Search Holiday Rentals in Winsor

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Top Holiday Rentals in Winsor

Outdoor dining
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
Front of property
room2 Southampton Hometel
4.0 star property
9.6 out of 10, Exceptional, (780)
"We had a great stay here. The accommodations and service were great! I would recommend it. "
The price is £95
per night
23 Jun - 24 Jun
room2 Southampton Hometel
Fridge, microwave, oven, stovetop
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!
Save an average of 15% on thousands of hotels when you're signed in
Studio, 1 Queen Bed | Private kitchen | Fridge, microwave, stovetop, dishwasher
Peartree Serviced Apartments
3.5 star property
9.6 out of 10, Exceptional, (219)
"Ver6 close to the train station."
The price is £134
per night
9 Jun - 10 Jun
Peartree Serviced Apartments
Apartment, 1 King Bed with Sofa bed | Beach
Stunning one Bedroom Apartment in Bournemouth
3.5 star property
Stunning one Bedroom Apartment in Bournemouth
Exterior
The Cliff House
4.0 star property
9.4 out of 10, Exceptional, (340)
"Lovely small hotel. Very friendly staff. Great location by the sea."
The price is £170
per night
20 Jun - 21 Jun
The Cliff House
View from room
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
3 bedrooms, cots/infant beds, WiFi
5* Shorefield Park - Fantastic 3 Bed Lodge (Sleeps 6) - Private WIFI
9.4 out of 10, Exceptional, (78)
"Great lodge, fab location"
5* Shorefield Park - Fantastic 3 Bed Lodge (Sleeps 6) - Private WIFI
Exterior
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
Exterior
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
Cottage, 1 Bedroom (Dormouse) | Terrace/patio
Hazelhurst Farm
4.5 star property
9.6 out of 10, Exceptional, (45)
"We had a great family stay at Hazelhurst Farm. The cottage is absolutely beautiful and fully equipped with everything we needed. The hosts (Hayley and Carl) were also super nice and helpful. We'll definitely come back "
Hazelhurst Farm
Beach nearby
BOURNEMOUTH18 MINUTES WALK TO BEACH, NEAR TOWN CENTRE 1 BED WiFi PARKING SPOT
9.8 out of 10, Exceptional, (59)
"Lovely apartment that was immaculately clean. Whilst we never had cause to meet our host the contact we had by text was friendly and informative. Would definitely stay here again"
BOURNEMOUTH18 MINUTES WALK TO BEACH, NEAR TOWN CENTRE 1 BED WiFi PARKING SPOT
Beach
Idyllic cottage in the heart of the New Forest National Park
9.8 out of 10, Exceptional, (180)
"2nd visit this year we love it Absolutely perfect for us and the dog So clean and everything we needed Easy to walk into Burley Going to try and see if we can squeeze one more visit in this year !"
Idyllic cottage in the heart of the New Forest National Park
Fridge, microwave, oven, stovetop
Karelia - Lovely Log Cabin w/Hot-tub and forest access, sleeps 10
9.8 out of 10, Exceptional, (131)
"Myself and my family had such a lovely time at this lodge. Everything was perfect. It was clean peaceful and in perfect location for everything. The host Timo was so helpful and we really didn't want our time to end. We wouldn't hesitate to recommend or to come back ourselves. Thank you so much for a perfect family getaway"
Karelia - Lovely Log Cabin w/Hot-tub and forest access, sleeps 10
Flat-screen TV
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 £98
per night
27 May - 28 May
Two Bare Feet
Property grounds
Character Victorian Cottage Opposite Common Land within New Forest National Park
9.8 out of 10, Exceptional, (107)
"The accommodation was A* and the best we have experienced. The location was ideal and our communication with the property owner was first class. We would recommend the cottage and hope to return one day."
Character Victorian Cottage Opposite Common Land within New Forest National Park
Beach nearby
The Retreat Holiday Home, Christchurch, Dorset. Family and couple friendly.
9.4 out of 10, Exceptional, (58)
"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.
Fridge, microwave, oven, stovetop
An Idyllic, Family- Friendly Cottage On A Private Estate In Burley
10.0 out of 10, Exceptional, (52)
"aaa"
An Idyllic, Family- Friendly Cottage On A Private Estate In Burley
Private kitchen | Fridge, microwave, oven, electric kettle
Vrbo Property
The price is £140
per night
31 May - 1 Jun
Vrbo Property
Deluxe Room, 1 King Bed | Premium bedding, Select Comfort beds, desk, laptop workspace
Pinnacle Suites
3.0 star property
Pinnacle Suites
Don't see what you're looking for?
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

Bar (on property)
Leonardo Hotel Southampton
4.0 star property
8.2 out of 10, Very good, (1005)
"Enjoyable stay at the very nice hotel. "
The price is £72
per night
9 Jun - 10 Jun
Leonardo Hotel Southampton
Interior entrance
Leonardo Royal Southampton Grand Harbour
4.0 star property
8.2 out of 10, Very good, (1174)
"Staff was friendly and always ready to help Outstanding hotel will definitely stay there again "
The price is £89
per night
27 May - 28 May
Leonardo Royal Southampton Grand Harbour
Exterior
The Winchester Hotel & Spa
4.0 star property
8.2 out of 10, Very good, (1004)
"Clean and friendly property. Near enough walk into town but uphill on the way back."
The price is £101
per night
9 Jun - 10 Jun
The Winchester Hotel & Spa
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 £95 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.

Recent reviews of Winsor properties
Expedia verified reviews