Holiday Homes in Winchester

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Winchester and around

Two Bare Feet
Flat-screen TV
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 €118
includes taxes & fees
17 Nov - 18 Nov
Two Bare Feet
Lovely dog friendly 2 bed bungalow with parking
Terrace/patio
Lovely dog friendly 2 bed bungalow with parking
9.6 out of 10, Exceptional, (35)
"Perfect place to stay with dogs and children, nice enclosed garden and a toddler safe living room. Well equipped and a great base to explore the new forest. "
Lovely dog friendly 2 bed bungalow with parking
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
Beautiful 2-bed Apart in Southampton
3.0 star property
Beautiful 2-bed Apart in Southampton
Charming 2 bedroom cottage in Lymington, very close to town, marina & sea walks
Exterior detail
Charming 2 bedroom cottage in Lymington, very close to town, marina & sea walks
9.8 out of 10, Exceptional, (114)
"Sea Cottage was just the place my wife and I wanted for a mini-break in the New Forest. A moderate walk from the town centre made it accessible, and car parking was easy. The cottage was clean and with excellent facilities. All our contact with Richard was helpful and friendly. We would be happy to book again. "
Charming 2 bedroom cottage in Lymington, very close to town, marina & sea walks
Unique waterside home in stunning location.
Interior
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.
Spacious semi-detached Southsea House
Outdoor dining
Spacious semi-detached Southsea House
10.0 out of 10, Exceptional, (3)
"We loved this gorgeous home. The decor was beautiful and everything was thoughtfully provided. A perfect house for all 10 of us (a mix of family and friends of all ages) plus we could bring our dog!"
Spacious semi-detached Southsea House
Luxury home in the New Forest featuring a year-round heated swimming pool.
Pool
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.
Rampart View - a house that sleeps 6 guests in 3 bedrooms
Interior
Rampart View - a house that sleeps 6 guests in 3 bedrooms
9.6 out of 10, Exceptional, (5)
"Comfortable. Well equipped. Interesting views. Handy for touring the area. Great restaurant, The Creek very nearby. Bit of a noisy road at night. Lots of stairs. But would stay again"
The price is €832
includes taxes & fees
18 Nov - 19 Nov
Rampart View - a house that sleeps 6 guests in 3 bedrooms
Luxury Historic House/Wood Burning Stove/Wifi/Parking/Parking/Pet Friendly
Third-party on-site parking
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
Large Fun Qwkery four bed house
Pool
Large Fun Qwkery four bed house
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"
Large Fun Qwkery four bed house
6 Pilley Green cottage
Interior
6 Pilley Green cottage
10.0 out of 10, Exceptional, (9)
"We were so happy with this little cottage. It was so cosy and absolutely perfect for a family stay. We had never been to the New Forest before and loved it. We loved waking up to the ponies feeding in the front garden. The little touches like the dog basket with towels and shampoo was much appreciated. We loved it and will definitely be back!"
6 Pilley Green cottage
Little Lane is a charming, recently refurbished 2 bedroom cottage sleeping 4
Terrace/patio
Little Lane is a charming, recently refurbished 2 bedroom cottage sleeping 4
9.6 out of 10, Exceptional, (5)
"Great location in the heart of Alverstoke village, handy for all local attractions."
The price is €718
includes taxes & fees
6 Dec - 7 Dec
Little Lane is a charming, recently refurbished 2 bedroom cottage sleeping 4
Charming rural property with a nautical feel.
Exterior
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.
The Oak Barn conversion with Hot Tub
Interior
The Oak Barn conversion with Hot Tub
8.0 out of 10, Very good, (1)
"The property is in a good location close to a lovely little village with plenty to do in the surrounding area. The hosts were very responsive and helpful."
The Oak Barn conversion with Hot Tub
Spacious home near the Marinas with ample parking
Outdoor dining
Spacious home near the Marinas with ample parking
10.0 out of 10, Exceptional, (1)
"We had a fabulous stay. The house is large and well equipped and the garden is great. Location is excellent. We would definitely return. "
Spacious home near the Marinas with ample parking
Modern city house - close to the city centre
Living area
Modern city house - close to the city centre
The price is €132
includes taxes & fees
15 Dec - 16 Dec
Modern city house - close to the city centre
MANSION WITH SWIMMING POOL, GAMES ROOM, SEA VIEWS, SANDY BEACHES 2 MINS WALK
Beach nearby, sun-loungers
MANSION WITH SWIMMING POOL, GAMES ROOM, SEA VIEWS, SANDY BEACHES 2 MINS WALK
9.8 out of 10, Exceptional, (59)
"There was plenty of space for 13 of us, the rooms were lovely and the games room was a god-send due to the weather!"
MANSION WITH SWIMMING POOL, GAMES ROOM, SEA VIEWS, SANDY BEACHES 2 MINS WALK
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, (53)
"Well situated. Vehicle parking good. Ideal property for large groups. Garden perfect for games. Kitchen/conservatory perfect. Ground floor bathroom could do with some general “Tlc”. Overall our group enjoyed the stay. Would recommend."
New Forest house with large garden, near sea. Perfect for families with children
Cowes retreat
Beach nearby
Cowes retreat
9.2 out of 10, Wonderful, (10)
"Excellent location. Just short walk from red jet. Nice spacious house. Lots of sleep options for group of friends. Good value."
Cowes retreat
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

Two Bare Feet
Flat-screen TV
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 €118
includes taxes & fees
17 Nov - 18 Nov
Two Bare Feet
room2 Southampton Hometel
Front of property
room2 Southampton Hometel
4.0 star property
9.6 out of 10, Exceptional, (898)
"Great place! "
The price is €95
includes taxes & fees
16 Dec - 17 Dec
room2 Southampton Hometel
Peartree Serviced Apartments
Studio, 1 Queen Bed | Private kitchen
Peartree Serviced Apartments
3.5 star property
9.6 out of 10, Exceptional, (252)
"Lots of parking and an easy self check-in. Our Apartment was spotless and furnished to a very high standard, with crisp bright white bed linens and towels. Probably in our Top 3 accommodation spots across the many places we've stayed worldwide. "
The price is €133
includes taxes & fees
17 Nov - 18 Nov
Peartree Serviced Apartments
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.