A forested area with a dirt path, tall trees, and dense underbrush.

Search Holiday Rentals in Winsor

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.

Dates

November 2026

December 2026

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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

Gary

includes taxes & fees

13 Nov - 14 Nov

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

2. Southampton Serviced Apartment

Bassett

Emma

includes taxes & fees

9 Dec - 10 Dec

A bedroom with a bed, a chair, a wardrobe, and a radiator.

3. Coventry Road Apartments Flat 1

The Polygon

includes taxes & fees

9 Nov - 10 Nov

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

4. Settle Southampton

Freemantle

Chris

includes taxes & fees

15 Nov - 16 Nov

A red brick building with a white door, numbered 22, and a small garden area with potted plants.

5. 19 Quayside Walk

Southampton

includes taxes & fees

12 Nov - 13 Nov

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

6. QE2 Loft Apartments

Southampton City Centre

kia

includes taxes & fees

9 Nov - 10 Nov

A bedroom with a bed, a TV, and a window with curtains.

7. Bayview Apartments

Southampton City Centre

Donald

includes taxes & fees

15 Nov - 16 Nov

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

8. Settle Winchester

Winchester City Center

includes taxes & fees

17 Nov - 18 Nov

9. Cosy studio flat in the Polygon

The Polygon

"It did not satisfy us at all. We left after 4 hours and did not stay the night as we didn’t feel comfortable to. it was a very tiny place compared to the pictures. The toilet seat was yellow, and there was no evidence of the place being cleaned. It was very dusty and the oven had a dirty pan in there. It looked like food had been cooked on it and not washed. There was no cutlery or anything the microwave seemed broken. The bed was uncomfortable and the pillows very light. The cover felt like...

Aminah

includes taxes & fees

9 Nov - 10 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.

10. Charles Hope Salisbury Centre

Salisbury

Theodros

includes taxes & fees

9 Nov - 10 Nov

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

11. Peartree Serviced Apartments

Salisbury

Stephanie

includes taxes & fees

22 Nov - 23 Nov

A bedroom with a bed, a wooden bench, a staircase, and a wall-mounted light fixture.

12. Pinnacle Suites

Cowes

Simon

includes taxes & fees

26 Nov - 27 Nov

13. The South Coast Snug

Fareham

Nikki

includes taxes & fees

13 Nov - 14 Nov

A modern living room with a grey sofa, a coffee table, and a chandelier.

14. Luxury Flat With Parking & Underfloor Heating

Bournemouth

"A lovely, modern, spacious, flat. Private entrance with a huge driveway to park your car. Spotlessly clean, very comfortable bed, lovely & warm with the underfloor heating. Host left tea, coffee sugar there was also salt, pepper & cleaning items. A great location & short walk to a main high street with lots of shops, bars & restaurants. Quick communication from host, also explaining well how to gain access in to the property. I wouldn't hesitate staying here again."

Steven

includes taxes & fees

2 Dec - 3 Dec

A narrow stream with clear water, surrounded by lush greenery and wildflowers.

15. Roslyn

Romsey

includes taxes & fees

12 Nov - 13 Nov

A modern house with a patio area featuring a sofa, chairs, and a dining table.

16. Pamper House Holiday Home And Annex

Ferndown

includes taxes & fees

9 Nov - 10 Nov

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

17. Beddoe Apartments

Eastleigh

Alan

includes taxes & fees

15 Nov - 16 Nov

A living room with a sofa, a coffee table, and a TV. There is a dining area with a table and chairs in the background.

18. Salisbury Residences by Charles Hope

Salisbury

A pier extending into calm waters with a clear sky above.

19. 2 Bedroom Apartment With Balcony, Double Bed & Single Bed in Living Room

Boscombe

includes taxes & fees

9 Nov - 10 Nov

A beach with boats, a pier, and beach huts.

20. Isle 2-bed Retreat- Sleeps 4, Garden & Games Room

Cowes

includes taxes & fees

9 Dec - 10 Dec

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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

Sharron

A cozy room with a fireplace, a sofa, a dining table with a menu, and a bookshelf.

The Bell Inn

Lyndhurst

10/10 Excellent

paul

A hotel room with a large bed, a TV, a brick accent wall, and artwork on the walls.

The New Forest Inn

Lyndhurst

10/10 Excellent

Nicola

A modern kitchen with white subway tiles, stainless steel appliances, and wooden cabinets.

Holiday Inn Express Southampton - West by IHG

Southampton

10/10 Excellent

Susan

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

Stephen

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

Woodlands Hotel

Southampton

10/10 Excellent

Louise

A round wooden table with a small potted plant, wicker chairs, and a thatched-roof building in the background.

The Pilgrim Inn

Southampton

10/10 Excellent

Sally

A man sitting at a table in a cafe with hanging plants, wooden furniture, and a bar in the background.

The Cromwell Arms

Romsey

10/10 Excellent

Julie

A cozy room with a fireplace, a round wooden table, and a bar area.

The Mortimer Arms

Romsey

10/10 Excellent

Sue

Second Nature Southampton

Southampton City Centre

10/10 Excellent

Jonathan

A restaurant with round tables, chandeliers, and floral centerpieces.

Forest Park Country Hotel & Inn, Brockenhurst, New Forest

Brockenhurst

10/10 Excellent

Lovely spacious comfortable room, very clean and beautifully quiet. Tea and coffee supplies locally sourced where possible as were a lot of items on the menu. We enjoyed dinner and breakfast at the hotel and really enjoyed everything. Bar well stocked with an excellent range. Attentive lovely staff, who know how to be in stealth mode and not interrupt while you’re in full swing of conversation. Alas the weather wasn’t so cheery but it’s a great spot for getting out and about for a walk, and we...

Steven

A marina with boats docked, a modern building with outdoor seating, and a glass-enclosed area.

Harbour Hotel Southampton

Southampton City Centre

10/10 Excellent

Giuseppe

A large estate with a formal garden, a central water feature, and a grand building.

Rhinefield House Hotel

Brockenhurst

10/10 Excellent

Conner

A cozy loft apartment with a dining area, a sofa, a TV, and skylights.

New Forest Lodge

Salisbury

10/10 Excellent

BalletLeanne

The exterior of the Leonardo Hotel with a modern entrance, two potted plants, and a sign indicating it is a hotel.

Leonardo Hotel Southampton

The Polygon

10/10 Excellent

Julie

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 £56 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.

Search 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. Southampton Serviced Apartment

3. Coventry Road Apartments Flat 1

4. Settle Southampton

5. 19 Quayside Walk

6. QE2 Loft Apartments

7. Bayview Apartments

8. Settle Winchester

9. Cosy studio flat in the Polygon

10. Charles Hope Salisbury Centre

11. Peartree Serviced Apartments

12. Pinnacle Suites

13. The South Coast Snug

14. Luxury Flat With Parking & Underfloor Heating

15. Roslyn

16. Pamper House Holiday Home And Annex

17. Beddoe Apartments

18. Salisbury Residences by Charles Hope

19. 2 Bedroom Apartment With Balcony, Double Bed & Single Bed in Living Room

20. Isle 2-bed Retreat- Sleeps 4, Garden & Games Room

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?

Explore a world of travel with Expedia