 star property
9.4 out of 10, Exceptional, (338)
"My wife and I stayed at The Cliff House for three nights and had a good time. The staff were all friendly and helpful and the food was superb, especially the "Full Works" breakfast which was cooked to order."
The price is £135
includes taxes & fees
2 May - 3 May
The Cliff House Hotel
New Forest cliff top apartment with distant view of the Needles
9.6 out of 10, Exceptional, (134)
"Nice well equipped apartment. Warm, easily adjustable thermostat. Good size shower. WiFi patchy, though owner was looking into this, really good prompt communication with them."
New Forest cliff top apartment with distant view of the Needles
The Lodge By The Lake at Shorefield Holiday Park
9.8 out of 10, Exceptional, (88)
"Lovely little place,as the name suggests right next to the lake!Great location,close to both the coast & forest. Dogs loved it,would definitely recommend 👍👍"
The Lodge By The Lake at Shorefield Holiday Park
Southampton Serviced Apartment
4.0 star property
8.4 out of 10, Very good, (148)
"Comfortable apartment with lift and free parking "
Southampton Serviced Apartment
'The Haven' a luxury apartment close to the Meon Shore coast.
10.0 out of 10, Exceptional, (199)
"It is a lovely property. We are able to park outside and as soon as you walk in a lovely smell and so clean, warm and welcoming. It is ideal for us as family and friends are just around the corner and the hosts are lovely too."
'The Haven' a luxury apartment close to the Meon Shore coast.
Bright and light 3 bedroom house central Southampton
The price is £139
includes taxes & fees
2 May - 3 May
Bright and light 3 bedroom house central Southampton
BOURNEMOUTH18 MINUTES WALK TO BEACH, NEAR TOWN CENTRE 1 BED WiFi PARKING SPOT
9.8 out of 10, Exceptional, (56)
"Everything about our stay was perfect. The hosts were informative, friendly and on hand. We didn’t need to ask anything about the rooms as it was all as it should be. They saved us lots of time by pointing out the quickest way to get to where we wanted to go."
BOURNEMOUTH18 MINUTES WALK TO BEACH, NEAR TOWN CENTRE 1 BED WiFi PARKING SPOT
Karelia - Lovely Log Cabin w/Hot-tub and forest access, sleeps 10
9.8 out of 10, Exceptional, (129)
"Really good spot, secluded, but close to loads of things to do - wish we’d booked for longer."
Karelia - Lovely Log Cabin w/Hot-tub and forest access, sleeps 10
Charming 17c Grade II listed detached cottage, period features in rural Dorset
7.8 out of 10, Good, (116)
"If you are looking from an away from it all bolt hole then this is for you. Full of charm Nice welcome from Dean Info pack would have been useful"
Charming 17c Grade II listed detached cottage, period features in rural Dorset
Charles Hope Apartments Southampton
3.5 star property
5.8 out of 10, (6)
"Found it very hard to get into property had to call operator a number of times for help, then could not get into flat again needed assistance. Flat door would not lock in the mornings as code would not work so had to take my luggage with me every morning, ( 3 days ) would not stay here again. "
The price is £151
includes taxes & fees
2 May - 3 May
Charles Hope Apartments Southampton
Two Bare Feet
3.5 star property
9.2 out of 10, Wonderful, (32)
"Beautiful property with every thing you could need. Complimentary eggs butter milk bread and fruit a lovely touch and very welcome. We would highly recommend 2 bare feet. Short walk into the town centre. Absolutely perfect. 5 star."
The price is £98
includes taxes & fees
2 May - 3 May
Two Bare Feet
The Retreat Holiday Home, Christchurch, Dorset. Family and couple friendly.
9.2 out of 10, Wonderful, (57)
"Very nice stay in this hidden gem. Had everything we needed, clean and spacious. One word of caution if you have a big car the entrance is tight but you do have an allocated parking place right outside. Would stay again"
The Retreat Holiday Home, Christchurch, Dorset. Family and couple friendly.
Pinnacle Suites
3.0 star property
Pinnacle Suites
Vrbo Property
The price is £140
includes taxes & fees
8 May - 9 May
Vrbo Property
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See all available properties in Winsor
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.

Winsor Holiday Rental Travel Info

Number of holiday rentals
53
Popular accommodation
Winsor cottages
Known landmarks
Mayflower Theatre, New Forest Wildlife Park and Solent Sky Museum
International airport
Southampton (SOU)

Other types of properties in Winsor you may be interested in

Leonardo Royal Southampton Grand Harbour
4.0 star property
8.2 out of 10, Very good, (1149)
"Nice hotel needs a bit of updating the shower needs upgrading as wasn’t very hot or powerful doors and door frames and wardrobe need replacing or painting to keep it up to date "
The price is £77
includes taxes & fees
19 May - 20 May
Leonardo Royal Southampton Grand Harbour
Leonardo Hotel Southampton - Formerly Jurys Inn
4.0 star property
8.2 out of 10, Very good, (1001)
"We stayed 2 nites pre cruise on Queen Mary 2. We ate twice in the restaurant and food was tasty. Our room was comfortable and the front desk young lady, Rakshya?, was most pleasant and helpful"
The price is £72
includes taxes & fees
19 May - 20 May
Leonardo Hotel Southampton - Formerly Jurys Inn
Novotel Southampton
4.0 star property
7.8 out of 10, Good, (1000)
"Amazing staff and so relaxing coming back for next work trip thankyou! "
The price is £76
includes taxes & fees
6 May - 7 May
Novotel Southampton
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.

Everything you need to know about Winsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winsor holiday rentals we have selected for you start as low as £85 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winsor rentals

At Expedia, we put the best Winsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Winsor?

Yes, there are holiday rentals where you'll be just 1.4 mi (2.3 km) from Paultons Family Theme Park - Home of Peppa Pig World, offering you a secluded option if you want a quieter place to 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.

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