Winsor Holiday Rentals from €92: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Winsor has to offer?

Unique waterside home in stunning location. : This holiday home rental outside of Winsor 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 that you can cook with friends or family.

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Our top choices for Winsor holiday rentals

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

1. Second Nature Southampton

Southampton City Centre

Yahong Susan

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a large bed, a wooden ceiling, and a view of a brick building outside.

2. Settle Southampton

Freemantle

Chris

includes taxes & fees

15 Nov - 16 Nov

An outdoor patio with a brick wall, a grill, wicker furniture, and a dining table.

3. Beautiful New Forest Hideaway

West Wellow

Alena M.

includes taxes & fees

15 Nov - 16 Nov

A hotel room with a bed, a large mirror, a painting on the wall, and a view of another room.

4. 216a Bassett Green Rd

Bassett Green

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a radiator.

5. Settle Winchester

Winchester City Center

includes taxes & fees

19 Nov - 20 Nov

A bedroom with a large bed, a nightstand, a wall-mounted lamp, and a window with blinds.

6. Southampton Serviced Apartment

Bassett

Emma

includes taxes & fees

15 Nov - 16 Nov

A row of wooden cabins with attached porches, each with a small porch light.

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

Salisbury

Diana T.

includes taxes & fees

19 Nov - 20 Nov

An outdoor patio with wooden furniture, a table set for dining, and a pergola with climbing plants.

8. New Forest National Park Studio @Forest Palms

Hyde

Dan R.

includes taxes & fees

1 Dec - 2 Dec

A kitchen counter with vegetables, a sink, and potted plants.

9. Beddoe Apartments

Eastleigh

Alan

includes taxes & fees

15 Nov - 16 Nov

A calm waterfront with a boat docked, a swan, and ducks swimming. There is a round table and a chair in the foreground.

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

Portswood

Terri M.

includes taxes & fees

19 Nov - 20 Nov

A modern kitchen with a central island, bar stools, hanging plants, and a variety of appliances.

11. Adorable 2-bedroom apartment in Southampton

Freemantle

Bethany M.

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a large bed, a sofa, a TV, and a window with blinds.

12. QE2 Loft Apartments

Southampton City Centre

kia

includes taxes & fees

16 Nov - 17 Nov

A sign for Hotel Peartree, a serviced apartment, with contact information and website.

13. Peartree Serviced Apartments

Salisbury

Stephanie

includes taxes & fees

15 Nov - 16 Nov

A traditional thatched-roof cottage with a brick extension, a white door, and a small window.

14. 1 bedroom accommodation in Burgate, near Fordingbridge

Burgate, near Fordingbridge

Angela Horn

includes taxes & fees

30 Nov - 1 Dec

A bedroom with a wooden door, a bed with a beige and white striped bedspread, a fluffy beige throw blanket, and a pink pillow. There are framed pictures on the wall and a window with curtains.

15. The Bike Shed

Romsey

includes taxes & fees

23 Nov - 24 Nov

A living room with a dark blue sofa, a round wooden coffee table, a dining table with chairs, a large abstract painting, a round mirror, and a window with curtains.

16. Charles Hope Salisbury Centre

Salisbury

Theodros

includes taxes & fees

26 Nov - 27 Nov

A wooden cabin with an open door revealing a kitchen area, two wicker chairs, and a small wooden table.

17. Luxurious shepherd's chalet

Bransgore

Hayley M.

includes taxes & fees

15 Nov - 16 Nov

A coastal beach with a rocky cliff and a clear view of the sea.

18. Unique detached holiday cottage, Hampshire

Sopley

Keiron D.

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with a built-in island, a sink, and a clock on the wall.

19. 4thedome

New Milton

"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"

Ceri

includes taxes & fees

22 Nov - 23 Nov

A wooden cabin with a sloped roof, a deck with two chairs, and a glass door leading inside.

20. Cosy A-Frame cabin nestled in the chalk steams of Hampshire

Winchester

Nicola H.

includes taxes & fees

15 Nov - 16 Nov

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Find holiday rentals that suit your style

Top Winsor Hotel Reviews

A grand staircase with a large elk sculpture, a chandelier, and a cozy seating area with a fireplace.

The Crown Manor House Hotel

Lyndhurst

10/10 Excellent

Ed

A large house with a conservatory, a garden with various plants, and a chimney.

Woodlands Hotel

Southampton

8/10 Good

Anonymous traveller

A cozy room with a wooden bench, a sofa, and a table with a glass display case.

The White Horse Hotel, Romsey, Hampshire

Romsey

10/10 Excellent

KATHRYN

A modern, compact mobile home with a sliding door, a small patio with a table and chairs, and a wooden fence.

High Corner Inn

Ringwood

8/10 Good

Anonymous traveller

A brick building with a sign for 'The White Star' dining, bar, and rooms.

The White Star Tavern

Southampton City Centre

10/10 Excellent

Clive

Find out more about Winsor

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 €92 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 close to the most popular sights in Winsor, or you can select a more secluded option if you're looking for a relaxing stay.

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

Unique waterside home in stunning location.: This holiday home rental outside of Winsor 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 that 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 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.

Holiday Rentals in Winsor

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winsor holiday rentals

1. Second Nature Southampton

2. Settle Southampton

3. Beautiful New Forest Hideaway

4. 216a Bassett Green Rd

5. Settle Winchester

6. Southampton Serviced Apartment

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

8. New Forest National Park Studio @Forest Palms

9. Beddoe Apartments

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

11. Adorable 2-bedroom apartment in Southampton

12. QE2 Loft Apartments

13. Peartree Serviced Apartments

14. 1 bedroom accommodation in Burgate, near Fordingbridge

15. The Bike Shed

16. Charles Hope Salisbury Centre

17. Luxurious shepherd's chalet

18. Unique detached holiday cottage, Hampshire

19. 4thedome

20. Cosy A-Frame cabin nestled in the chalk steams of Hampshire

Find holiday rentals that suit your style

Top Winsor Hotel Reviews

The Crown Manor House Hotel

10/10 Excellent

Find out more about Winsor

Winsor holiday rentals: An excellent choice for every season

How to find incredible deals on Winsor rentals

Frequently Asked Questions

Are there holiday rentals in Winsor?

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

What can I see and do in Winsor?

What are holiday rentals like in Winsor?