Lodging Image

Winsor Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winsor vacation rentals

A bar area with stools, a counter with various items, and a patterned floor.

1. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,369 reviews)
"Nice staff, clean property. Close to restaurants. Nice park in front of the property. Overall very pleasant stay."
United States
Yahong Susan
The price is AED 312
AED 374 total
includes taxes & fees
15 Nov - 16 Nov
Second Nature Southampton
A room with a bed, a chair, a table, and a window with curtains.

2. Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.2 out of 10, Very good, (14 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is AED 190
AED 446 total
includes taxes & fees
15 Nov - 16 Nov
Settle Southampton
An aerial view of a property with a tennis court, a hot tub, outdoor seating, and a small building.

3. 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 AED 605
AED 848 total
includes taxes & fees
26 Nov - 27 Nov
Beautiful New Forest Hideaway
A bedroom with a bed, a window, a radiator, and a wall with vertical lines.

4. 216a Bassett Green Rd

216a Bassett Green Rd
Bassett Green
The price is AED 437
AED 1,009 total
includes taxes & fees
28 Nov - 29 Nov
216a Bassett Green Rd
A bedroom with a bed, a bedside table, a window, and a view of the outside.

5. Settle Winchester

Settle Winchester
2.0 star property
Winchester City Center
The price is AED 180
AED 479 total
includes taxes & fees
19 Nov - 20 Nov
Settle Winchester
A balcony with wicker chairs, a table with a fruit basket and wine glasses, and a view of houses and trees.

6. Southampton Serviced Apartment

Southampton Serviced Apartment
4.0 star property
Bassett
8.6 out of 10, Excellent, (188 reviews)
"Clean rooms, spacious enough for two for a weekend/long weekend. Easy access to Southampton City centre on the No1 bus, which runs right past the front door. Plenty of parking front and rear to service all the apartments."
United Kingdom
Emma
The price is AED 728
AED 874 total
includes taxes & fees
15 Nov - 16 Nov
Southampton Serviced Apartment
A well-maintained garden with a stone fountain, a wooden house with a stone wall, and a neatly trimmed hedge.

7. 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, (18 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 AED 664
AED 722 total
includes taxes & fees
15 Nov - 16 Nov
Farm Cottage on a Secluded 9-acre Equestrian Small Holding
A wooden deck with a barbecue grill, outdoor furniture, and a large umbrella.

8. 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 AED 558
AED 728 total
includes taxes & fees
1 Dec - 2 Dec
New Forest National Park Studio @Forest Palms
A traditional pub named "The Duke of Wellington" with a white facade, timber framing, and hanging flower baskets.

9. Beddoe Apartments

Beddoe Apartments
3.0 star property
Eastleigh
7.8 out of 10, Good, (20 reviews)
"Ideal for couple of nights stay. Easy parking was a bonus. "
United Kingdom
Alan
The price is AED 607
AED 948 total
includes taxes & fees
15 Nov - 16 Nov
Beddoe Apartments
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

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 AED 656
AED 768 total
includes taxes & fees
15 Nov - 16 Nov
Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton
A modern living room with a grey sofa, a round grey chair, and a small table. There are hanging plants and a radiator in the background.

11. Adorable 2-bedroom apartment in Southampton

Adorable 2-bedroom apartment in Southampton
Freemantle
9.2 out of 10, Wonderful, (5 reviews)
"Apartment was in great condition, no complaints!"
United Kingdom
Bethany M.
The price is AED 691
AED 856 total
includes taxes & fees
15 Nov - 16 Nov
Adorable 2-bedroom apartment in Southampton
A modern bedroom with a large bed, a TV mounted on the wall, a small table with a lamp, and a window with blinds.

12. QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
5.8 out of 10, (18 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 AED 668
AED 802 total
includes taxes & fees
28 Nov - 29 Nov
QE2 Loft Apartments
A modern bathroom with a green wall, a white sink, and a grey sofa.

13. Peartree Serviced Apartments

Peartree Serviced Apartments
3.5 star property
Salisbury
9.6 out of 10, Exceptional, (330 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 AED 404
AED 484 total
includes taxes & fees
15 Nov - 16 Nov
Peartree Serviced Apartments
A traditional thatched-roof cottage with a brick extension, a white door, and a small window.

14. 1 bedroom accommodation in Burgate, near Fordingbridge

1 bedroom accommodation in Burgate, near Fordingbridge
Burgate, near Fordingbridge
10.0 out of 10, Exceptional, (11 reviews)
"Perfect for a weekend away."
United States
Angela Horn
The price is AED 670
AED 670 total
includes taxes & fees
30 Nov - 1 Dec
1 bedroom accommodation in Burgate, near Fordingbridge
A wooden fence with signs for 'Horseshoe Cottage' and 'The Bike Shed'.

15. The Bike Shed

The Bike Shed
3.0 star property
Romsey
The price is AED 1,821
AED 2,185 total
includes taxes & fees
24 Nov - 25 Nov
The Bike Shed
A modern living room with a sofa, a dining table with chairs, a potted plant, and a painting on the wall.

16. Charles Hope Salisbury Centre

Charles Hope Salisbury Centre
4.0 star property
Salisbury
9.4 out of 10, Exceptional, (10 reviews)
"Clean modern room, well equipped and great locaton"
United Kingdom
Theodros
The price is AED 394
AED 594 total
includes taxes & fees
25 Nov - 26 Nov
Charles Hope Salisbury Centre
A wooden cabin with an open door revealing a kitchen area, two wicker chairs, and a small wooden table.

17. Luxurious shepherd's chalet

Luxurious shepherd's chalet
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 AED 739
AED 797 total
includes taxes & fees
15 Nov - 16 Nov
Luxurious shepherd's chalet
A coastal beach with a rocky cliff and a clear view of the sea.

18. 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 AED 424
AED 648 total
includes taxes & fees
16 Nov - 17 Nov
Unique detached holiday cottage, Hampshire
A street with a roundabout, a stone monument, and residential buildings with pitched roofs.

19. 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 AED 404
AED 655 total
includes taxes & fees
22 Nov - 23 Nov
4thedome
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

Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Winchester
8.8 out of 10, Excellent, (8 reviews)
"Lovely cabin and outside kitchen plus garden. It's my second stay and I enjoyed my stay. Love the garden kitchen,. It's very pretty and relaxing ."
United Kingdom
Nicola H.
The price is AED 549
AED 724 total
includes taxes & fees
15 Nov - 16 Nov
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winsor Hotel Reviews

ibis budget Southampton Centre

ibis budget Southampton Centre

10/10 Excellent
"Very convenient location for easy walk to the train station and centre of town. Room was clean and functional and the continental breakfast well stocked."
Gary 3-night trip
Posted 9 hours ago
ibis budget Southampton Centre

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.