Winsor Holiday Rentals

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Holiday Rentals in Winsor

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!
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
Beach nearby
'The Haven' a luxury apartment close to the Meon Shore coast.
10.0 out of 10, Exceptional, (200)
"We needed a place to stay while moving house and found The Haven to be spacious and comfortable. It had everything we needed, including very pleasant hosts. Would not hesitate to recommend and would stay again. Thank you, Trudy and Dean."
'The Haven' a luxury apartment close to the Meon Shore coast.
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Exterior
5-bed house: pool, tennis court, walk to beach, 10 acres
10.0 out of 10, Exceptional, (48)
"Home from home with fantastic grounds lots to do for all ages. Swimming pool was amazing the whole family spent hours outside and the teenagers weren't on their phones. We will be back next year hopefully"
5-bed house: pool, tennis court, walk to beach, 10 acres
Beach
Hidden Gem - 3 Bedroom Apartment minutes to High Street & Beaches
10.0 out of 10, Exceptional, (13)
"Had a really nice time, the apartment was nicer than we expected and was very clean. Host was extremely responsive, we left an item in the property and they have been very accommodating in order to arrange collection of the item."
Hidden Gem - 3 Bedroom Apartment minutes to High Street & Beaches
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
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
Property grounds
Character Victorian Cottage Opposite Common Land within New Forest National Park
9.8 out of 10, Exceptional, (107)
"Wonderful little cottage, very clean and comfortable. It has everything you would need for a break away. Superb to have a huge park opposite in which to walk the dogs. Mick the property manager even left us a cake for our arrival which was very much appreciated. Would recommend"
Character Victorian Cottage Opposite Common Land within New Forest National Park
Property grounds
Remodelled historical cottage, super location, w/hottub
9.8 out of 10, Exceptional, (23)
"This was a lovely property in a beautiful location. The garden was great for the two dogs that we brought. The host showed us around when we arrived and said if we needed anything just to ring this was comforting. The only slight draw back was it could have been a little cleaner in fact there were a pair of knickers under one of the beds presumably left by a previous tenant!"
Remodelled historical cottage, super location, w/hottub
Sun-loungers
A beautiful cottage in the heart of the New Forest and a short drive to beaches
9.8 out of 10, Exceptional, (75)
"We had a wonderful trip. Thanku to our host Nicky who was very kind and helpful!"
A beautiful cottage in the heart of the New Forest and a short drive to beaches
Tranquil Cottage in this Quiet Corner of The New Forest.
9.8 out of 10, Exceptional, (234)
"A fantastic location, peaceful but local pubs and restaurants are nearby, check in process was fantastic. We cannot fault the accommodation"
Tranquil Cottage in this Quiet Corner of The New Forest.
Front of property
room2 Southampton Hometel
4.0 star property
9.6 out of 10, Exceptional, (780)
"Beautiful views of the park/water. WhatsApp communication was unsuccessful however the atmosphere, staff and surrounding areas made it a worthwhile stay. "
The price is NZ$207
includes taxes & fees
16 Jun - 17 Jun
room2 Southampton Hometel
Studio, 1 Queen Bed | Private kitchen
Peartree Serviced Apartments
3.5 star property
9.6 out of 10, Exceptional, (219)
"Lovely apartment with a continental breakfast in the kitchen when we arrived, Didn’t see any of the reception staff as we did self check in and key drop off, We would definitely stay here again "
The price is NZ$262
includes taxes & fees
3 Jun - 4 Jun
Peartree Serviced Apartments
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
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
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 NZ$355
includes taxes & fees
20 Jun - 21 Jun
The Cliff House
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
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.

Other types of properties in Winsor you may be interested in

Exterior
Holiday Inn Express Southampton M27 Jct7, an IHG Hotel
3.0 star property
8.4 out of 10, Very good, (1003)
"Employees were amazing location was great "
The price is NZ$133
includes taxes & fees
9 Jun - 10 Jun
Holiday Inn Express Southampton M27 Jct7, an IHG Hotel
Bar (on property)
Leonardo Hotel Southampton
4.0 star property
8.2 out of 10, Very good, (1003)
"very friendly staff. Didn't like that you couldn't pay cash for anything. The breakfast when converted into Canadian dollars was very expensive almost $40.00. I would stay there again and have breakfast somewhere else."
The price is NZ$152
includes taxes & fees
23 Jun - 24 Jun
Leonardo Hotel Southampton
Interior entrance
Leonardo Royal Southampton Grand Harbour
4.0 star property
8.2 out of 10, Very good, (1171)
"We were grateful, through inquiry of our local cousin, to receive a room upgrade with a balcony and view making our experience all the more special. It was easy to be satisfied because of the care and attention received from staff. They were friendly, warm and responsive. It’s very easy to say we would stay here again on a return trip"
The price is NZ$167
includes taxes & fees
23 Jun - 24 Jun
Leonardo Royal Southampton Grand Harbour
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winsor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winsor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winsor. Seeing all the best attractions is bound to make you fall in love with Winsor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winsor short-term rentals, that won’t be hard to do.

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