Search Vacation Homes in Winchester

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winchester vacation homes

Birdsong House

Birdsong House
Winchester
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at Birdsong house. The owner was always available and the house was so cozy and comfortable! Thank you"
United Kingdom
Judith D.
The price is AED 3,936
AED 4,006 total
includes taxes & fees
17 Feb - 18 Feb
Birdsong House

Birdsong Mansion sleeps 12 Twyford Winchester

Birdsong Mansion sleeps 12 Twyford Winchester
Winchester
The price is AED 4,999
AED 5,069 total
includes taxes & fees
17 Feb - 18 Feb
Birdsong Mansion sleeps 12 Twyford Winchester

Piping House 4bedroom

Piping House 4bedroom
Colden Common
The price is AED 1,339
AED 1,434 total
includes taxes & fees
17 Feb - 18 Feb
Piping House 4bedroom

Piping Green 4Bedroom House

Piping Green 4Bedroom House
Colden Common
The price is AED 1,429
AED 1,524 total
includes taxes & fees
17 Feb - 18 Feb
Piping Green 4Bedroom House

Bury Villa - sleeping 18 guests

Bury Villa - sleeping 18 guests
Gosport
9.6 out of 10, Exceptional, (19 reviews)
"Property was exactly how it was listed. Great location, short walk to the ferry to get over to Portsmouth & short drive to the closest beach. "
United Kingdom
Zoe C.
The price is AED 5,636
AED 5,636 total
includes taxes & fees
23 Feb - 24 Feb
Bury Villa - sleeping 18 guests

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

Beautiful 2 bedroom full-furnished semi-detached house with parking
Dibden Purlieu
9.4 out of 10, Exceptional, (6 reviews)
"Great location, xxx"
United Kingdom
Christopher K.
The price is AED 702
AED 802 total
includes taxes & fees
11 Mar - 12 Mar
Beautiful 2 bedroom full-furnished semi-detached house with parking

The Enchanting Silver Birch Retreat, New Forest

The Enchanting Silver Birch Retreat, New Forest
Southampton
10.0 out of 10, Exceptional, (1 review)
"Exceptional new renovation. Spectacular kitchen facilities and provisions. Great location for access to The New Forest. Wish we were staying here longer. One of the best properties of our trip. "
Canada
Gail V.
The Enchanting Silver Birch Retreat, New Forest

The Pig Sty * WOW Factor Countryside Retreat

The Pig Sty * WOW Factor Countryside Retreat
West Sussex
7.0 out of 10, Good, (2 reviews)
"Cottage was lovely and quirky comfortable and warm, but there was a few issues, cobwebs in the bedroom table lamp in the lounge gave me an electric shock! Stairs outside need looking at as very worn out and not enough utensils pizza tray didn’t fit the small oven. The local Woodmancote pub was great for Sunday lunch and you get a 20% discount too."
United Kingdom
Lindsay
The price is AED 819
AED 1,215 total
includes taxes & fees
18 Feb - 19 Feb
The Pig Sty * WOW Factor Countryside Retreat

Iris home in Southsea, Portsmouth. 15 minute walk to the seafront!

Iris home in Southsea, Portsmouth. 15 minute walk to the seafront!
Southsea
9.6 out of 10, Exceptional, (5 reviews)
"Excellent stay in a nice area. Property was clean, well appointed and ideal for our stay."
United Kingdom
Robert B.
The price is AED 802
AED 973 total
includes taxes & fees
22 Feb - 23 Feb
Iris home in Southsea, Portsmouth. 15 minute walk to the seafront!

Dairy House - a house that sleeps 16 guests in 7 bedrooms

Dairy House - a house that sleeps 16 guests in 7 bedrooms
Gosport
9.8 out of 10, Exceptional, (30 reviews)
"Lovely well eqipped accommodation which was ideal for our family of 14. Rooms were spacious and there was lots to do including a games room. Good location right near the sea."
United Kingdom
Diane S.
The price is AED 6,829
AED 6,829 total
includes taxes & fees
16 Mar - 17 Mar
Dairy House - a house that sleeps 16 guests in 7 bedrooms

Self contained large annexe near Stonehenge

Self contained large annexe near Stonehenge
Figheldean
10.0 out of 10, Exceptional, (1 review)
The price is AED 2,031
AED 2,307 total
includes taxes & fees
22 Feb - 23 Feb
Self contained large annexe near Stonehenge

The Cow Shed * WOW Factor Countryside Retreat

The Cow Shed * WOW Factor Countryside Retreat
West Sussex
4.0 out of 10, (1 review)
"We were excited for our stay as working mums some precious time for R&R was much anticipated. The listing on Arbo looked great … nice setting & a hot tub over looking fields was the tranquil getaway we had in mind. However When we arrived we found the hot tun had not been cleaned (like & mud & hair). Also the temperature was.not hot.The accommodation wa dirty.. cups that were dirty with lisp it marked, shower not cleaned properly & bin dirty too. Worktops also dirty. The response to get it all...
United Kingdom
Harvinder P.
The price is AED 1,096
AED 1,522 total
includes taxes & fees
17 Feb - 18 Feb
The Cow Shed * WOW Factor Countryside Retreat

Little Lane is a charming, recently refurbished 2 bedroom cottage sleeping 4

Little Lane is a charming, recently refurbished 2 bedroom cottage sleeping 4
Gosport
9.8 out of 10, Exceptional, (6 reviews)
"Enjoyable time in Alverstoke. Great place for a mix of excursions and holiday fun."
Germany
Nadine V.
The price is AED 1,999
AED 1,999 total
includes taxes & fees
23 Feb - 24 Feb
Little Lane is a charming, recently refurbished 2 bedroom cottage sleeping 4

modern Bungalow with hot tub, garden, bbq & Netflix 10 min drive to city centre

modern Bungalow with hot tub, garden, bbq & Netflix 10 min drive to city centre
Southampton
10.0 out of 10, Exceptional, (3 reviews)
"The accommodation was very comfortable and perfectly situated for a pre cruise stay! The beds were comfortable and the kitchen was very well equipped! Comfy sofas in the lounge and great internet! Highly recommended! Would definitely book again! Great host too! "
United Kingdom
Michael H.
The price is AED 632
AED 1,028 total
includes taxes & fees
17 Feb - 18 Feb
modern Bungalow with hot tub, garden, bbq & Netflix 10 min drive to city centre

spacious home with pool table, 3 bedrooms, 2 minutes drive from seafront

spacious home with pool table, 3 bedrooms, 2 minutes drive from seafront
Gosport
spacious home with pool table, 3 bedrooms, 2 minutes drive from seafront

Private Garden Annexe + Parking. Near QA Hospital

Private Garden Annexe + Parking. Near QA Hospital
Cosham
The price is AED 375
AED 375 total
includes taxes & fees
19 Feb - 20 Feb
Private Garden Annexe + Parking. Near QA Hospital

5 bedroom family home close to Gosport ferry to Portsmouth and the New Forrest

5 bedroom family home close to Gosport ferry to Portsmouth and the New Forrest
Gosport
The price is AED 477
AED 833 total
includes taxes & fees
10 Mar - 11 Mar
5 bedroom family home close to Gosport ferry to Portsmouth and the New Forrest

Saxon Corner Emsworth 3bed BRAND NEW HOUSE

Saxon Corner Emsworth 3bed BRAND NEW HOUSE
Emsworth
10.0 out of 10, Exceptional, (2 reviews)
"Lovely clean house, with all the amenities supplied that are needed. Comfortable and easy to feel at home."
United Kingdom
Elaine W.
The price is AED 1,088
AED 1,173 total
includes taxes & fees
17 Feb - 18 Feb
Saxon Corner Emsworth 3bed BRAND NEW HOUSE

Fratton House: Alver Road: Free parking

Fratton House: Alver Road: Free parking
Fratton
The price is AED 241
AED 241 total
includes taxes & fees
17 Feb - 18 Feb
Fratton House: Alver Road: Free parking

The Deck House, Isle of Wight

The Deck House, Isle of Wight
Gurnard
The Deck House, Isle of Wight
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.

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews