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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 484 Vacation Homes in Winsor with updated reviews, rates, and availability.

The Cliff House Hotel
Exterior

The Cliff House Hotel

4.0 star property
9.4 out of 10, Exceptional, (376)
"Everything about the property was incredible. The welcome from Jordan and just the way it felt like home from home "
The price is AED 673
AED 808 total
includes taxes & fees
30 Mar - 31 Mar
The Cliff House Hotel
7 bedroom, Stunning Cottage with Hot-Tub & Cinema Room - opens 15.4.25
Outdoor dining

7 bedroom, Stunning Cottage with Hot-Tub & Cinema Room - opens 15.4.25

9.8 out of 10, Exceptional, (135)
"We had a lovely stay, property unique and in perfect new forest setting. We will be back!"
7 bedroom, Stunning Cottage with Hot-Tub & Cinema Room - opens 15.4.25
5-bed house: pool, tennis court, walk to beach, 10 acres
Exterior

5-bed house: pool, tennis court, walk to beach, 10 acres

10.0 out of 10, Exceptional, (59)
"We spent 5 excellent days over Christmas, creating some wonderful memories. This was the second time we stayed here, with the added excitement of families together at Xmas. The house is large so plenty of space for everyone. All beds very comfortable Extensive gardens, and all kinds of outdoor games and outdoor equipment for all ages. Take your microwave as this helps a lot to supplement AGA cooking if you’re not used to cooking on one!"
5-bed house: pool, tennis court, walk to beach, 10 acres
Cathedral view, stunning 3 bedroom townhouse
Fridge, microwave, oven, stovetop

Cathedral view, stunning 3 bedroom townhouse

9.6 out of 10, Exceptional, (29)
"This is a very nice house that is extremely well placed for the Cathedral Close. It is on a busy road but generally one doesn't notice the traffic once inside the house."
Cathedral view, stunning 3 bedroom townhouse
10 Westgate Street - 5 Star 18th Century House
Outdoor dining

10 Westgate Street - 5 Star 18th Century House

10.0 out of 10, Exceptional, (11)
"What a great property. Its location to restaurants, historical sites, and the cruise terminal was fantastic. The house felt very homey and comfortable. If I return to Southampton I will definitely look to stay here again. "
10 Westgate Street - 5 Star 18th Century House
Remodelled historical cottage, super location, w/hottub
Outdoor spa tub

Remodelled historical cottage, super location, w/hottub

9.6 out of 10, Exceptional, (36)
"We had a great stay for new years, Timo looked after us well"
Remodelled historical cottage, super location, w/hottub
Unique waterside home in stunning location.
Interior

Unique waterside home in stunning location.

9.8 out of 10, Exceptional, (96)
"Perfect location for a short break just sitting and watching everything going by on the water"
Unique waterside home in stunning location.
Chatsworth House by NewFo.rest
Miscellaneous

Chatsworth House by NewFo.rest

Chatsworth House by NewFo.rest
Stylish Georgian Town House in the heart of Salisbury
Smart TV, fireplace, DVD player, books

Stylish Georgian Town House in the heart of Salisbury

10.0 out of 10, Exceptional, (62)
"The house is situated on three different levels. There is a beautiful open kitchen with dining room and lounge downstairs. The kitchen is fully equipped with everything you will need from serving a bowl of cereal. tohaving a cocktail. "
Stylish Georgian Town House in the heart of Salisbury
Eighty-Eight, Cathedral View with Private Parking & EV Charger
Fridge, microwave, oven, stovetop

Eighty-Eight, Cathedral View with Private Parking & EV Charger

9.6 out of 10, Exceptional, (8)
"This is a very nice clean and light house. Jim and Laura were extremely helpful hosts. It was also an added bonus that there is free parking at the back of the house."
Eighty-Eight, Cathedral View with Private Parking & EV Charger
Squirrels Drey
Interior

Squirrels Drey

10.0 out of 10, Exceptional, (49)
"Always a perfect stay 🥰"
Squirrels Drey
Beautiful 2-bed Apart in Southampton
House, 2 Queen Beds | 2 bedrooms, iron/ironing board, free WiFi, bed sheets

Beautiful 2-bed Apart in Southampton

3.0 star property
Beautiful 2-bed Apart in Southampton
The Lodge By The Lake at Shorefield Holiday Park
Exterior

The Lodge By The Lake at Shorefield Holiday Park

9.8 out of 10, Exceptional, (107)
"Loved our stay at the lodge really comfy everything you needed.Especially loved the walks through the forest to the sea. My other half enjoyed the fishing I would definitely recommend "
The Lodge By The Lake at Shorefield Holiday Park
New Forest house with large garden, near sea. Perfect for families with children
Beach nearby

New Forest house with large garden, near sea. Perfect for families with children

9.0 out of 10, Wonderful, (55)
"We had a family weekend in the New Forest. This was a lovely property with a gorgeous outdoor space in a fab location. The hosta were incredibly helpful and we're very communicative. We enjoyed out stay and I was surprised withe the amenities and everything there was there. We would definitely recommend this property and the hosts."
New Forest house with large garden, near sea. Perfect for families with children
Bournemouth Getaway for 14
Fridge, microwave, oven, stovetop

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
Luxury shepherd's hut
Terrace/patio

Luxury shepherd's hut

10.0 out of 10, Exceptional, (35)
"We stay one night and it was such a beautiful and cozy hut. We really loved it "
The price is AED 568
AED 653 total
includes taxes & fees
31 Mar - 1 Apr
Luxury shepherd's hut
Elmside, The New Forest Retreat
Outdoor spa tub

Elmside, The New Forest Retreat

10.0 out of 10, Exceptional, (1)
"This is a lovely, huge comfortable property with plenty of room for a large family to spread out - it is actually bigger than it appears in the photos. It has been stylishly decorated and fitted out in a contemporary style, but still feels like a home from home. The road is very quiet, and it feels like you're in a peaceful, rural location. You are very close to both the forest and the sea with lots to do nearby. It is very secure for children - once the gates are closed they can play in the...
Elmside, The New Forest Retreat
3 bed bungalow with large garden. discount on selected dates for weekly bookings
Beach nearby

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

9.6 out of 10, Exceptional, (43)
"Great house comfortable and perfect for a young family all on one level. Space for car and safe area for walking riding bikes. Lovely looking garden although too wet for us to get out so we viewed from the amazing conservatory area. Thanks"
3 bed bungalow with large garden. discount on selected dates for weekly bookings
Perfect crew-house or for business trips. Sleeps 10, 5mins from Hamble Village
Fridge, oven, stovetop, dishwasher

Perfect crew-house or for business trips. Sleeps 10, 5mins from Hamble Village

10.0 out of 10, Exceptional, (1)
"Really good "
Perfect crew-house or for business trips. Sleeps 10, 5mins from Hamble Village
Holiday home hot tub and sauna
Beach

Holiday home hot tub and sauna

9.6 out of 10, Exceptional, (4)
"We had a brilliant time over Christmas 2023. The home was very clean and comfortable with everything we needed. Would love to stay again. Great location too."
The price is AED 780
AED 1,632 total
includes taxes & fees
30 Mar - 31 Mar
Holiday home hot tub and sauna
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
Outdoor dining

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
Front of property

room2 Southampton Hometel

4.0 star property
9.6 out of 10, Exceptional, (952)
"The hotel and staff were excellent. Especially Grace who was amazing. The hotel felt like it was run by friends and family. The room was cosy and really homely. We will definitely be returning soon."
The price is AED 298
AED 358 total
includes taxes & fees
30 Mar - 31 Mar
room2 Southampton Hometel
The Cliff House Hotel
Exterior

The Cliff House Hotel

4.0 star property
9.4 out of 10, Exceptional, (376)
"Everything about the property was incredible. The welcome from Jordan and just the way it felt like home from home "
The price is AED 673
AED 808 total
includes taxes & fees
30 Mar - 31 Mar
The Cliff House Hotel
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.