Old Town Vacations from $580
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The Latest Old Town Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Medehamstede Hotel
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Southampton (SOU)
7.6/10 Good! (126 reviews)
Clean and comfortable, it made us feel at home even if only for one night. Many thanks to the gentleman at the reception who, despite being tired, kindly waited for us until the very last moment late at night to check us in.
Reviewed on Jul 14, 2025
HQ Aparthotel Farnborough
Rushmoor District
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Southampton (SOU)
9/10 Wonderful! (432 reviews)
The apartments are very clean and lots of the kitchen untencips and small electrics look unused.
Bathroom is modern, clean and spacious.
Reviewed on Aug 9, 2025
Barton's Mill
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Southampton (SOU)
9.4/10 Exceptional! (178 reviews)
Barton’s Mill was a fantastic find. Very friendly staff. Fabulous breakfast. We liked the fact the rooms were separate from the pub and easily accessible. Situated in a beautiful area. Easy access to M3. Would definitely recommend.
Reviewed on Jul 11, 2025
The Jolly Drover
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Southampton (SOU)
9.4/10 Exceptional! (175 reviews)
The pub was pleasant and lively and we enjoyed a good dinner. The room was on the small side but it had all the amenities we needed. The breakast was freshly cooked and excellent.
Reviewed on Aug 7, 2025
Where to stay in Old Town
Find the best Old Town areas and neighborhoods for the activities you enjoy most. Learn more about Old Town
Southampton City Centre
4 out of top 10 points of interest in this area
4.5/5(148 area reviews)
The area was rebuilt after being annihilated in World War II, but the city won’t soon forget its earlier role with the Titanic, seafaring voyages, Romans and Saxons.
Old Town Hotel Deals
The Star Hotel
26 High Street, Southampton, England
7.6/10 Good! (930 reviews)
Good for a 3 star, little dated
"Breakfast was limited, filter coffee only. Bathroom window just had a net curtain and was overlooked so didn’t use shower"
Reviewed on Aug 8, 2025
Ennios Boutique Hotel Rooms
Town Quay Road, Southampton, England
9.4/10 Exceptional! (228 reviews)
"Stayed here prior to our cruise sailing. Walkable to terminal. We were so impressed. Lovely boutique and each room is unique and the attention to detail was superb. Delightful true Southampton feel with high end quality touches. We saw our ship from our window! The bar downstairs was cozy and dinner ..."
Reviewed on Aug 7, 2025
The Winchester Hotel & Spa
Worthy Lane, Winchester, England
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $143 total per night from Aug 21 to Aug 22
$143 total
Aug 21 - Aug 22
Total includes taxes and fees
8.4/10 Very Good! (1,002 reviews)
"A lovely weekend's stay at this hotel. Tranquil environment, friendly, welcoming staff, ideal location for visiting Winchester."
Reviewed on Aug 8, 2025
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 Old Town
Tudor House and Garden
Peer back into the day-to-day lives of Southampton’s Norman and Tudor residents at the city’s most important historic house, garden and ruins.
Medieval Merchant's House
This surviving treasure provides a rare glimpse of a typical medieval English townhouse and offers a simpler alternative to the ornate Tudor House.
Southampton Cruise Terminal
One of the busiest cruise ports in England is just a few steps from the historical and entertainment attractions of Southampton.
Things to do
Stonehenge Tour from Southampton to London
$176
per adult
100% of travellers recommend
Southampton: Post-Cruise Tour to London via Salisbury, Stonehenge and Windsor
$264
per adult
88% of travellers recommend
Walk the Secrets of the Titanic
$22
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.