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
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Winsor vacation rentals

Exterior

The South Coast Snug

The South Coast Snug
2.0 star property
Fareham
10.0 out of 10, Exceptional, (1 review)
"Lovely appartment.very welcoming, clean and tidy, all equipment was their to use for a pleasant stay.very quiet.would highly reccomend"
United Kingdom
Ian
The price is AED 230
AED 276 total
includes taxes & fees
16 Jun - 17 Jun
The South Coast Snug
Deluxe Studio | Iron/ironing board, free WiFi

Settle Southampton

Settle Southampton
2.0 star property
Freemantle
10.0 out of 10, Exceptional, (3 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is AED 247
AED 518 total
includes taxes & fees
17 Jun - 18 Jun
Settle Southampton
Double Room | Iron/ironing board, free WiFi

Settle Winchester

Settle Winchester
2.0 star property
Winchester
The price is AED 182
AED 708 total
includes taxes & fees
7 Jun - 8 Jun
Settle Winchester
Interior entrance

room2 Southampton Hometel

room2 Southampton Hometel
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,225 reviews)
"All services have been great for our 2 evening stay "
Canada
shawn
The price is AED 384
AED 461 total
includes taxes & fees
21 Jun - 22 Jun
room2 Southampton Hometel
Deluxe Apartment | Living area | Flat-screen TV

Charles Hope Salisbury Centre

Charles Hope Salisbury Centre
3.5 star property
Salisbury
9.6 out of 10, Exceptional, (8 reviews)
"Clean modern room, well equipped and great locaton"
United Kingdom
Theodros
The price is AED 405
AED 486 total
includes taxes & fees
3 Jun - 4 Jun
Charles Hope Salisbury Centre
Exterior

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 810
AED 810 total
includes taxes & fees
5 Jun - 6 Jun
1 bedroom accommodation in Burgate, near Fordingbridge
Deluxe Suite | Premium bedding, Select Comfort beds, desk, laptop workspace

Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.4 out of 10, Exceptional, (30 reviews)
"Good location. Only 2 minutes walk from ferry terminal"
United Kingdom
harold
The price is AED 678
AED 814 total
includes taxes & fees
9 Jun - 10 Jun
Pinnacle Suites
Property grounds

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, (23 reviews)
"Awesome place to stay- we absolutely loved it and will be back"
United Kingdom
Edward
The price is AED 707
AED 811 total
includes taxes & fees
8 Jun - 9 Jun
Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR
Hair dryer, towels, soap, shampoo

Beautiful 2 bedroom full-furnished semi-detached house with parking

Beautiful 2 bedroom full-furnished semi-detached house with parking
Dibden Purlieu
9.6 out of 10, Exceptional, (7 reviews)
"Accommodation was beautifully clean and well equipped in a great location. "
United Kingdom
Julie P.
The price is AED 623
AED 707 total
includes taxes & fees
3 Jun - 4 Jun
Beautiful 2 bedroom full-furnished semi-detached house with parking
Living area

Cape 12,

Cape 12,
2.0 star property
Yarmouth
The price is AED 1,475
AED 1,770 total
includes taxes & fees
13 Jun - 14 Jun
Cape 12,
Terrace/patio

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

Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Winchester
9.0 out of 10, Wonderful, (4 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 712
AED 954 total
includes taxes & fees
4 Jun - 5 Jun
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Exterior

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, (13 reviews)
"Lovely 1 night stay in beautiful location. Louise very welcoming and property was perfect and very clean."
United Kingdom
Emily S.
The price is AED 868
AED 991 total
includes taxes & fees
14 Jun - 15 Jun
Farm Cottage on a Secluded 9-acre Equestrian Small Holding
Interior

Quirky Railway Carriages

Quirky Railway Carriages
Hinton
10.0 out of 10, Exceptional, (3 reviews)
"We booked a last minute short break with our dog Bear. The Railway Carriages was a lovely quirky place with a fabulous big fully enclosed garden which Bear loved. It was lovely and clean with comfy beds. Great location for New Forest and local beaches. We will definitely come again."
United States
Sally
Quirky Railway Carriages
Terrace/patio

Luxury shepherd's hut

Luxury shepherd's hut
Bransgore
9.8 out of 10, Exceptional, (43 reviews)
"The hut was in great condition, with luxurious amenities and amazing views of the countryside. It made for a very peaceful and welcoming stay!"
United States
Paul A.
The price is AED 752
AED 861 total
includes taxes & fees
7 Jun - 8 Jun
Luxury shepherd's hut
Exterior

Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.

Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.
Stockbridge
9.6 out of 10, Exceptional, (103 reviews)
"Pretty and comfortable cottage - was lovely and warm. Lovely touch to have a Christmas tree and lights. We all thoroughly enjoyed our stay. "
United Kingdom
Karen D.
The price is AED 865
AED 984 total
includes taxes & fees
4 Jun - 5 Jun
Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.
Shower

West Sea View No 5 , Yarmouth

West Sea View No 5 , Yarmouth
Yarmouth
The price is AED 1,765
AED 1,765 total
includes taxes & fees
5 Jun - 6 Jun
West Sea View No 5 , Yarmouth
Shower

Squirrels Drey, Titchfield Common

Squirrels Drey, Titchfield Common
Fareham
The price is AED 3,784
AED 3,784 total
includes taxes & fees
5 Jun - 6 Jun
Squirrels Drey, Titchfield Common
Miscellaneous

Beddoe Apartments

Beddoe Apartments
3.0 star property
Eastleigh
8.2 out of 10, Very Good, (19 reviews)
"Ideal for couple of nights stay. Easy parking was a bonus. "
United Kingdom
Alan
The price is AED 577
AED 915 total
includes taxes & fees
5 Jun - 6 Jun
Beddoe Apartments
Outdoor dining

Cape A1,Yarmouth,Isle of Wight

Cape A1,Yarmouth,Isle of Wight
Yarmouth
10.0 out of 10, Exceptional, (1 review)
"The property was clean, pleasantly decorated and contained all the essentials we needed for a small family group. It was good to have a table and chairs on the decked area overlooking grassed space, where my grandson could play. Good location, near Fort Victoria and Colwell Bay and a short drive from the shops in Freshwater."
United States
Melanie S.
The price is AED 2,087
AED 2,087 total
includes taxes & fees
8 Jun - 9 Jun
Cape A1,Yarmouth,Isle of Wight
Interior

Little Timbers

Little Timbers
3.0 star property
Ringwood
The price is AED 1,182
AED 1,419 total
includes taxes & fees
28 Jun - 29 Jun
Little Timbers
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

voco Southampton by IHG

voco Southampton by IHG

4/10 Poor
"20 pounds to park ..absolute joke"
paul 1-night trip
Posted 1 hour ago
voco Southampton by IHG

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.: Visitors like this Winsor vacation home rental. It 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.