Hill Head Vacations from $1,903

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Your Hill Head Vacation

The best way to experience this vibrant city is with a tailor-made Hill Head vacation package. Base yourself in the neighborhood of Southampton City Centre, which is great for dining, cafes and bars and pubs or go someplace else — our package deals are all about you. If your trip to Hill Head includes a little sightseeing, hit up renowned attractions like Portchester Castle, Meon Shore Beach and Hill Head Beach. Whoever you're traveling with and whatever you plan to spend, your dream Hill Head vacation is just a few clicks away with Expedia.

The Latest Hill Head vacation packages

Price found within the past 48 hours. Click for updated prices.
The Fig Tree Shanklin

The Fig Tree Shanklin

3.5 out of 5
Price was $2,013, price is now $1,903 per person
$1,903
per person
Jul 21 - Jul 24
found 19 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Southampton (SOU)
9.2/10 Wonderful! (73 reviews)
Reported toilet not flushing before we went out for dinner, staff said they would fix it while we were out, come back not fixed had to phone again they tried again unsuccessfully and only then offered different room this was 9 o'clock in the evening. Think this could have been handled net

Reviewed on Nov 28, 2025

Seaview Holidays - Salterns Village

Seaview Holidays - Salterns Village

4 out of 5
Price was $2,202, price is now $2,041 per person
$2,041
per person
Jul 21 - Jul 24
found 19 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Southampton (SOU)
9/10 Wonderful! (77 reviews)
Very quiet area and kept very tidy beds need to be updated and a quick lick of paint but we would stay again

Reviewed on Sep 29, 2025

The Pilot Boat Inn

The Pilot Boat Inn

3.5 out of 5
Price was $2,023, price is now $1,919 per person
$1,919
per person
Jul 21 - Jul 24
found 19 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Southampton (SOU)
8.2/10 Very Good! (24 reviews)
No breakfast included despite booking confirmation. Room ok but very much in need of repair. Bathroom provisions poor and needed to request additional ‘essentials’ having been left 1/4 a roll.

Reviewed on May 6, 2026

The Royal Hotel

The Royal Hotel

4 out of 5
Price was $2,227, price is now $2,128 per person
$2,128
per person
Jul 21 - Jul 24
found 19 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Southampton (SOU)
9.4/10 Exceptional! (149 reviews)
Excellent location, friendly staff and superb good.

Reviewed on Mar 10, 2026

New Holmwood Hotel

New Holmwood Hotel

3 out of 5
Price was $2,070, price is now $1,984 per person
$1,984
per person
Jul 21 - Jul 24
found 19 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Southampton (SOU)
9/10 Wonderful! (359 reviews)
Clean and comfortable room. Friendly staff

Reviewed on Apr 25, 2026

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Discover the most popular places to visit in Hill Head

Portchester Castle

Portchester Castle

Inspect the fascinating exhibits and climb the spiral staircase to the roof for commanding views of the stunning coastline and the quaint village of Portchester.

Portchester Castle

Segensworth Business Park

After visiting Segensworth Business Park, make a plan to see the other sights and activities in Fareham. Wander the area's waterfront or simply enjoy one of its lively bars.

Segensworth Business Park

Solent Business Park

After visiting Solent Business Park, make a plan to see the other sights and activities in Whiteley. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Solent Business Park

What to do in Hill Head

Stonehenge Tour from Southampton to London

Stonehenge Tour from Southampton to London

$183
per adult
100% of travellers recommend
Stonehenge Tour from Southampton to London
Walk the Secrets of the Titanic

Walk the Secrets of the Titanic

$22
per adult
98% of travellers recommend
Walk the Secrets of the Titanic
Southampton: Guided Ghost Walk

The Southampton Ghost Walk

$20
per adult
100% of travellers recommend
The Southampton Ghost Walk
See all activities in Hill Head

Hill Head Hotel Deals

Leonardo Hotel Southampton

Leonardo Hotel Southampton

4 out of 5
1 Charlotte Place Southampton England
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $85 total per night from May 17 to May 18
$85 total
May 17 - May 18
Total with taxes and fees
8.6/10 Excellent! (1,292 reviews)
I loved my stay at Leonardo! Cosy room, beautifully decorated spaces, and a lovely staff. The location was perfect for me- a short cab or a meandering walk from the rail line, right across the street from stunning parks. My only complaint would be a few missed spills and stains in the room, but the ...

Reviewed on May 6, 2026

Leonardo Hotel Southampton
The Langstone Quays

The Langstone Quays

4 out of 5
Northney Road Hayling Island England
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $118 total per night from May 17 to May 18
$118 total
May 17 - May 18
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
I would describe the stay as travelodge level rooms- fairly basic. Probably a 2-3 star stat. Standard of cleanliness isn’t great- the room had a faint smell of damp or urines. The mugs in the room were also dirty The facilities were surprisingly impressive- a good sized pool and proper gym. We stayed ...

Reviewed on May 6, 2026

The Langstone Quays
The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane Winchester England
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $133 total per night from May 10 to May 11
$133 total
May 10 - May 11
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
The room was really nicely done and I appreciated the little extra touches like biscuits, hot chocolate sachets, and nice bramley toiletries. It was a bit dated in places (eg bathroom door chipped at the bottom, a couple of moths, and noise from other rooms using their water and walking upstairs). ...

Reviewed on May 6, 2026

The Winchester Hotel & Spa
See all 4,359 properties in Hill Head
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.

Find the Best Hill Head Vacation Packages

Hill Head Beach Vacation

Listen to the waves breaking onto the shore and stroll by the sparkling waters on your Hill Head vacation. If you need an escape from everyday life, a trip to Hill Head will work wonders. We have a great range of Hill Head vacation deals to select from. Lock in one close to Hill Head Beach, just 0.2 miles from the city center, and live out your vacation dreams without hurting your budget.

Hill Head Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Southampton Airport (SOU)
Top Sights
Portchester Castle, Hill Head Beach and Westbury Manor Museum

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Frequently asked questions

How much does a Hill Head vacation package cost?
Offering excellent value package deals from $1,903 on Expedia, you'll be pleasantly surprised at how much a vacation to Hill Head costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Hill Head?
If you'd like to snag a cheap Hill Head vacation package, consider planning a trip in January, June and December. You'll usually find lower rates on accommodations and flights during these months — ideal for a budget-friendly break.
How many days is enough for Hill Head?
With a well-planned itinerary, you can easily hit the most popular Hill Head sights in a few days. But if you'd like to discover hidden spots or go on day trips, think about booking your Hill Head vacation for longer.
How to find the best Hill Head package deals?
Start your search for a Hill Head package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Hill Head package deal straight away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Hill Head adventure off to a flying start.
Is it cheaper to book a Hill Head vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels separately. Better still, you can tailor your Hill Head trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Hill Head?
If you're considering a spur-of-the-moment Hill Head trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Hill Head vacation packages?
If you're anything like us, you love traveling but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Hill Head vacation across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.