Holiday Rentals in Winsor

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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, (807)
"Very clean, well maintained, friendly and helpful staff. Great restaurants and grocery stores within easy walking distance. "
The price is €113
includes taxes & fees
23 Jun - 24 Jun
room2 Southampton Hometel
Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!
9.8 out of 10, Exceptional, (170)
"Perfect for our get together"
Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!
Peartree Serviced Apartments
3.5 star property
9.6 out of 10, Exceptional, (222)
"Great lodging! A very short walk from the train station, and yet very quiet. Smelled fresh, very clean. Our 1 bedroom was terrific. Full kitchen, living space with couch and tall desk table. Bathroom tiny but worked for us…and so clean! Bed was comfy. Front desk person was kind and welcoming. This place was ideal for a one night stay AND would be terrific as a base for several nights while exploring the area. Easy train to Southampton, and also to Bath. Busses that go to Stonehenge. Walking...
The price is €144
includes taxes & fees
30 Jun - 1 Jul
Peartree Serviced Apartments
Stunning one Bedroom Apartment in Bournemouth
3.5 star property
Stunning one Bedroom Apartment in Bournemouth
The Cliff House
4.0 star property
9.4 out of 10, Exceptional, (342)
"Lovely small hotel. Very friendly staff. Great location by the sea."
The price is €202
includes taxes & fees
12 Jul - 13 Jul
The Cliff House
Southampton Serviced Apartment
4.0 star property
8.4 out of 10, Very good, (149)
"Comfortable apartment with lift and free parking "
Southampton Serviced Apartment
5* Shorefield Park - Fantastic 3 Bed Lodge (Sleeps 6) - Private WIFI
9.4 out of 10, Exceptional, (79)
"Stayed with my young family, sister and mum in this extremely well equiped lodge which was situated on a very quiet part of Shorefield holiday park. The lodge was amazing value for money and contained everything needed for a relaxing break. We have stayed at Shorefield before and its a great location with indoor/outdoor pools, steam room, sauna, arcades etc. Amazing break and we will be renting this lodge again!"
5* Shorefield Park - Fantastic 3 Bed Lodge (Sleeps 6) - Private WIFI
The Lodge By The Lake at Shorefield Holiday Park
9.8 out of 10, Exceptional, (90)
"Great location . Very relaxing. Close to wooded walk . About 10min walk to on site facilities. Good parking."
The Lodge By The Lake at Shorefield Holiday Park
Hazelhurst Farm
4.5 star property
9.6 out of 10, Exceptional, (45)
"Cute and stylish cottage (we were in the Milking Parlour), easy to find and good location. Cosy for a few days for a couple but the outside space a bit disappointing. Inside the cottage is pretty much exactly as per the photos. It's stylish and cleverly designed for multi-functional self-catering. Even has a dishwasher! Some tea, coffee beans, sugar, milk and olive oil kindly provided. The smart home features for air-con, heating, radio etc take getting used to but are effective. Could do with...
Hazelhurst Farm
The Retreat Holiday Home, Christchurch, Dorset. Family and couple friendly.
9.4 out of 10, Exceptional, (59)
"This was a very clean, updated and well equipped property in a quiet close. We enjoyed our stay."
The Retreat Holiday Home, Christchurch, Dorset. Family and couple friendly.
New Forest cliff top apartment with distant view of the Needles
9.6 out of 10, Exceptional, (137)
"It was all we wanted, great location"
New Forest cliff top apartment with distant view of the Needles
'The Haven' a luxury apartment close to the Meon Shore coast.
10.0 out of 10, Exceptional, (202)
"Great place, homely, spotless, great location, we loved our week here"
'The Haven' a luxury apartment close to the Meon Shore coast.
BOURNEMOUTH18 MINUTES WALK TO BEACH, NEAR TOWN CENTRE 1 BED WiFi PARKING SPOT
9.8 out of 10, Exceptional, (62)
"Very clean and tidy property .Nice walk to the seafront."
BOURNEMOUTH18 MINUTES WALK TO BEACH, NEAR TOWN CENTRE 1 BED WiFi PARKING SPOT
Two Bare Feet
3.5 star property
9.2 out of 10, Wonderful, (32)
"Thoroughly enjoyed the independence that Two Bare Feet gave me Staying in conventional hotels around the country can become a chore. Its location with its five minute walk into the city centre makes it ideal The facilities and cleanliness were second to none. Only thing to let it down is the lack of property parking but overnight parking is around £7.30 a night and is an inconvenience not ideal for everyone. That said I would recommend it and would certainly stay there again Many thanks again...
The price is €116
includes taxes & fees
23 Jun - 24 Jun
Two Bare Feet
Character Victorian Cottage Opposite Common Land within New Forest National Park
9.8 out of 10, Exceptional, (109)
"Lovely cottage, clean, quiet residential area close to Lymington centre"
Character Victorian Cottage Opposite Common Land within New Forest National Park
Karelia - Lovely Log Cabin w/Hot-tub and forest access, sleeps 10
9.8 out of 10, Exceptional, (133)
"The property was in a lovely location with walks directly onto the forest. Everything was lovely and clean. Lovely garden too. The host was very prompt with communication and very helpful. Would go again. Thank you."
Karelia - Lovely Log Cabin w/Hot-tub and forest access, sleeps 10
Charles Hope Apartments Southampton
3.5 star property
6.0 out of 10, (8)
"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."
The price is €190
includes taxes & fees
21 Jun - 22 Jun
Charles Hope Apartments Southampton
Pinnacle Suites
3.0 star property
Pinnacle Suites
Vrbo Property
The price is €142
includes taxes & fees
20 Jun - 21 Jun
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.

Other types of properties in Winsor you may be interested in

Leonardo Hotel Southampton
4.0 star property
8.2 out of 10, Very good, (1012)
"Great stay"
The price is €100
includes taxes & fees
7 Jul - 8 Jul
Leonardo Hotel Southampton
Leonardo Royal Southampton Grand Harbour
4.0 star property
8.4 out of 10, Very good, (1225)
"Great for before or after cruise out of Southampton. Crew was excellent "
The price is €95
includes taxes & fees
14 Jul - 15 Jul
Leonardo Royal Southampton Grand Harbour
Holiday Inn Express Southampton M27 Jct7, an IHG Hotel
3.0 star property
8.4 out of 10, Very good, (1013)
"Close to west end. Nice shops. If your into cricket then your in luck. Cheap-ish rooms for cruise times. "
The price is €69
includes taxes & fees
30 Jun - 1 Jul
Holiday Inn Express Southampton M27 Jct7, an IHG Hotel
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 €113 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: 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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