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Winchester Vacation Packages

Build your package with 2 more options

Winchester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hampshire Court Hotel & Spa

Hampshire Court Hotel & Spa

4 out of 5
Price was $879, price is now $813 per person
$813
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Southampton (SOU)
Stay at this 4-star spa hotel in Basingstoke. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Mill Field Nature Reserves and Basing House are located nearby.
Hilton Bournemouth

Hilton Bournemouth

4 out of 5
Price was $1,059, price is now $925 per person
$925
per person
Dec 31 - Jan 7
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Southampton (SOU)
Stay at this 4-star spa hotel in Bournemouth. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Poole Harbour and Bournemouth Beach are located nearby.
No.4 Carlton Hotel

No.4 Carlton Hotel

4 out of 5
Price was $1,520, price is now $1,436 per person
$1,436
per person
Dec 19 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Southampton (SOU)
Stay at this 4-star business-friendly hotel in Southampton. Enjoy free breakfast, free WiFi, and an airport shuttle (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Southampton Cruise Terminal and WestQuay Shopping Centre are located nearby.
Warbrook House Heritage Hotel

Warbrook House Heritage Hotel

4 out of 5
Price was $1,333, price is now $1,283 per person
$1,283
per person
Jan 14 - Jan 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Southampton (SOU)
Stay at this 4-star business-friendly hotel in Hook. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Nirvana Spa and California Country Park are located nearby.
Bartley Lodge Hotel

Bartley Lodge Hotel

4 out of 5
Price was $1,339, price is now $1,301 per person
$1,301
per person
Dec 19 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Southampton (SOU)
Stay at this 4-star business-friendly hotel in Southampton. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions New Forest National Park and Paultons Family Theme Park - Home of Peppa Pig World are located nearby.
Novotel Southampton

Novotel Southampton

4 out of 5
Price was $1,285, price is now $1,249 per person
$1,249
per person
Dec 19 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Southampton (SOU)
Stay at this 4-star 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.
Macdonald Botley Park Hotel & Spa

Macdonald Botley Park Hotel & Spa

4 out of 5
Price was $1,276, price is now $1,249 per person
$1,249
per person
Dec 19 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Southampton (SOU)
Stay at this 4-star spa hotel in Southampton. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions WestQuay Shopping Centre and Utilita Bowl are located nearby.
Orange Grove Hotel & Gardens

Orange Grove Hotel & Gardens

3.5 out of 5
Price was $1,395, price is now $1,367 per person
$1,367
per person
Dec 19 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Southampton (SOU)
Stay at this 3.5-star guesthouse in Southampton. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions WestQuay Shopping Centre and Hamble Common Beach are located nearby.

Winchester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hampshire Court Hotel & Spa

Hampshire Court Hotel & Spa

4 out of 5
Price was $609, price is now $572 per person
$572
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Southampton (SOU)
No.4 Carlton Hotel

No.4 Carlton Hotel

4 out of 5
The Polygon
Price was $1,520, price is now $1,436 per person
$1,436
per person
Dec 19 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Southampton (SOU)
Warbrook House Heritage Hotel

Warbrook House Heritage Hotel

4 out of 5
Price was $628, price is now $602 per person
$602
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Southampton (SOU)
Bartley Lodge Hotel

Bartley Lodge Hotel

4 out of 5
Price was $1,339, price is now $1,301 per person
$1,301
per person
Dec 19 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Southampton (SOU)

Winchester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hampshire Court Hotel & Spa

Hampshire Court Hotel & Spa

4 out of 5
Price was $879, price is now $813 per person
$813
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Southampton (SOU)
No.4 Carlton Hotel

No.4 Carlton Hotel

4 out of 5
The Polygon
Price was $1,914, price is now $1,780 per person
$1,780
per person
Dec 26 - Dec 30
just found
Roundtrip non-stop flight included
New York (NYC) to Southampton (SOU)
Bartley Lodge Hotel

Bartley Lodge Hotel

4 out of 5
Price was $1,667, price is now $1,581 per person
$1,581
per person
Dec 26 - Dec 30
just found
Roundtrip non-stop flight included
New York (NYC) to Southampton (SOU)
Warbrook House Heritage Hotel

Warbrook House Heritage Hotel

4 out of 5
Price was $1,333, price is now $1,283 per person
$1,283
per person
Jan 14 - Jan 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Southampton (SOU)