Holiday Homes in City of Winchester

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City of Winchester Accommodation: Most Popular Cities to Stay

Our top choices for City of Winchester holiday homes

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

The Charming Redwood Escape, New Forest

The Charming Redwood Escape, New Forest
Southampton
10.0 out of 10, Exceptional, (1 review)
"Lovely place to stay. Right next to the new forest national park with easy access to so many nearby attractions. Will definitely return again. "
United Kingdom
Geoff
The price is £355
includes taxes & fees
12 Feb - 13 Feb
The Charming Redwood Escape, New Forest

Bermuda House with parking, good sea view and minutes from beach and shops

Bermuda House with parking, good sea view and minutes from beach and shops
Ventnor
9.6 out of 10, Exceptional, (4 reviews)
"Property is in a great location and has all the facilities needed for a large group."
United Kingdom
Helen H.
Bermuda House with parking, good sea view and minutes from beach and shops

Stunning Holiday Home Beautiful Lakeside Views 15 Mins From Goodwood

Stunning Holiday Home Beautiful Lakeside Views 15 Mins From Goodwood
2.0 star property
Chichester
The price is £95
includes taxes & fees
1 Mar - 2 Mar
Stunning Holiday Home Beautiful Lakeside Views 15 Mins From Goodwood

Beautiful home in Birdham, minutes to the beach

Beautiful home in Birdham, minutes to the beach
Birdham
9.8 out of 10, Exceptional, (9 reviews)
"Clive our host was extremely helpful with his knowledge of the area and very accommodating "
United States
robert
Beautiful home in Birdham, minutes to the beach

Oak Tree Cottage, Charming & Rural Home, Heart of the New Forest

Oak Tree Cottage, Charming & Rural Home, Heart of the New Forest
Pilley
10.0 out of 10, Exceptional, (38 reviews)
"Jenny a place was just right for our family of 6..including 2 children….would certainly stay here again "
United Kingdom
ken j.
Oak Tree Cottage, Charming & Rural Home, Heart of the New Forest

Beautiful 2-bed Apart in Southampton

Beautiful 2-bed Apart in Southampton
3.0 star property
Millbrook
Beautiful 2-bed Apart in Southampton

Squirrels Drey

Squirrels Drey
Fareham
10.0 out of 10, Exceptional, (49 reviews)
"Always a perfect stay 🥰"
United States
Clare W.
Squirrels Drey

Northlands Farm & Lakes

Northlands Farm & Lakes
4.0 star property
Chichester
9.2 out of 10, Wonderful, (44 reviews)
"Lovely people, clean chalet including Christmas tree"
United Kingdom
Sam
The price is £155
includes taxes & fees
12 Feb - 13 Feb
Northlands Farm & Lakes

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

New Forest house with large garden, near sea. Perfect for families with children
Lymington
9.0 out of 10, Wonderful, (63 reviews)
"Really clean, warm and comfortable, good Internet, TV, nice garden, good parking.Only slight drawback not enough seating in sitting room. Perhaps another small sofa.Overall it's very good value and we will use it again for a family gathering. "
United Kingdom
Robert R.
New Forest house with large garden, near sea. Perfect for families with children

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

5-bed house: pool, tennis court, walk to beach, 10 acres
Bouldnor
10.0 out of 10, Exceptional, (74 reviews)
"Absolutely stunning property. "
Canada
Rebecca B.
5-bed house: pool, tennis court, walk to beach, 10 acres

Purple Cloud Cottage

Purple Cloud Cottage
3.0 star property
Portsmouth
9.2 out of 10, Wonderful, (5 reviews)
"Great place for what we needed. Would definitely recommend "
United Kingdom
Pete
Purple Cloud Cottage

Open Mind Property - 4BR, 17 Guests & Free Parking

Open Mind Property - 4BR, 17 Guests & Free Parking
Portsmouth
Open Mind Property - 4BR, 17 Guests & Free Parking

New Property - Marble Bridge Farm

New Property - Marble Bridge Farm
Chichester
10.0 out of 10, Exceptional, (3 reviews)
"Very easy to access the house, extremely well equipped, bed’s comfortable. Swimming pool lovely and warm"
United Kingdom
Dave B.
The price is £814
includes taxes & fees
19 Feb - 20 Feb
New Property - Marble Bridge Farm

Stunning 7 Bedroom Escape Near New Forest and Beach - Large Garden - Sleeps 14

Stunning 7 Bedroom Escape Near New Forest and Beach - Large Garden - Sleeps 14
Sway
8.0 out of 10, Very good, (3 reviews)
"Great size, large rooms, decent facilities.Nice location, good communicationIssues with dishwasher and cleanliness of kitchen and crockery/cutlery/glassware "
United Kingdom
Nicole L.
Stunning 7 Bedroom Escape Near New Forest and Beach - Large Garden - Sleeps 14

Waterside Short Term Lets 3 Bedroom Sea Views Hot Tub

Waterside Short Term Lets 3 Bedroom Sea Views Hot Tub
Portsmouth
4.8 out of 10, (3 reviews)
"Absolutely beautiful property, spotlessly clean and loved the jacuzzi (which was set up and ready to go!) parking outside the house and visitor parking if you have more than 2 cars. The host was friendly, responsive and incredibly helpful. Would really recommend! Thanks for saving our new year!"
United Kingdom
Catherine
Waterside Short Term Lets 3 Bedroom Sea Views Hot Tub

Gorgeous home for 12 - Walk to Beach - Sea View

Gorgeous home for 12 - Walk to Beach - Sea View
Chichester
9.2 out of 10, Wonderful, (7 reviews)
"Gorgeous property, had everything we needed. "
United Kingdom
Krista W.
Gorgeous home for 12 - Walk to Beach - Sea View

Fantastic, sociable home in the beautiful village of Brighstone, with hot tub.

Fantastic, sociable home in the beautiful village of Brighstone, with hot tub.
Isle of Wight
10.0 out of 10, Exceptional, (53 reviews)
"We had an amazing holiday - Sarah and Ashley were great welcoming us when we arrived and then helped with queries during the week. We would certainly recommend a great holiday"
United Kingdom
Vanessa D.
Fantastic, sociable home in the beautiful village of Brighstone, with hot tub.

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

Beautiful Tranquil Barn in 14 acres of perfect peace within New Forest district
Fordingbridge
9.8 out of 10, Exceptional, (18 reviews)
"This is one of those rare properties that you almost don't want to review - in case the secret gets out! Really enjoyed our stay here - so much that we've already booked a longer stay for next year.It is as described - a tranquil setting in 14 acres of it's own land - lovely for us and especially for the dog.The spacious premises are well appointed and the barn has a nice 'warm' feel to it"
United Kingdom
Guy G.
Beautiful Tranquil Barn in 14 acres of perfect peace within New Forest district

Secluded rural retreat, close to beach - sleeps 12

Secluded rural retreat, close to beach - sleeps 12
West Sussex
9.2 out of 10, Wonderful, (10 reviews)
"Great property with lots of room for 3 families and good location for exploring the surrounding area."
United Kingdom
Jonathan D.
Secluded rural retreat, close to beach - sleeps 12
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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Top City of Winchester Hotel Reviews

Find out more about City of Winchester

City of Winchester Holiday Homes: Find the Perfect Place


What is the best time to enjoy a holiday home in City of Winchester?

It might be best to get a rental house in when the weather is ideal for enjoying local surroundings. If you go during the off-season months, there might be fewer tourists and often lower rates, like in .


How many holiday homes are available for rent in City of Winchester?

Choose from 1135 beautiful holiday homes in City of Winchester for your getaway.


How much is a holiday home in City of Winchester?

You can find perfect holiday homes in City of Winchester for as low as £95 per night. Holiday home prices vary depending on what time of year you visit, whether the home is in the city centre or near popular sightseeing spots, and what kinds of amenities it offers.


How can I get the best deal on a holiday home in City of Winchester?

Find the best deals on City of Winchester holiday homes by entering dates and the number of travellers in the search bar. You can use the map feature to view prices and more specific locations of several accommodations all at once. Or filter your search results by star rating, price, number of bedrooms, types of amenities, and accessibility features—Expedia offers incredible deals for every budget.


Why should I book a holiday home in City of Winchester?

There’s no better way to spend your well-earned holiday than in a private, cosy City of Winchester holiday home. You’ll be able to fit all travellers in your group and have a place to call home while you explore City of Winchester.


What amenities are available in a private holiday home?

Depending on your budget and the neighbourhood you choose, you’ll find amenities like a private pool, hot tub, free parking, a full-service kitchen or kitchenette, in-home laundry and WiFi. Your City of Winchester holiday won’t be complete without a beautiful view and easy access to popular activities, use our filter to browse our offers.


Why should I book a holiday home with Expedia?

With Expedia, you’ll earn points on every booking and get incredible deals and member prices. Choose from a vast inventory of holiday homes in City of Winchester—and book all your travel in one place. Save even more when you bundle your bookings together. Add a City of Winchester car hire to your holiday property into a holiday package.


What are the cancellation and flexibility options?

We suggest using the “free cancellation” filter during your search to make sure your booking is flexible. Some accommodations accept and refund cancellations within a specific timeframe, while others may be non-refundable. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.

City of Winchester Holiday Homes information

Number of reviews
327
Accommodation
1135 Holiday Homes
Lowest Price
£95
Highest Price
£814

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