Headley Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Headley Vacation Deals
Price found within the past 48 hours. Click for updated prices.
St Leonard's Hotel by Greene King Inns
CA $1,223
per person
Oct 29 - Nov 5
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Southampton (SOU)
8/10 Very good! (705 reviews)
Stayed at st Leonards hotel as a stopover before travelling to the isle of wight. Very comfortable. Food reasonable prices and staff very polite
Reviewed on Sep 21, 2026
Colebrook Guest House
Rushmoor District
CA $1,107
per person
Dec 3 - Dec 9
found 19 hours ago
Roundtrip flight included
Calgary (YYC) to Southampton (SOU)
8.8/10 Excellent! (226 reviews)
Perfect location for the Farnborough exhibition Centre
Good quality breakfast
Easy check in
On street parking
Reviewed on Sep 9, 2026
Ready to book your vacation to Headley?
Headley Hotel Deals
Village Hotel Bracknell
Bagshot Road Bracknell England
Fully refundableReserve now, pay when you stay
CA $92
CA $110 total
Oct 11 - Oct 12
includes taxes & fees
8/10 Very good! (939 reviews)
"Staff were welcoming and answered all my questions with ease. Parking and charging on site was simple, the gym was well equipped and the restaurant had a great choice, good staff and high quality. I had nothing to complain about for a one night business trip it was ideal."
Reviewed on Sep 21, 2026
Harbour Hotel Guildford
3 Alexandra Terrace, High Street Guildford England
Fully refundableReserve now, pay when you stay
CA $209
CA $251 total
Oct 22 - Oct 23
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"The hotel was very comfortable, and its location near the city center made it easy to get anywhere we wanted to go. I'm giving 4 stars instead of 5 for one reason. Our room was advertised as a nice window room, but the window looked into a dirty structure with barbed wire, inside the building, overlooking ..."
Reviewed on Sep 20, 2026
Macdonald Frimley Hall Hotel and Spa
Lime Avenue, Off Portsmouth Road Camberley England
Fully refundableReserve now, pay when you stay
CA $122
CA $146 total
Oct 11 - Oct 12
includes taxes & fees
8/10 Very good! (997 reviews)
"This visit was only a one night quick overnight as we were attending the golf at Wentworth. Arrived quite late and left early. The rooms are spotlessly clean with a lovely comfortable bed with high quality bedding. The bathroom is very nice with a great size shower. This isn’t my first visit and ..."
Reviewed on Sep 19, 2026
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.
Frequently asked questions
How much does a Headley vacation package cost?
You'll find cheap prices from CA $965 on Expedia for your Headley escape. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Headley costs.
What are the cheapest months to go to Headley?
You can usually find lower prices and greater availability in January, February and November. Check out our cheap Headley vacation packages and you could get some excellent off-season deals.
How many days is enough for Headley?
The ideal duration for your Headley vacation depends on what you'd like to do and see. Typically, a few days to a week will give you time to go to all the main attractions and explore some hidden gems along the way.
How to find the best Headley package deals?
Begin your search for a Headley package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Headley package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Headley escape underway.
Is it cheaper to book a Headley vacation as a package?
You can enjoy significant savings on your next Headley break by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to browse some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Headley?
Secure amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Headley escape.
How to plan a trip to Headley?
- Choose when to get away: Check your diary and pack your bags. Your favourite time of year and the activities on offer will also help you decide when to vacation in Headley.
- Figure out your budget: Ensure you have enough money to pay for everything from transportation and food to airfares and activities. Your hotel will likely be the biggest expense during your trip to Headley.
- Determine how many days away: Start by making a list of all the sights and activities you want to get to in Headley. Then, estimate how long you'll need for each, along with any travel time.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Headley vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
