
City of Winchester Vacation Packages
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Your City of Winchester Vacation
With a City of Winchester vacation 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 vacation into a reality.
Top vacation destinations in City of Winchester

Southampton

Winchester
Top City of Winchester Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Jireh House
Price was CA $1,301, price is now CA $1,276 per person
CA $1,276
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Southampton (SOU)
8.8/10 Excellent! (88 reviews)
Attractive old house close to seafront. I had to share a bathroom, but as the house wasn't full this didn't present a problem.
Reviewed on May 31, 2026

Winchester Wessex Hotel by Sunday
Price was CA $2,203, price is now CA $1,892 per person
CA $1,892
per person
Jul 22 - Jul 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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

Forest Park Country Hotel & Inn, Brockenhurst, New Forest
Price was CA $1,658, price is now CA $1,581 per person
CA $1,581
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Southampton (SOU)
9.4/10 Exceptional! (813 reviews)
Good selection buffet breakfast. Great access to New Forest open country right from the hotel.
Reviewed on Jun 8, 2026


Ormonde House Hotel
Price was CA $1,287, price is now CA $1,280 per person
CA $1,280
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Southampton (SOU)
8.6/10 Excellent! (206 reviews)
Really nice stay, staff very helpful and accomodating, we were on the top floor and the room was very warm but the whirlpool bath was an unexpected bonus. Only negative was people smoke just outside the restaurant and bar and with the windows open the smoke came im. A separate smoking area away from the hotel would be better.
Reviewed on Jun 1, 2026
City of Winchester Hotel Deals

New Place
Shirrell Heath Southampton England
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Jul 5 to Jul 6
CA $105
CA $126 total
Jul 5 - Jul 6
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"Just Okay - nothing special - sour milk in the room spoiled the coffee"
Reviewed on Jun 6, 2026

Meon Valley Hotel, Spa & Golf
Sandy Lane Southampton England
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Jun 14 to Jun 15
CA $92
CA $110 total
Jun 14 - Jun 15
includes taxes & fees
7/10 Good! (1,012 reviews)
"The place is nice and value for money, but they have to step up on their cleaning standard"
Reviewed on Jun 8, 2026

The Winchester Hotel & Spa
Worthy Lane Winchester England
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Jun 14 to Jun 15
CA $138
CA $166 total
Jun 14 - Jun 15
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"There was a wedding on , so couldn’t sit outside which was a shame, as air con in the bar was too cold. Didn’t stay and have another drink coz just too cold. Used spa Which was nice, but ladies changing rooms need more space and the floor needed to be cleaned more often. Minor point, but generally ..."
Reviewed on Jun 1, 2026
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.
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







