Search Deals onWinchester Vacation Packages
Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Fig Tree Shanklin
Price was $1,404, price is now $1,328 per person
$1,328
per person
Nov 30 - Dec 2
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Southampton (SOU)
Stay at this hotel in Shanklin. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Shanklin Theatre and Shanklin Beach are located nearby.
The Elvetham Hotel
Price was $1,943, price is now $1,821 per person
$1,821
per person
Nov 23 - Nov 30
found 2 hours ago
Roundtrip non-stop flight included
New York (JFK) to Southampton (SOU)
Book a stay at this historic hotel in Hook. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions West Green House Garden and North Hants Golf Club are located nearby.
The Bell Inn
Price was $1,785, price is now $1,725 per person
$1,725
per person
Dec 21 - Dec 23
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to Southampton (SOU)
Book a stay at this golf inn in Lyndhurst. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions New Forest National Park and Paultons Family Theme Park - Home of Peppa Pig World are located nearby.
HQ Aparthotel Farnborough
Price was $1,436, price is now $1,390 per person
$1,390
per person
Dec 27 - Jan 4
found 23 hours ago
Roundtrip flight included
New York (NYC) to Southampton (SOU)
Book a stay at this business-friendly aparthotel in Farnborough. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Kingsmead Shopping Centre and St Michaels Abbey are located nearby.
All good apart from the lighting in the room was poor and the kitchen could have more kitchen utensils plates glasses cups etc... as having one each meant constantly cleaning to re use them.
Also more double glazing to make the rooms more quiet would be really good as having deliveries at 6.30am not good.
Reviewed on Oct 10, 2026
DoubleTree by Hilton Southampton
Price was $1,474, price is now $1,429 per person
$1,429
per person
Nov 16 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Southampton (SOU)
Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Southampton Cruise Terminal and WestQuay Shopping Centre are located nearby.
The Montagu Arms Hotel
Price was $1,408, price is now $1,366 per person
$1,366
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Southampton (SOU)
Stay at this hotel in Brockenhurst. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Southampton Cruise Terminal and WestQuay Shopping Centre are located nearby.
Harbour Hotel Southampton
Price was $1,456, price is now $1,416 per person
$1,416
per person
Nov 30 - Dec 2
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Southampton (SOU)
Book a stay at this luxury hotel in Southampton. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Southampton Cruise Terminal and WestQuay Shopping Centre are located nearby.
High Corner Inn
Price was $1,795, price is now $1,769 per person
$1,769
per person
Dec 21 - Dec 23
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to Southampton (SOU)
Book a stay at this business-friendly inn in Ringwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions New Forest National Park and Bolderwood Deer Sanctuary are located nearby.
Great location for walking or just sitting in the garden or around the log fire. Staff were courteous, helpful and friendly. Dinner and breakfast was cooked to perfection, we will be retuning for a 5th visit.
Reviewed on Oct 9, 2026
Winchester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Winchester Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
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