Name: Winchester Wessex Hotel by Sunday
Price range: CA $168
Rating: 7.6

Your Winchester Vacation

The rich history and welcoming locals are just the start of the things Winchester has on offer. Discover the very best of this city the way you want with a customized Winchester vacation package. If your trip to Winchester includes a little sightseeing, visit popular attractions like Winchester Cathedral, Great Hall and Winchester Christmas Market. Whoever you're escaping with and whatever the size of your budget, your ultimate Winchester vacation is only clicks away with Expedia.

Top Winchester Vacation Deals

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

Red Lion Hotel

CA $1,510

per person

Jun 30 - Jul 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Southampton (SOU)

8.4/10 Very Good! (1,002 reviews)

It was very well presented in all aspects. The kitchen staff were good and helpful. The reception staff were well dressed and presented themselves very professionally rooms were very neat and clean. Would come again when visiting my mother everything is nearby.

Reviewed on May 19, 2026

Winchester Wessex Hotel by Sunday

CA $2,025

per person

Aug 11 - Aug 17

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Southampton (SOU)

7.6/10 Good! (1,002 reviews)

The view of Winchester Cathedral from my bedroom was amazing. All of the staff were extremely helpful and positive including promptly resolving air temperature issues in my room. The room was spotlessly clean. But the room felt rather tired with scratched and battered furniture and a dated bathroom. The decor in the bar and restaurant did not reflect the historic location of the building and seemed very generic and unimaginative

Reviewed on May 22, 2026

Four Seasons Hotel Hampshire

CA $7,005

per person

Jul 16 - Jul 22

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Southampton (SOU)

9.4/10 Exceptional! (243 reviews)

The property is gorgeous, and the staff are all warm, friendly and helpful.

Reviewed on May 23, 2026

Holiday Inn Basingstoke by IHG

CA $1,520

per person

Jun 30 - Jul 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Southampton (SOU)

8.2/10 Very Good! (588 reviews)

On arrival, there was nobody on the reception desk, and after waiting for a short while we had to go and find a staff member to check us in. The rooms whilst dated were clean and comfortable. Having booked a dinner bed and breakfast rate, we were disappointed to find that the dinner options were very limited, due to the hotel being refurbished according to a staff member. Breakfast buffet the following morning was fine, there was a good choice of hot and cold food. The coffee machine was out of beans though and once refilled would not work, which was disappointing. Overall a decent hotel, the main issue being the renovation and an apparent shortage of staff.

Reviewed on May 19, 2026

Apollo Hotel

CA $1,530

per person

Jun 30 - Jul 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Southampton (SOU)

7.2/10 Good! (1,003 reviews)

We had a 1 hr wait for our room to be ready .spacious and clean but tatty and needing redecorating .wallpaper hanging off the walls shabby furniture. Towels and bedding good. below average standard. Bank Holiday weekend booked fora spa weekend and the salon was shut the entire time of our stay. Disappointing. I could not recommend this hotel The staff were brilliant and the best thing about this hotel

Reviewed on May 5, 2026

Things to do in and around Winchester

Winchester offers a delightful blend of outdoor adventures and scenic beauty, making it perfect for a vacation. Key activities include exploring the recreational areas and vibrant public markets, as well as the famous Winchester Christmas Market. Don't miss out on the various shore excursions and unique trips that showcase the charm of this historic city. Whether you're seeking relaxation or adventure, Winchester has something for every traveller.

Shopping

In Winchester, enjoy local shops and boutiques for unique gifts. If you're up for a drive, visit WestQuay Shopping Centre, 19.3km away, for a vibrant shopping experience. Gunwharf Quays, 32.2km away, also offers a mix of outlets and entertainment, perfect for a day trip.

Recreation

The Winchester Science Centre and Planetarium offers an engaging blend of education and fun, perfect for families. Enjoy cultural performances at the Mayflower Theatre, ideal for a romantic night out. For a movie experience, Leisure World provides a relaxed atmosphere for entertainment with loved ones.

Adventure

Experience the thrill of speed at TeamSport Indoor Go Karting Southampton, located 9.7km from Winchester, where you can race against friends on an exciting track. Alternatively, visit Monkey Bizness, 11.3km away, for family-friendly arcade fun and adventure vibes. The Race Centre offers another exciting karting experience, also 9.7km from Winchester.

Nightlife

In Winchester, enjoy a lively nightlife at venues like The Old Gaolhouse and The Rifleman, where you can find cozy pubs and vibrant bars. Stroll along High Street for unique spots and live music, creating a warm atmosphere perfect for a memorable night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Winchester

Winchester offers a delightful blend of outdoor adventures and rich history, making it perfect for your vacation. Explore historic sites such as Winchester Cathedral, visit engaging museums, and discover charming historic houses. With attractions catering to culture and family experiences, you'll find plenty to keep you entertained. Don't miss the chance to immerse yourself in the captivating scenery and vibrant heritage of this remarkable city.

Winchester Cathedral: Experience the grandeur of Winchester Cathedral, a stunning medieval structure with remarkable architecture and rich history. Explore its beautiful stained glass windows and tranquil atmosphere, making it a perfect spot for reflection and cultural appreciation.
Paultons Family Theme Park - Home of Peppa Pig World: A delightful theme park located 20.9km from Winchester, perfect for families. Enjoy thrilling rides and attractions themed around the beloved characters from Peppa Pig, ensuring a fun-filled day for visitors of all ages.
University of Southampton: Situated 14.5km from Winchester, this historic university boasts impressive architecture and beautiful grounds. Explore its vibrant campus and engage with the culture of an esteemed institution known for its research and innovation.

Best time to go to Winchester

The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly cloudy with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	40.3°F (4.6°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
February	41.2°F (5.1°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
March	43.9°F (6.6°C)	Light Rain	Mostly Cloudy	Average	Average
April	47.8°F (8.8°C)	Light Rain	Mostly Cloudy	Average	Average
May	53.2°F (11.8°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
June	59.2°F (15.1°C)	Light Rain	Mostly Cloudy	Average	Average
July	62.8°F (17.1°C)	Light Rain	Mostly Cloudy	Slightly High	Slightly High
August	62.1°F (16.7°C)	Light Rain	Mostly Cloudy	Average	Slightly High
September	58.6°F (14.8°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
October	53.4°F (11.9°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
November	46.8°F (8.2°C)	Light Rain	Mostly Cloudy	Slightly High	Slightly Low
December	43.0°F (6.1°C)	Light Rain	Mostly Cloudy	Slightly Low	Average

Tips to save on your trip to Winchester

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Winchester.
Consider traveling during the off-peak season (typically January to February and November) for more affordable package holidays to Winchester.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Ready to book your vacation to Winchester?

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Winchester Hotel Deals

The Winchester Hotel & Spa

Worthy Lane Winchester England

Fully refundableReserve now, pay when you stay

CA $166

CA $199 total

Jun 7 - Jun 8

includes taxes & fees

8.6/10 Excellent! (1,002 reviews)

"We stayed as a stop over for one night. We selected the hotel based on location and a lift as we had a heavy bag. When we’re arrived all parking was taken so we parked directly in front of the hotel and were told it was council owned and we needed to park and display - no help with finding the park ..."

Reviewed on May 24, 2026

Norton Park Hotel, Spa & Manor House

Sutton Scotney Winchester England

Fully refundableReserve now, pay when you stay

CA $149

CA $179 total

Jun 7 - Jun 8

includes taxes & fees

8/10 Very Good! (1,001 reviews)

"Large room. Good desk. Bathroom smelt a little bit of dump. Food wasn't good: cold vegetables, cold chips, rubbery pizza. Also, the walkway between the bedrooms & the bar/reception was exposed to outside temperature, making too cold / uncomfortable so had to carry a coat - a nuisance."

Reviewed on May 20, 2026

Winchester Wessex Hotel by Sunday

Paternoster Row Winchester England

Fully refundableReserve now, pay when you stay

CA $168

CA $202 total

Jun 8 - Jun 9

includes taxes & fees

7.6/10 Good! (1,002 reviews)

"The view of Winchester Cathedral from my bedroom was amazing. All of the staff were extremely helpful and positive including promptly resolving air temperature issues in my room. The room was spotlessly clean. But the room felt rather tired with scratched and battered furniture and a dated bathroom. ..."

Reviewed on May 22, 2026

See all 3,429 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.