Headley Down Vacations from $6,159

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The Latest Headley Down vacation packages

Price found within the past 48 hours. Click for updated prices.
Winchester Wessex Hotel by Sunday

Winchester Wessex Hotel by Sunday

4 out of 5
Price was $6,353, price is now $6,159 per person
$6,159
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip flight included
Greenville (GSP) to Southampton (SOU)
7.4/10 Good! (1,003 reviews)
Central location, but hotel rooms are dated and the bathrooms are poor and desperate for updating.

Reviewed on Aug 31, 2025

Quob Park The Old House Hotel & Spa

Quob Park The Old House Hotel & Spa

2.5 out of 5
Price was $7,337, price is now $6,712 per person
$6,712
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip flight included
Greenville (GSP) to Southampton (SOU)
9.4/10 Exceptional! (40 reviews)
Super staff, very welcoming. Room large with excellent quality linen and towels. Breakfast was fabulous

Reviewed on Aug 1, 2025

No.4 Carlton Hotel

No.4 Carlton Hotel

4 out of 5
The Polygon
Price was $6,911, price is now $6,534 per person
$6,534
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip flight included
Greenville (GSP) to Southampton (SOU)
9.6/10 Exceptional! (104 reviews)
This "boutique style hotel" is awesome. The staff go way above and beyond. The rooms are exquisite.We stayed here twice to this month, and both times were excellent. The hotel is close to the cruise port.We highly recommend this hotel for your stay in Southampton.

Reviewed on Aug 30, 2025

The Montagu Arms Hotel

The Montagu Arms Hotel

4 out of 5
Price was $7,037, price is now $6,763 per person
$6,763
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip flight included
Greenville (GSP) to Southampton (SOU)
9.4/10 Exceptional! (177 reviews)
Beautiful property in a very pretty village in the New Forest

Reviewed on Jul 13, 2025

Hotel du Vin & Bistro Winchester

Hotel du Vin & Bistro Winchester

4 out of 5
Price was $6,969, price is now $6,719 per person
$6,719
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip flight included
Greenville (GSP) to Southampton (SOU)
9/10 Wonderful! (532 reviews)
No lift, but otherwise a good standard four star experience. Staff are friendly and efficient.

Reviewed on Aug 20, 2025

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Headley Down Hotel Deals

Village Hotel Basingstoke

Village Hotel Basingstoke

4 out of 5
Basing View, Basingstoke, England
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $96 total per night from Sep 19 to Sep 20
$96 total
Sep 19 - Sep 20
Total with taxes and fees
Village Hotel Basingstoke
The Hog's Back Hotel & Spa Farnham

The Hog's Back Hotel & Spa Farnham

3 out of 5
Seale, Farnham, England
Fully refundableReserve now, pay when you stay
Get rates
The Hog's Back Hotel & Spa Farnham
Red Lion Hotel

Red Lion Hotel

3 out of 5
Red Lion Lane, Basingstoke, England
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $73 total per night from Sep 5 to Sep 6
$73 total
Sep 5 - Sep 6
Total with taxes and fees
Red Lion Hotel
See all 1,093 properties in Headley Down
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.

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Frequently asked questions

How much does a Headley Down vacation package cost?
You'll find cheap prices from $6,159 on Expedia for your Headley Down getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Headley Down costs.
What are the cheapest months to go to Headley Down?
You can generally find lower rates and greater availability in November, December and January. Check out our cheap Headley Down vacation packages and you could get some great off-season discounts.
How many days is enough for Headley Down?
The ideal duration for your Headley Down vacation depends on what you'd like to do and see. Usually, a few days to a week will give you enough time to visit all the major sights and explore some hidden gems along the way.
How to find the best Headley Down package deals?
Start your search for a Headley Down package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Headley Down package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Headley Down adventure off to a flying start.
Is it cheaper to book a Headley Down vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and accommodations separately. Better still, you can customize your Headley Down escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Headley Down?
Land amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Headley Down vacation.
Does Expedia offer Book Now, Pay Later Headley Down vacation packages?
Jet off on your dream trip to Headley Down with help from our Book Now, Pay Later vacations. No need to save like crazy or hold off until your next paycheck — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no hidden or late payment fees, you can easily stick to your budget and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.