Winsor Vacation Rentals

    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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Winsor

Lovely cottage & garden. 5 min drive from Paultons Park, home of Peppa Pig
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
room2 Southampton Hometel
Front of property
room2 Southampton Hometel
4.0 star property
9.6 out of 10, Exceptional, (791)
"Payment was taken from my card the day before check-in with no prior warning. I had opted for 'pay at property' so it was a big surprise and I barely had enough money in my account for it as me and the other guests were going to split it when we arrived. The room wasnt ready when we arrived but they were very nice about it. The staff were friendly and helpful. I had tried to do the online check-in but there were so many different parts to it that I gave up on it twice. The cleanliness of the...
The price is ￥15,788
per night
Jun 23 - Jun 24
room2 Southampton Hometel
Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!
Fridge, microwave, oven, stovetop
Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!
10.0 out of 10, Exceptional, (168)
"Lovely place but dreadful if you need to communicate while on vacation. We found some very dirty kitchen items and many broken this & that's. Kitchen lamp not working, bedside light buzzing all night, showers need descaling as do not work properly. Etc ..... could do with a proper check over and upgrade. Also, please don't say you have wifi in here on your advert .... it is intermittent at best so be honest and your customers may not feel cheated into choice as we do ....."
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
Sign in
Sign up, it's free
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, (220)
"Loved, loved this place. It was like a home away from home "
The price is ￥21,425
per night
Jun 18 - Jun 19
Peartree Serviced Apartments
Stunning one Bedroom Apartment in Bournemouth
Apartment, 1 King Bed with Sofa bed | Beach
Stunning one Bedroom Apartment in Bournemouth
3.5 star property
Stunning one Bedroom Apartment in Bournemouth
The Cliff House
Exterior
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 ￥28,252
per night
Jun 20 - Jun 21
The Cliff House
Southampton Serviced Apartment
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
5* Shorefield Park - Fantastic 3 Bed Lodge (Sleeps 6) - Private WIFI
3 bedrooms, cribs/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
Hazelhurst Farm
Cottage, 1 Bedroom (Dormouse) | Terrace/patio
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 Lodge By The Lake at Shorefield Holiday Park
Exterior
The Lodge By The Lake at Shorefield Holiday Park
9.8 out of 10, Exceptional, (89)
"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
New Forest cliff top apartment with distant view of the Needles
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
The Retreat Holiday Home, Christchurch, Dorset. Family and couple friendly.
Beach nearby
The Retreat Holiday Home, Christchurch, Dorset. Family and couple friendly.
9.4 out of 10, Exceptional, (58)
"Everything about the property was perfect! Location, cleanliness, the facilities and the information provided by the host. Be sure to check out the Rising Sun Restaurant next door too, one of the nicest Thai meals we’ve ever had!"
The Retreat Holiday Home, Christchurch, Dorset. Family and couple friendly.
BOURNEMOUTH18 MINUTES WALK TO BEACH, NEAR TOWN CENTRE 1 BED WiFi PARKING SPOT
Beach nearby
BOURNEMOUTH18 MINUTES WALK TO BEACH, NEAR TOWN CENTRE 1 BED WiFi PARKING SPOT
9.8 out of 10, Exceptional, (60)
"The apartment was lovely, comfortable & spotlessly clean. Although compact, there was everything we could possibly need for our four night stay. Close to amenities & a nice walk to the beach & pier at Boscombe."
BOURNEMOUTH18 MINUTES WALK TO BEACH, NEAR TOWN CENTRE 1 BED WiFi PARKING SPOT
'The Haven' a luxury apartment close to the Meon Shore coast.
Beach nearby
'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.
Karelia - Luxury Finnish Log Cabin w/Hot-tub
Fridge, microwave, oven, stovetop
Karelia - Luxury Finnish Log Cabin w/Hot-tub
9.8 out of 10, Exceptional, (132)
"The luxurious cabin had everything we wanted for 6 adults and 3 infants. Bedrooms well appointed, although we hadn't realised the mezzanine bedroom was above the one with 2 singles. The bunk bedroom worked well for my son, wife and 3 year old, as he was adjoining their bedroom and so felt secure. Nice to have 2 ensuite bathrooms as well as the third bathroom. Large open living space with well appointed kitchen. Pleasant wooded garden with hot tub and BBQ. Great to be able to walk straight out of...
Karelia - Luxury Finnish Log Cabin w/Hot-tub
Idyllic cottage in the heart of the New Forest National Park
Beach
Idyllic cottage in the heart of the New Forest National Park
10.0 out of 10, Exceptional, (181)
"Lovely cottage very enjoyable short stay close to the village and amenities. Would come back."
Idyllic cottage in the heart of the New Forest National Park
Charles Hope Apartments Southampton
Apartment | Private kitchen | Fridge, microwave, oven, stovetop
Charles Hope Apartments Southampton
3.5 star property
5.8 out of 10, (7)
"The apartment is in a great location and the info you receive is thorough. Make sure you ask for parking though as it is limited. The apartment was very clean. Our door lock came loose and they helped us within 30 minutes which was really good. The only negatives were that the windows are so thin in places you can hear the traffic and the mattresses were a bit firm for us but if we were in Southampton we would definitely book here again. Great customer service and the space is perfect. "
The price is ￥31,072
per night
Jun 9 - Jun 10
Charles Hope Apartments Southampton
Pinnacle Suites
Deluxe Room, 1 King Bed | Premium bedding, Select Comfort beds, desk, laptop workspace
Pinnacle Suites
3.0 star property
Pinnacle Suites
An Idyllic, Family- Friendly Cottage On A Private Estate In Burley
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
Two Bare Feet
Flat-screen TV
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 ￥16,112
per night
Jun 9 - Jun 10
Two Bare Feet
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

Leonardo Hotel Southampton
Bar (on property)
Leonardo Hotel Southampton
4.0 star property
8.2 out of 10, Very Good, (1025)
"Had a lovely stay, perfect location for what we needed. Friendly staff, very comfortable room and bed. Overall a good stay. "
The price is ￥13,461
per night
Jul 7 - Jul 8
Leonardo Hotel Southampton
Leonardo Royal Southampton Grand Harbour
Interior entrance
Leonardo Royal Southampton Grand Harbour
4.0 star property
8.4 out of 10, Very Good, (1213)
"Great starting place of a cruise vacation. Cute little Port community with nice restaurants around."
The price is ￥14,807
per night
Jun 16 - Jun 17
Leonardo Royal Southampton Grand Harbour
Holiday Inn Express Southampton M27 Jct7, an IHG Hotel
Exterior
Holiday Inn Express Southampton M27 Jct7, an IHG Hotel
3.0 star property
8.4 out of 10, Very Good, (1018)
"Nice room "
The price is ￥11,301
per night
Jul 7 - Jul 8
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.

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 vacation rentals in Winsor?

Yes, we give you a choice of vacation rentals where you'll be just 1.4 mi (2.3 km) from Paultons Family Theme Park - Home of Peppa Pig World, giving you a secluded option if you want a quiet place to stay.

What are some of the best vacation home rentals that Winsor has to offer?

The Cliff House: Visitors like this Winsor vacation home rental. It offers a terrace, a garden, and daily housekeeping to help you feel perfectly comfortable in your new surroundings. This vacation 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 larger area.

What are vacation rentals like in Winsor?

Vacation rentals are private properties you can book for several days or longer in Winsor. Vacation rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a small group gathering.

Recent reviews of Winsor properties
Expedia verified reviews

DoubleTree by Hilton Hotel Southampton

DoubleTree by Hilton Hotel Southampton

5/5 Excellent
"This is our 5th stay pre cruise at the Doubletree Hilton, all very clean and service very good. Easy check in. Comfortable clean rooms, this time we stayed half board and evening meal was excellent value for money. Breakfast was good. Do think car parking should be free though for guests staying at the hotel overnight."
A verified traveler stayed at DoubleTree by Hilton Hotel Southampton
Posted 1 day ago
DoubleTree by Hilton Hotel Southampton