City of Winchester holiday lettings and accommodation - HomeToGo base64Hash City of Winchester holiday lettings and accommodation - HomeToGo

City of Winchester holiday lettings and accommodation

Find 1,049 available offers from 16 partners
Anytime
Guests
Anytime
Guests

Top 15 Recommended holiday lettings in Winchester

Find your perfect holiday home, apartment or cottage in Winchester from just £38 per night!

Cottage Ovington
Cottage ∙ 4 guests ∙ 2 bedrooms

Children-friendly beautiful cottage with terrace, BBQ & garden | Pets are welcome

Ovington, Itchen Stoke and Ovington, City of Winchester
from £138
per night
Outstanding(34 ratings)
Vrbo
from £138
per night
View deal
Vrbo
Cottage Cheriton
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage with terrace, garden & BBQ

Cheriton, City of Winchester, United Kingdom
from £116
per night
Outstanding(39 ratings)
HomeToGo
from £116
per night
View deal
HomeToGo
House Winchester
House ∙ 6 guests ∙ 2 bedrooms

Holiday home with barbeque, terrace & garden | City view

Winchester, City of Winchester, United Kingdom
from £151
per night
Outstanding(41 ratings)
Vrbo
from £151
per night
View deal
Vrbo
Apartment Pitt
Apartment ∙ 127 guests ∙ 3 bedrooms

Charming apartment with garden, terrace & jacuzzi | Pets allowed

Pitt, Hursley, City of Winchester
from £130
per night
Very good
Agoda
from £130
per night
View deal
Agoda
Apartment Winchester
Apartment ∙ 2 guests ∙ 1 bedroom

Fully equipped holiday apartment

Winchester, City of Winchester, United Kingdom
from £81
per night
Outstanding(8 ratings)
Vrbo
from £81
per night
View deal
Vrbo
Cottage Beauworth
Cottage ∙ 4 guests ∙ 2 bedrooms

Child-friendly cottage with barbeque & garden | River view | Pet-friendly

Beauworth, City of Winchester, United Kingdom
from £178
per night
HomeToGo
from £178
per night
View deal
HomeToGo
Cottage Ovington
Cottage ∙ 2 guests ∙ 1 bedroom

Cottage with garden

Ovington, Itchen Stoke and Ovington, City of Winchester
from £39
per night
Good(7 ratings)
HomeToGo
from £39
per night
View deal
HomeToGo
Cottage Hambledon
Cottage ∙ 2 guests ∙ 1 bedroom

Beautiful cottage with terrace & garden

Hambledon, City of Winchester, United Kingdom
from £71
per night
Outstanding(5 ratings)
HomeToGo
from £71
per night
View deal
HomeToGo
Apartment Winchester
Apartment ∙ 2 guests ∙ 1 bedroom

Holiday apartment | Nature view

Winchester, City of Winchester, United Kingdom
from £72
per night
Very good(1 rating)
HomeToGo
from £72
per night
View deal
HomeToGo
Cottage Bishop's Waltham
Cottage ∙ 5 guests ∙ 3 bedrooms

Cottage with garden, barbeque & terrace

Bishop's Waltham, City of Winchester, United Kingdom
from £104
per night
Outstanding(31 ratings)
Vrbo
from £104
per night
View deal
Vrbo
Cottage Twyford
Cottage ∙ 2 guests ∙ 1 bedroom

Cottage with barbecue, garden & terrace

Twyford, City of Winchester, United Kingdom
from £93
per night
Outstanding(96 ratings)
Vrbo
from £93
per night
View deal
Vrbo
House Kings Worthy
House ∙ 4 guests ∙ 2 bedrooms

House with barbeque & garden | City view

Kings Worthy, City of Winchester, United Kingdom
from £142
per night
Outstanding(18 ratings)
Vrbo
from £142
per night
View deal
Vrbo
Lodge Pitt
Lodge ∙ 4 guests ∙ 2 bedrooms

Lodge with barbeque, jacuzzi & terrace

Pitt, Hursley, City of Winchester
from £140
per night
Very good(4 ratings)
Vrbo
from £140
per night
View deal
Vrbo
Lodge Pitt
Lodge ∙ 4 guests ∙ 2 bedrooms

Lodge with garden, terrace & BBQ

Pitt, Hursley, City of Winchester
from £121
per night
Outstanding(6 ratings)
Vrbo
from £121
per night
View deal
Vrbo
Apartment Winchester
Apartment ∙ 4 guests ∙ 1 bedroom

Flat with garden | Nature view

Winchester, City of Winchester, United Kingdom
from £92
per night
Excellent(48 ratings)
Vrbo
from £92
per night
View deal
Vrbo

Best holiday lettings with a pool

House  Kings Worthy
from £792 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with barbeque, terrace & private pool | Good for workation

Kings Worthy, City of Winchester, United Kingdom
Pool
Vrbo
View deal
Villa  Soberton
from £1,129 per night
Villa ∙ 15 guests ∙ 6 bedrooms

Villa with barbecue, garden & jacuzzi | Perfect for remote work

Soberton, City of Winchester, United Kingdom
Pool
Vrbo
View deal
House  Kings Worthy
from £1,448 per night
House ∙ 12 guests ∙ 6 bedrooms

Ample holiday home with private pool, terrace & barbecue | Good for workation | Dogs allowed

Kings Worthy, City of Winchester, United Kingdom
Pool
Agoda
View deal
See all offers

Recommended pet-friendly holiday lettings

Cottage  Denmead
from £128 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Fully equipped cottage with barbecue, garden & hot tub | Dogs allowed

Denmead, City of Winchester, United Kingdom
Pet-friendly
HomeToGo
View deal
Cottage  Ovington
-25%
£138
from £103 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Family-oriented cottage with terrace, garden & BBQ | Pets allowed

5.0
Outstanding(34 ratings)
Ovington, Itchen Stoke and Ovington, City of Winchester
Pet-friendly
HomeToGo
View deal
Cottage  Cheriton
from £120 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Fully equipped cottage with BBQ, garden & terrace | Dogs allowed

5.0
Outstanding(39 ratings)
Cheriton, City of Winchester, United Kingdom
Pet-friendly
Vrbo
View deal
See all offers

Best holiday rentals with a balcony

Cottage  Bishop's Waltham
from £103 per night
Cottage ∙ 5 guests ∙ 3 bedrooms

Family-oriented pleasant cottage with barbecue, garden & terrace

5.0
Outstanding(31 ratings)
Bishop's Waltham, City of Winchester, United Kingdom
Balcony
HomeToGo
View deal
Cottage  Winchester
from £167 per night
Cottage ∙ 2 guests ∙ 2 bedrooms

Cottage with garden & terrace

5.0
Outstanding(4 ratings)
Winchester, City of Winchester, United Kingdom
Balcony
Vrbo
View deal
House  Droxford
from £187 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with garden

5.0
Outstanding(2 ratings)
Droxford, City of Winchester, United Kingdom
Balcony
Vrbo
View deal
See all offers

Budget-friendly Holiday Homes in Winchester

Find Fantastic yet Cheap Lettings

Cottage Winchester
from £201 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Child-friendly cottage with terrace & garden | City view | Perfect for remote work

5.0
Outstanding(7 ratings)
Winchester, City of Winchester, United Kingdom
Vrbo
View deal
House Hambledon
from £251 per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped wonderful holiday home with barbeque & garden | Suitable for remote work

5.0
Outstanding(1 rating)
Hambledon, City of Winchester, United Kingdom
Vrbo
View deal
House Winchester
from £265 per night
House ∙ 7 guests ∙ 4 bedrooms

House with terrace, BBQ & garden | City view

5.0
Outstanding(20 ratings)
Winchester, City of Winchester, United Kingdom
Vrbo
View deal

Top-Rated Lettings and Properties in Winchester

Book Holiday Letting Offers with the Highest User Rating

Cottage Winchester
from £144 per night
Cottage ∙ 2 guests ∙ 2 bedrooms

Family-friendly cottage with terrace & garden

5.0
Outstanding(4 ratings)
Winchester, City of Winchester, United Kingdom
HomeToGo
View deal
House Winchester
from £347 per night
House ∙ 7 guests ∙ 3 bedrooms

Holiday home with garden, barbecue & terrace

4.5
Excellent(4 ratings)
Winchester, City of Winchester, United Kingdom
Vrbo
View deal
House Durley
from £433 per night
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented nice holiday home with barbecue, terrace & garden | Pet-friendly

4.5
Excellent(4 ratings)
Durley, City of Winchester, United Kingdom
Vrbo
View deal

Customer ratings and reviews

How are reviews collected?
Sietze v.
Guest verified by HomeToGo

Newly built (and thus modern) cottage, well equipped and in a very nice and quiet place. Friendly host lives in his own cottage nearby.

Reviewed on 15/08/2023 | Couple
Cottage Soberton
from £78 per night
HomeToGo
Cottage ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding(1 rating)
Soberton, City of Winchester, United Kingdom
View deal

Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform holiday planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in Winchester

  • Pet-friendly (397)
  • Parking (17)
  • WiFi (958)
  • Kitchen (579)
  • Pool (104)
  • Garden (640)
  • TV (785)
  • Balcony/patio (428)
  • Hot tub (69)
  • Washing machine (418)
  • No smoking (929)
  • Fireplace (204)

If you have a pet, you can easily find a pet-friendly holiday rental in City of Winchester. Pet-friendly holiday rentals in City of Winchester have an average price of £264 per night. If you prefer to stay central, a few of the pet-friendly lettings are less than 2 kilometres away from the city centre.

Explore the historic city of Winchester with a cosy holiday letting

The former seat of King Alfred the Great, Winchester offers you a unique mix of country and city. This historic town was the birthplace of cricket and boasts fine architecture, as well as a vibrant contemporary art scene.

Holiday cottages in Winchester allow you to explore everything this city has to offer with all the comforts of home. There are different types of holiday lettings on offer, right from manors and river front houses to chalets and cabins.

What are the best activities for families in Winchester?

Fun activities to do with kids

Your kids will love visiting the more than 1,200 animals at the Marwell Zoo, which is located just around 8 km outside of Winchester. This zoo is famous for its conservation of endangered animals such as Oryx and white rhinos.

Winchester Science Centre and Planetarium will keep your kids engaged for hours with over 100 hands-on exhibits. The planetarium offers a fantastic selection of films that are projected on to a 360 degree domed screen.

What are the best places to discover the arts and culture of City of Winchester?

Historical attractions in Winchester

Winchester Cathedral is a treasure trove of historical artefacts, and the foundations of the building itself date back to the 7th century. This cathedral offers you attractions like the 12th century Winchester Bible, the tomb of Jane Austen, and 16th century murals decorating the Lady Chapel.

All fans of the Arthurian legend must pay a visit to the Winchester Castle to marvel at King Arthur’s Round Table that is affixed to the back wall of the Great Hall. This castle was built during William the Conqueror’s reign and dates back to the 11th century.

Information about holiday rentals in Winchester

🏡 Holiday homes available 1,049 rentals
💳 Discounts available up to 25%
🌙 Nightly prices from £39
⭐ Popular amenities Pets allowed, Parking and Internet
🐾 Pet friendly rentals 397 properties
🏊 Holiday rentals with pools 104 properties
46 reviews
City of Winchester holiday rentals have an average rating of 5/5 across 46 reviews left by travellers.

Frequently Asked Questions

What is the average nightly price for a holiday rental in Winchester?

The nightly price in Winchester is £39 on average. The average cost of cottage is £243 per night. House rentals costs around £358 per night.

How many holiday homes are available to rent in Winchester?

Most of House rentals and Cottage are usually available during November in Winchester.

What is the most popular holiday home amenity in Winchester?

The top three amenities our customers choose for holiday rentals in Winchester are Pets allowed, Parking and Internet.

How many holiday rentals with a pool there are on offer in Winchester?

Holiday apartments with pools are 10 of all offers in Winchester for an average price of £315 per night.

Am I allowed to bring my pet while staying in aholiday apartment in Winchester?

Searching for accommodation in Winchester for you and your pet is easy with 397 pet-friendly holiday homes available on HomeToGo.

What is the best time of year to travel to City of Winchester?

Book your City of Winchester holiday in May or July to avoid a washout; these are the months with the least amount of rain.

How do I find discounts on holiday homes in Winchester?

You can find great value holiday accommodation in Winchester with the nightly price of a letting beginning at £39 - and HomeToGo has created a range of features that mean it's easy to locate some outstanding offers. When choosing the dates for a trip, try a search using HomeToGo's flexible dates technology to quickly locate lower cost date options and get discounts of up to 25%. Furthermore, HomeToGo's 'distance from' filter makes it easy to discover hidden gem holiday homes in great value, lesser-known spots with good proximity to your desired destination, whether that's the coastline, a swimming lake, winter sports area or town centre. Start searching with time to spare to get the best of good availability and the best deals - and do so with confidence by using HomeToGo's 'free cancellation' filter as you look for the perfect holiday home.

What are the benefits of choosing a holiday letting in Winchester with HomeToGo?

From increased privacy away from the crowds to more space in which to have fun with your family, friends or partner, holiday rentals in Winchester provide many advantages. HomeToGo provides real reviews written by previous guests, and searching is safe, simple, and stress-free - so with 1,049 lets from 16 providers in the vicinity, you're sure to locate the perfect type of accommodation with all of the amenities to suit you in Winchester.

Top cities to visit

Discover Nearby Regions Worth Exploring

Most Popular Destinations

Show more
image-tag