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Winsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winsor vacation rentals

A modern interior with a red sofa, black chairs, and a patterned floor.

1. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,355 reviews)
"Great location and friendly staff!"
United States
Gary
The price is CA $122
CA $146 total
includes taxes & fees
Nov 10 - Nov 11
Second Nature Southampton
A paved driveway leading to a wooden gate, a bicycle with a bag, and a shed in a garden setting.

2. Beautiful New Forest Hideaway

Beautiful New Forest Hideaway
West Wellow
10.0 out of 10, Exceptional, (2 reviews)
"Lovely cottage!! Clean and had everything you could possibly need!! Our stay was so relaxing we didn’t want to leave and will be back soon !!"
United States
Alena M.
The price is CA $235
CA $330 total
includes taxes & fees
Oct 14 - Oct 15
Beautiful New Forest Hideaway
A bedroom with a large bed, a wooden ceiling, and a view of a brick building outside.

3. Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.0 out of 10, Very good, (12 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is CA $91
CA $194 total
includes taxes & fees
Nov 8 - Nov 9
Settle Southampton
A corner room with a large window overlooking a city street and buildings.

4. Ocean Quay Luxury - Stylish 2 Bed - Has Parking

Ocean Quay Luxury - Stylish 2 Bed - Has Parking
3.0 star property
Southampton City Centre
Ocean Quay Luxury - Stylish 2 Bed - Has Parking
An outdoor patio with wooden furniture, a table set for dining, and a pergola with climbing plants.

5. New Forest National Park Studio @Forest Palms

New Forest National Park Studio @Forest Palms
Hyde
10.0 out of 10, Exceptional, (10 reviews)
"We loved it! It was very clean, comfy and welcoming. The garden had lovely flowers. We enjoyed the very nice pool as well. It was a little piece of paradise in a lovely area of England. We hope to come back again soon."
Germany
Dan R.
The price is CA $223
CA $302 total
includes taxes & fees
Oct 14 - Oct 15
New Forest National Park Studio @Forest Palms
A row of wooden cabins with attached porches, each with a small porch light.

6. Farm Cottage on a Secluded 9-acre Equestrian Small Holding

Farm Cottage on a Secluded 9-acre Equestrian Small Holding
Salisbury
10.0 out of 10, Exceptional, (17 reviews)
"Lovely accommadition all you could need for a get away, we only stayed 1 night wish it could have been more. Only issue main entrance is rather secluded.Hope to return for a longer stay, peaceful and secluded"
United States
Diana T.
The price is CA $287
CA $326 total
includes taxes & fees
Nov 3 - Nov 4
Farm Cottage on a Secluded 9-acre Equestrian Small Holding
A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a radiator.

7. Settle Winchester

Settle Winchester
2.0 star property
Winchester City Center
The price is CA $58
CA $172 total
includes taxes & fees
Nov 8 - Nov 9
Settle Winchester
A bedroom with a large bed, a sofa, a TV, and a window with blinds.

8. QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
5.8 out of 10, (17 reviews)
"They sent me an email at the last minute saying that it was double booked and they canceled my reservation that was already prepaid"
United States
kia
The price is CA $289
CA $346 total
includes taxes & fees
Oct 14 - Oct 15
QE2 Loft Apartments
A modern living room with a sofa, ottoman, and a coffee table with flowers. There is a fireplace, a television, and a kitchen area visible.

9. 7 Wild Haven

7 Wild Haven
3.0 star property
Salisbury
The price is CA $823
CA $987 total
includes taxes & fees
Nov 1 - Nov 2
7 Wild Haven
A calm lake with ducks and a swan, a boat docked on the left, and a building in the background.

10. Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton

Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton
Portswood
10.0 out of 10, Exceptional, (1 review)
"We had a great time, lovely neighborhood, location is easy access to needed items. Marvin is an excellent host. He responds right away with all questions. For a home that is 140 years old it is in excellent shape. Beautifully decorated. Everything we needed was there. Big plus to be on the water. Thank you Marvin!"
United States
Terri M.
The price is CA $221
CA $275 total
includes taxes & fees
Oct 21 - Oct 22
Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton
A wooden cabin with an open door revealing a kitchen area, two wicker chairs, and a small wooden table.

11. Luxury shepherd's hut

Luxury shepherd's hut
Bransgore
9.8 out of 10, Exceptional, (43 reviews)
"We had the best stay in this beautiful shepherds hut. The location was perfect, the position of the shepherds hut allowed for guest privacy while also offering wonderful views and outdoor space. The accommodation was perfect with everything you could need. Would highly recommend. "
United Kingdom
Hayley M.
The price is CA $287
CA $325 total
includes taxes & fees
Oct 15 - Oct 16
Luxury shepherd's hut
A coastal beach with a rocky cliff and a clear view of the sea.

12. Unique detached holiday cottage, Hampshire

Unique detached holiday cottage, Hampshire
Sopley
9.8 out of 10, Exceptional, (84 reviews)
"Great place for a short stay"
United Kingdom
Keiron D.
The price is CA $166
CA $264 total
includes taxes & fees
Oct 15 - Oct 16
Unique detached holiday cottage, Hampshire
A modern kitchen with a central island, bar stools, hanging plants, and a variety of appliances.

13. Adorable 2-bedroom apartment in Southampton

Adorable 2-bedroom apartment in Southampton
Freemantle
9.0 out of 10, Wonderful, (4 reviews)
"Apartment was in great condition, no complaints!"
United Kingdom
Bethany M.
The price is CA $267
CA $348 total
includes taxes & fees
Oct 18 - Oct 19
Adorable 2-bedroom apartment in Southampton
A room with a dartboard, a power outlet, a potted plant, and a curtain.

14. 4 Bedrooms - The Family Haven With Parking Near Airport

4 Bedrooms - The Family Haven With Parking Near Airport
3.0 star property
Eastleigh
The price is CA $258
CA $309 total
includes taxes & fees
Nov 1 - Nov 2
4 Bedrooms - The Family Haven With Parking Near Airport
A mobile home with a white exterior, a deck with white railings, and a black roof vent labeled "ABI 50A".

15. New Forest & coastal retreat

New Forest & coastal retreat
New Milton
10.0 out of 10, Exceptional, (4 reviews)
"The caravan was spotlessly clean and we had everything we needed for our stay. The shower leaked a bit and was difficult to control the temperature but no biggy really. We paid extra for passes to the site facilities. We used the clubhouse for food and drinks, pool etc. well worth the little extra. Alison was a great host with quick and easy communication. Would recommend "
United States
Al D.
The price is CA $272
CA $355 total
includes taxes & fees
Oct 27 - Oct 28
New Forest & coastal retreat
A sign for Hotel Peartree, a serviced apartment, with contact information and website.

16. Peartree Serviced Apartments

Peartree Serviced Apartments
3.5 star property
Salisbury
9.6 out of 10, Exceptional, (327 reviews)
"Great. They have everything you could need - well appointed kitchen, milk and breakfast provided, plenty of fluffy towels even down to non stick bath mats"
Australia
Stephanie
The price is CA $183
CA $220 total
includes taxes & fees
Nov 9 - Nov 10
Peartree Serviced Apartments
A modern kitchen with a built-in island, a sink, and a clock on the wall.

17. 4thedome

4thedome
3.5 star property
New Milton
9.4 out of 10, Exceptional, (13 reviews)
"Lovely peaceful location just around the corner from the beach. Small shop, cafes and bar near by, we’d recommend a visit to the ice cream parlour - lots of flavours with vegan and doggy options. The accommodation was spotlessly clean, comfortable and well equipped. Check-in was seamless and the host responded quickly to all communications. Only downside was no enclosed outside space for our dogs"
United Kingdom
Ceri
The price is CA $157
CA $255 total
includes taxes & fees
Nov 5 - Nov 6
4thedome
Property grounds

18. Moonwood House - Welcome to country living at its very finest.

Moonwood House - Welcome to country living at its very finest.
Beaulieu
9.8 out of 10, Exceptional, (12 reviews)
"Superb accommodation pristine throughout, ideal location for local pubs walks and restaurants, Would recommend for a family get together, the children loved it too"
United States
Anonymous traveller
The price is CA $4,708
CA $4,708 total
includes taxes & fees
Oct 15 - Oct 16
Moonwood House - Welcome to country living at its very finest.
A narrow stream with clear water, surrounded by lush greenery and wildflowers.

19. Roslyn

Roslyn
2.0 star property
Romsey
The price is CA $813
CA $975 total
includes taxes & fees
Oct 19 - Oct 20
Roslyn
A hammock between trees overlooking a beach with boats and a fence.

20. Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR

Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR
Cowes
10.0 out of 10, Exceptional, (27 reviews)
"Great location, lovely cottage and a convenient place to explore Cowes."
United Kingdom
Lisa
The price is CA $229
CA $259 total
includes taxes & fees
Oct 14 - Oct 15
Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR
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.
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Top Winsor Hotel Reviews

Village Hotel Southampton Eastleigh

Village Hotel Southampton Eastleigh

10/10 Excellent
"One of EV chargers not working Sink wouldn’t drain Apart from that nice room great food and service"
Julian 1-night trip
Posted less than an hour ago
Village Hotel Southampton Eastleigh

Find out more about Winsor

Everything you need to know about Winsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winsor vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winsor vacation rentals we have selected for you start as low as CA $146 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 vacation 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 vacation.

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 vacation rentals in Winsor?

Yes, we give you a choice of vacation rentals close to the most popular sights in Winsor, or you can select a more remote option if you're looking for relaxation.

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

Unique waterside home in stunning location.: You might want to consider this vacation home rental near Winsor, which is located on the waterfront and has a balcony, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.