City of Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £335 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Your City of Winchester Holiday

With a City of Winchester holiday package, you can forget about planning stresses and put all your energy into experiencing what this lively destination has to offer. You can expect to have a must-visit list as long as your arm during your trip to City of Winchester. One top city you'll want to explore is Winchester. If you're ready to stop dreaming and start packing, Expedia will help turn your City of Winchester holiday into a reality.

Top destinations in City of Winchester

Southampton which includes heritage architecture, a castle and heritage elements
FlightsFlightsHotelsHotels

Southampton

Southampton

Top City of Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Best Western Chilworth Manor Hotel

Best Western Chilworth Manor Hotel

3 out of 5
Price was £339, price is now £288 per person
£288
per person
20 Apr - 24 Apr
found 21 hours ago
Return flight included
Manchester (MAN) to Southampton (SOU)
8/10 Very Good! (1,002 reviews)
Room was very cold on arrival and took 2 hours to warm up - staff were super helpful but having the room out of action for the evening is just unacceptable

Reviewed on 10 Feb 2026

Winchester Wessex Hotel by Sunday

Winchester Wessex Hotel by Sunday

4 out of 5
Save 100% on your flight
Price was £1,015, price is now £693 per person
£693
per person
1 May - 11 May
found 3 hours ago
Return flight included
Manchester (MAN) to Southampton (SOU)
7.4/10 Good! (1,002 reviews)
Great staff on reception. Very convenient location. Room was clean and well equipped.

Reviewed on 18 Jan 2026

Bartley Lodge Hotel

Bartley Lodge Hotel

4 out of 5
Price was £400, price is now £319 per person
£319
per person
20 Apr - 24 Apr
found 21 hours ago
Return flight included
Manchester (MAN) to Southampton (SOU)
7.6/10 Good! (267 reviews)
Lovely hotel stayed many times

Reviewed on 16 Nov 2025

No.4 Carlton Hotel

No.4 Carlton Hotel

4 out of 5
The Polygon
Price was £776, price is now £624 per person
£624
per person
20 Apr - 24 Apr
found 21 hours ago
Return flight included
Manchester (MAN) to Southampton (SOU)
9.6/10 Exceptional! (131 reviews)
Lovely small hotel. Staff very friendly and efficient. Great cooked breakfast.

Reviewed on 3 Jan 2026

The Bitterne Park Hotel

The Bitterne Park Hotel

3 out of 5
Price was £481, price is now £418 per person
£418
per person
20 Apr - 24 Apr
found 21 hours ago
Return flight included
Manchester (MAN) to Southampton (SOU)
6/10 (22 reviews)
Although the outside looks run down, the refurb in the rooms is nice. Once outside is freshened up, a few hanging baskets, tidy up etc, it will look more inviting. Just need a few tweaks. We were in room 7, twin room. Needs a bedside cabinet between the beds . Maybe a dressing table and mirror, for when you're getting ready. Shelf in bathroom would be handy. Bathroom needed cleaning around the floor edge. Bedroom could have done with a hoover. Bed soooo comfy. The lady greeted us and got our room ready early for us. Pub garden is fabulous. We ate at the pub. Best wrap i ve ever had. Will definitely stay again. Thankyou

Reviewed on 3 Jun 2024

City of Winchester Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Southampton Airport (SOU)
Population
46,100
Top Sights
Marwell Zoo, Hill Head Beach and Meon Shore Beach

Top hotels in City of Winchester

The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane Winchester England
Fully refundableReserve now, pay when you stay
The price is £91 per night from 22 Feb to 23 Feb
£91
22 Feb - 23 Feb
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Room spotless Spa great edition Food good

Reviewed on 2 Feb 2026

The Winchester Hotel & Spa
Norton Park Hotel, Spa & Manor House

Norton Park Hotel, Spa & Manor House

4 out of 5
Sutton Scotney Winchester England
Fully refundableReserve now, pay when you stay
The price is £86 per night from 22 Feb to 23 Feb
£86
22 Feb - 23 Feb
includes taxes & fees
7.8/10 Good! (1,001 reviews)
The room was very clean, and the facilities were fantastic

Reviewed on 3 Feb 2026

Norton Park Hotel, Spa & Manor House
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 £65 per night from 15 Feb to 16 Feb
£65
15 Feb - 16 Feb
includes taxes & fees
7.4/10 Good! (1,008 reviews)
Big room

Reviewed on 8 Feb 2026

Winchester Wessex Hotel by Sunday
See all 5,480 properties in City of 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a City of Winchester travel package cost?
Discover the best of City of Winchester from as little as £288. Choose from a wonderful selection of rental cars, hotels and flights to suit your budget. You can score even better deals when you add some experiences or tours to your travel package.
If I'm not able to travel, can I cancel my City of Winchester travel package?
Yes, you can. We realise life happens, so we're happy to help if you need to make changes to your City of Winchester travel package. You may be able to amend or cancel your itinerary for free if you've booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to City of Winchester?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got them all. Select a combination that best suits you and see your savings pile up. We know a package deal is never one-size-fits-all. That's why Expedia offers over 550 air carriers and 1,000,000 properties throughout the world, which lets you customize your City of Winchester holiday.
Does Expedia offer Book Now, Pay Later City of Winchester holidays?
Expedia has partnered with online lender Klarna to make your next getaway easier on your wallet. Paying in instalments means you can spread the costs of your dream holiday, leaving you with more money to spend while you're travelling. Klarna has several payment plans to pick from, so you're sure to find one that works with your budget. Browse these flexible payment options:

  • Pay monthly holidays: Klarna has easy monthly payment plans that work for all types of budgets, so you can jet away on that well-earned holiday sooner.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Consider this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: When you stumble on an unbeatable deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock in your getaway.

Where should I stay in City of Winchester?
You'll fall in love with Winchester. Well-known attractions, like Winchester Cathedral and Great Hall, will keep you on the go in this lively city.
What are the top hotels in City of Winchester?
For properties in Winchester with friendly service and cosy beds, you can't beat St Johns Croft and The Old Vine. If you're stopping by Fareham as well, you can look forward to a good night's sleep at St Johns Croft or Meon Valley Hotel, Golf & Country Club.
How far in advance should I book my City of Winchester holiday?
Savvy travellers often book early. You can normally look up international airfares on Expedia up to 12 months before your flight. If you're purchasing your ticket at the last minute, don't stress. Discounted prices sometimes occur just weeks before departure dates.
What does an Expedia City of Winchester travel package include?
You can choose from any combination of hotels, rental cars and flights. Once you've made your booking, you can also add on activities and tours. Want to pick your airfare class? That's also easy to do. The choice is yours when it comes to planning your ideal City of Winchester trip.
What should I know before booking a City of Winchester travel package?
So many places to go, so many things to see. With a package, you'll be able to cross more of them off your list. Bundle your flights, rental cars and hotels and make big savings.
Can I choose my airline with a City of Winchester Expedia travel package?
You can, and with more than 550 airlines to pick from across the globe, you have loads of choice. Have a look through the available options and find out which airline fits your budget and needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.