Winchester Holidays

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Top Flight + Hotel Deals in Winchester

Price found within the past 48 hours. Click for updated prices.
Fernhurst Holiday apartments

Fernhurst Holiday apartments

4 out of 5
Price was €876, price is now €626 per person
€626
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Southampton (SOU)
9.6/10 Exceptional! (4 reviews)
Enchanted Manor

Enchanted Manor

5 out of 5
Save 100% on your flight
Price was €1,237, price is now €844 per person
€844
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Southampton (SOU)
9.6/10 Exceptional! (29 reviews)
Careys Manor & Senspa

Careys Manor & Senspa

4 out of 5
Save 100% on your flight
Price was €1,493, price is now €1,037 per person
€1,037
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Southampton (SOU)
8.4/10 Very Good! (328 reviews)
Near amenities and pleasant surroundings

Reviewed on 12 Aug 2025

The Seaview Hotel

The Seaview Hotel

3 out of 5
Save 100% on your flight
Price was €1,081, price is now €761 per person
€761
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Southampton (SOU)
9.4/10 Exceptional! (12 reviews)
We booked the hotel for our honeymoon. We booked a premium room which was in the Annex at the back of the hotel we liked this as it was nice and quiet and a very spacious room. The room was clean and very comfortable. We visited the hotel restaurant on our first night and the food was delicious and service good. Breakfast was tasty each morning and all of the staff were polite and courteous. Would recommend.

Reviewed on 18 Jun 2025

No.4 Carlton Hotel

No.4 Carlton Hotel

4 out of 5
The Polygon
Save 100% on your flight
Price was €1,257, price is now €885 per person
€885
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Southampton (SOU)
9.6/10 Exceptional! (102 reviews)
Beware. The room next to main entrance is noisy because of traffic and guests check in late at night and out early in the morning.

Reviewed on 25 Aug 2025

Top hotels in Winchester

The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane, Winchester, England
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (1,003 reviews)
"Lovely modern hotel in walking distance, 15mins, to Winchester Centre. A few local pubs close to hotel. Fantastic breakfast and restaurant."

Reviewed on 23 Aug 2025

Get rates
The Winchester Hotel & Spa
Winchester Wessex Hotel by Sunday

Winchester Wessex Hotel by Sunday

4 out of 5
Paternoster Row, Winchester, England
Fully refundableReserve now, pay when you stay
The price is €86 per night from 31 Aug to 1 Sept
€86
31 Aug - 1 Sept
includes taxes & fees
7.4/10 Good! (1,001 reviews)
Our stay
"Didn't eat at hotel mainly good cleanliness however toilet bowl very stained needed bleach and a scrub. Bed comfy nice view basic group ideal for one night"

Reviewed on 17 Aug 2025

Winchester Wessex Hotel by Sunday
voco Winchester Hotel & Spa by IHG

voco Winchester Hotel & Spa by IHG

4 out of 5
Telegraph Way Morn Hill, Winchester, England
Fully refundable
The price is €99 per night from 31 Aug to 1 Sept
€99
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (880 reviews)
"Room is spacious and bed is comfy, room service is excellent (the burger) and the spa is nice. It was a great spot to stay for a wedding!"

Reviewed on 24 Aug 2025

voco Winchester Hotel & Spa by IHG
See all 3,247 properties in Winchester
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.

Popular places to visit

Marwell Zoo featuring dangerous animals and zoo animals

Marwell Zoo

Head out on a safari in search of hippos, snow leopards and giraffes or check out unusual reptiles at this spacious zoo and wildlife park.

Marwell Zoo
Great Hall showing heritage architecture

Great Hall

Admire one of the finest 13th-century halls in England and see the legendary round table of King Arthur at this monument to the city’s medieval heritage.

Great Hall
Hospital of St Cross featuring heritage architecture

Hospital of St Cross

Set within tranquil gardens, England’s oldest charitable institution features traditional 15th-century architecture and a stunning Norman church.

Hospital of St Cross

What to do in Winchester

Journey Through Winchester's Past

Journey Through Winchester's Past

€14
per adult
Journey Through Winchester's Past
Stonehenge Tour from Southampton to London

Stonehenge Tour from Southampton to London

€150
per adult
100% of travellers recommend
Stonehenge Tour from Southampton to London
Courtesy of English Heritage

Southampton: Post-Cruise Tour to London via Salisbury, Stonehenge and Windsor

€226
per adult
88% of travellers recommend
Southampton: Post-Cruise Tour to London via Salisbury, Stonehenge and Windsor
See all activities in Winchester

Frequently asked questions

How much does a Winchester holiday package cost?
You'll find cheap prices from €626 on Expedia for your Winchester escape. However, factors like the hotel choice, length of stay and season will influence how much your holiday to Winchester costs.
What are the cheapest months to go to Winchester?
You're likely to find lower rates and better availability in January, February and November. Take a look at our cheap Winchester holiday packages and you could get some excellent off-season deals.
How many days is enough for Winchester?
Allow around 2 days for your Winchester holiday if you want to take in all that makes this place special. Wander around popular areas, including Littleton and Sparsholt. Then make a beeline for top attractions like Theatre Royal Winchester and Westgate Museum. With a good itinerary, you'll be kept busy with room for some rest and relaxation too. Want to venture outside of Winchester? Consider an excursion or two.
Is it worth booking a holiday package to Winchester?
Well known for its views, nightlife and walking trails, a Winchester holiday has something for everyone. Be sure to check out main sights like Winchester Cathedral and Winchester Christmas Market, and consider renting a set of wheels for day trips to discover even more.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Winchester package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchester escape off to a flying start.
Is it cheaper to book a Winchester holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and stays individually. Better still, you can tailor your Winchester getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Winchester?
Enjoy incredible bargains by reserving your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Winchester getaway.
How to plan a trip to Winchester?

  1. Choose when to get away: Check your diary and pack your bags. Your preferred season and the type of activities on offer will also help you decide when to holiday in Winchester.
  2. Budget wisely: Besides the cost of your hotel, you should factor in other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Winchester.
  3. Decide how long to go for: Now that you're up to speed on Winchester, you can figure out the ideal length of your break. Put together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a tailored Winchester holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.