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Compare 419 Vacation Homes in Winsor with updated reviews, rates, and availability.

The Cliff House

4.0 star property
9.4 out of 10, Exceptional, (359)
"Very friendly , helpful staff. Hotel and our room was very contemporary and extremely clean . Added bonus was a sea view from our room. Would definitely recommend this hotel and will certainly return for another visit."
The price is SAR 584
SAR 685 total
includes taxes & fees
26 Nov - 27 Nov
The Cliff House

Two Bare Feet

3.5 star property
9.4 out of 10, Exceptional, (39)
"Wonderful stay for two nights at Two Bare Feet. I was in Little House. Absolutely lovely space. The bed is on a mezzanine, however comfortable and I was pleased there was a fan I could use to keep me cool on one of the hottest days of the year. The finishing touches in the bathroom all felt luxurious. "
The price is SAR 383
SAR 460 total
includes taxes & fees
26 Nov - 27 Nov
Two Bare Feet

Coastal family holiday home near stunning sandy beaches & River Stour in Dorset.

9.8 out of 10, Exceptional, (10)
"We were here for a family event. The house is perfect for 3 families coming together. Spacious with a kitchen area made for social gatherings. The property is very well equipped with everything you need. Lovely welcome pack to get you started. Beautifully clean, comfortable beds. Home from home. Well appointed for Christchurch and Bournmouth."
Coastal family holiday home near stunning sandy beaches & River Stour in Dorset.

Unique waterside home in stunning location.

9.8 out of 10, Exceptional, (94)
"A really unique location in a converted boathouse right on the waterfront. When not out and about we spent a happy time just sitting watching the tide come in and out with loads of bird-life and passing cruise linsers. Right by Waitrose for emergency shopping and very short walk to restaurants"
Unique waterside home in stunning location.

3 bed bungalow with large garden. discount on selected dates for weekly bookings

9.6 out of 10, Exceptional, (41)
"The bungalow was very comfortable, well furnished and beautifully clean. There was a large garden but sadly the weather was too wet to sit in it, we just had to enjoy it from the comfortable conservatory. The area was a quiet road with several nearby places to eat. Public transport was good. "
3 bed bungalow with large garden. discount on selected dates for weekly bookings

Squirrels Drey

10.0 out of 10, Exceptional, (49)
"Always a perfect stay 🥰"
Squirrels Drey

Beautiful 2-bed Apart in Southampton

3.0 star property
Beautiful 2-bed Apart in Southampton

Remodelled historical cottage, super location, w/hottub

9.6 out of 10, Exceptional, (33)
"We found this a great location for our 3 day cycling tour of the 2 forests (10 cycling with 2 back up cars) We also used Luigi the resident chef on the Saturday night for our GALA dinner."
Remodelled historical cottage, super location, w/hottub

COSY QUIRKY COACH HOUSE, HOT TUB,PARKING, SLEEPS 7, BY THE LAKE, 20mins to Poole

9.6 out of 10, Exceptional, (22)
"My husband and I celebrated our 20 year wedding anniversary with my parents. The Coach House is beautifully decorated! We were lucky with the weather and spent a lot of our evenings in the garden. A previous review mentioned the garden not being secure for their dog. Before booking I checked if this was being rectified as we have 2 Westies. I was assured it would be before the start of the season, and confirm the garden is secure for Westie sized and upwards dogs. As well as Bournemouth...
COSY QUIRKY COACH HOUSE, HOT TUB,PARKING, SLEEPS 7, BY THE LAKE, 20mins to Poole

Beautiful, cosy New Forest 2 bed cottage, close to the beach!

9.4 out of 10, Exceptional, (8)
"We stayed for 8 days and thoroughly enjoyed our stay. The accommodation is great. The accommodation is clean, comfortable and well kitted out. The check in was easy too. We’ve enjoyed being so close to both the New Forest and the sea at Milford. Bournemouth is easily accessible for day trips too."
Beautiful, cosy New Forest 2 bed cottage, close to the beach!

Bournemouth Getaway for 14

9.4 out of 10, Exceptional, (3)
"The house was clean and very functional. it was the perfect house for a group of friends."
Bournemouth Getaway for 14

Special offer 20% discount per night until December 20th 2023

10.0 out of 10, Exceptional, (40)
"We loved the cottage, so much space for the 4 of us, equipped with pretty much everything. We will definitely come back and stay again."
Special offer 20% discount per night until December 20th 2023

Luxury home in the New Forest featuring a year-round heated swimming pool.

10.0 out of 10, Exceptional, (1)
"Six of us stayed here for a weekend, each of us were immensely impressed. Expectations were already high on account of the professional contacts with the property managers beforehand and the quality of the digital literature they provided to prepare us for our stay. But the premises more than met these expectations. The place has real charm and character yet is filled with state-of-the-art gadgetry and impressive inspiration that was user-friendly. We were never confused by anything that...
Luxury home in the New Forest featuring a year-round heated swimming pool.

Luxury Historic House/Wood Burning Stove/Wifi/Parking/Parking/Pet Friendly

10.0 out of 10, Exceptional, (24)
"Everything about The Old Bank House was exceptional. The house is beautifully furnished and equipped to a very high standard. At the same time we were made to feel comfortable and welcome to enjoy the space without any restrictions. The bedrooms were all good sized with very comfy beds. It’s ideally located in the village centre, with easy and convenient parking. And the host, Matthew, was very accommodating and responsive. I can’t recommend this property more highly - book it if you can! "
Luxury Historic House/Wood Burning Stove/Wifi/Parking/Parking/Pet Friendly

Historic Listed Cottage In Beaulieu/ Wifi/ Wood Burning Stove/ Parking

10.0 out of 10, Exceptional, (30)
"The cottage was much bigger than expected, extremely clean yet still very cosy The open planned layout of the kitchen and the dining room overlooking the garden is a fabulous social space. And the sitting room with the log burner is very comfortable and spacious. It's a very lovely cottage in an ideal location ... really quiet at night. We could not have wished for more"
Historic Listed Cottage In Beaulieu/ Wifi/ Wood Burning Stove/ Parking

4-bedroom house in prime location

10.0 out of 10, Exceptional, (2)
"Lovely house, spotlessly clean. Heating was on when we arrived and the Christmas tree was twinkling. The house is spacious and welcoming. The hosts are very helpful. Sky glass tv in the lounge was brilliant Loved the musical theme throughout Would definitely book again We had a great Christmas stay"
4-bedroom house in prime location

Ferndown Holiday Let

3.5 star property
9.6 out of 10, Exceptional, (5)
"Spacious ground apartment fully furnished."
Ferndown Holiday Let

Modern Bungalow, private gated entrance and garden.

10.0 out of 10, Exceptional, (1)
"Accommodation was exactly as advertised , couldn’t fault anything Was so nice being able to let the dogs out without worrying about them getting out Would book to stay here again and would highly recommend"
Modern Bungalow, private gated entrance and garden.

Beautiful Tranquil Barn in 14 acres of perfect peace within New Forest district

10.0 out of 10, Exceptional, (3)
"We have just spent 2 nights at the barn. The rooms are extremely spacious and there was plenty of room for the 6 of us which included 4 adults and two children. One bedroom had an en-suite bathroom with fabulous shower and the other two bedrooms shared a bathroom. The kitchen was well stocked with everything you need and if you want to use the bbq it’s right outside the door. We went to the Italian restaurant in town which I can recommend. There are a couple of bakers, a butchers plus a...
Beautiful Tranquil Barn in 14 acres of perfect peace within New Forest district

Charming rural property with a nautical feel.

9.8 out of 10, Exceptional, (10)
"We enjoyed our stay at this characterful secluded property. The large dining room table was ideal for our family, as was the privacy of the location."
Charming rural property with a nautical feel.
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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Other property types in Winsor

Lovely cottage & garden. 5 min drive from Paultons Park, home of Peppa Pig

9.4 out of 10, Exceptional, (115)
"My friends and I had a wonderful stay here. Beautiful garden, clean and comfortable interior, great spaces for socializing and cooking. Well equipped! Ample parking. Great position for exploring. Would love to come back again with my children as it has everything you need for little ones too. Thanks for a lovely stay."
Lovely cottage & garden. 5 min drive from Paultons Park, home of Peppa Pig

room2 Southampton Hometel

4.0 star property
9.4 out of 10, Exceptional, (900)
"Wonderful room .A little cold in the room when we arrived. Pillows a little bit hard . Bed comfy . Everything was well thought out x"
The price is SAR 310
SAR 360 total
includes taxes & fees
28 Nov - 29 Nov
room2 Southampton Hometel

Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!

9.8 out of 10, Exceptional, (178)
"A great holiday was had by all. The property is fantastic, as were out hosts. Timo was great in sorting out any issues we had during our stay"
Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!
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.