Winsor Vacation Packages
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Your Winsor Vacation
Reserve a Winsor vacation package that has everything you need without any unnecessary extras. Great for dining, cafes and bars and pubs, consider basing yourself in the neighborhood of Southampton City Centre. You'll want to go sightseeing during your trip to Winsor. Find time for major attractions such as New Forest Wildlife Park, The Common and Romsey Golf Club. Stop dreaming and start traveling. Explore the multitude of options on Expedia today and put your Winsor vacation plans in motion!
Top Winsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Winchester Wessex Hotel by Sunday
Price was CA $1,640, price is now CA $1,399 per person
CA $1,399
per person
May 5 - May 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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 Jan 18, 2026
No.4 Carlton Hotel
The Polygon
Price was CA $2,484, price is now CA $2,202 per person
CA $2,202
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Southampton (SOU)
9.6/10 Exceptional! (131 reviews)
Lovely small hotel. Staff very friendly and efficient. Great cooked breakfast.
Reviewed on Jan 3, 2026
Village Hotel Farnborough
Rushmoor District
Price was CA $1,801, price is now CA $1,626 per person
CA $1,626
per person
Mar 28 - Apr 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Southampton (SOU)
8.2/10 Very Good! (1,001 reviews)
Staff were friendly and professional, room was spacious and well appointed. An excellent experience
Reviewed on Dec 28, 2025
Best Western Chilworth Manor Hotel
Price was CA $1,811, price is now CA $1,671 per person
CA $1,671
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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 Feb 10, 2026
Winsor Hotel Deals
Leonardo Royal Southampton Grand Harbour
West Quay Road Southampton England
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Feb 22 to Feb 23
CA $104
CA $125 total
Feb 22 - Feb 23
includes taxes & fees
8.6/10 Excellent! (1,736 reviews)
Great hotel, polite staff and we had a lovely stay
Reviewed on Feb 5, 2026
Leonardo Hotel Southampton
1 Charlotte Place Southampton England
Fully refundableReserve now, pay when you stay
The price is CA $83 per night from Feb 22 to Feb 23
CA $83
CA $100 total
Feb 22 - Feb 23
includes taxes & fees
8.4/10 Very Good! (1,259 reviews)
Lovely staff, well equipped room and excellent breakfast choices. Room layout was a bit odd but perfectly ok.
Reviewed on Feb 11, 2026
Moxy Southampton
Harbour Parade Southampton England
Fully refundableReserve now, pay when you stay
The price is CA $91 per night from Mar 8 to Mar 9
CA $91
CA $109 total
Mar 8 - Mar 9
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
The room was great with two double beds and two tv’s for each bed, very clean and modern and a good location for our visit to the mayflower theatre
Reviewed on Feb 3, 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.
Discover the most popular places to visit in Winsor
Southampton Cruise Terminal
One of the busiest cruise ports in England is just a few steps from the historical and entertainment attractions of Southampton.
University of Southampton
Tour an oceanographic research institute, watch independent theater productions and see designs by notable British architects at this 150-year-old university.
Mayflower Theatre
From touring West End musicals to magic shows, stand-up comedy to children’s entertainment, this historic theater serves up Southampton’s best entertainment.
What to do in Winsor
Isle of Wight: Osborne Admission Ticket
CA $16
per traveller
100% of travellers recommend
Private Southampton Walking Tour
CA $39
per adult
100% of travellers recommend
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- Brownwich Beach
- Bursledon Brickworks Industrial Museum
- Visit Cadnam
- Calshot Beach
- City Museum
- Grosvenor Casino
- Highcliffe Castle
- Hospital of St Cross
- Visit Landford
- Lepe Beach
- Lower Swanwick Vacations
- Mayflower Park
- Visit New Forest District
- Visit North Baddesley
- Old City Walls
- Paultons Family Theme Park - Home of Peppa Pig World
- Queen's Park
- Riverside Park
- Salisbury Cathedral
- Salisbury Museum
- Salisbury Vacations
- Seacity Museum
- Sir Harold Hillier Gardens
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- Tudor House and Garden
- Winchester Cathedral
- Winchester City Mill
- Winchester Science Centre and Planetarium
- Winchester Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
