Woolstone 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
Your Woolstone Vacation
Reserve a Woolstone vacation package and prepare to experience the best of this lively city. Consider staying in the neighborhood of Montpellier, which is great for bars and pubs, dining and cafes. Fill your days with visits to Cheltenham Racecourse, Sudeley Castle and Cheltenham Town Hall, some of the things you just have to see during a trip to Woolstone. No matter your travel plans or the size of your budget, organizing a tailored Woolstone vacation is easy with Expedia.
Top Woolstone Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ready to book your vacation to Woolstone?
Woolstone Hotel Deals
Queens Hotel Cheltenham
The Promenade Cheltenham England
Fully refundableReserve now, pay when you stay
CA $124
CA $149 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (1,019 reviews)
"Staff were lovely, receptionists very helpful, Sunday lunch was good again restaurant staff helpful and polite our room and bathroom was very clean a few grubby marks on the carpets were a little off putting otherwise a good size room. Breakfast was a help yourself buffet which was well looked after ..."
Reviewed on Aug 25, 2026
Cheltenham Chase Hotel & Spa
Shurdington Road Cheltenham England
Fully refundableReserve now, pay when you stay
CA $114
CA $137 total
Sep 20 - Sep 21
includes taxes & fees
8.2/10 Very good! (1,017 reviews)
"Lovely clean rooms, good breakfast with Jack working well around restaurant. Tony behind the bar was"
Reviewed on Aug 24, 2026
Gloucester Robinswood Hotel by Sunday
Marlstone Close Gloucester England
Fully refundableReserve now, pay when you stay
CA $83
CA $100 total
Sep 20 - Sep 21
includes taxes & fees
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.
What to do in Woolstone
Churchill War Rooms & Blenheim Palace Day Trip from London
CA $133
per adult
80% of travellers recommend
Oxford and Traditional Cotswolds Villages from London
CA $186
per adult
100% of travellers recommend
Cotswolds in a Day Tour from Moreton-in-Marsh / Stratford-on-Avon
CA $178
per adult
98% of travellers recommend
Frequently asked questions
How much does a Woolstone vacation package cost?
The cheapest Woolstone vacation package is CA $1,935, so your dream getaway can become a reality — without spending a fortune. Bundle flights, hotels, car rentals and more to custom build a package that's perfect for you.
How do I get a cheap travel package to Woolstone?
Crafting your own Woolstone vacation package with Expedia is an easy way to save. We offer access to over 550 airlines and 1,000,000 properties worldwide. With such an awesome range to select from, you'll have no issues putting together your dream getaway.
Where should I stay in Woolstone?
A vacation in Woolstone isn't complete without visiting Prescott Speed Hill Climb. Why not stay close to this popular attraction?
How far in advance should I book my Woolstone vacation?
Reserving your seat early with Expedia means one less thing to worry about. Most air carriers advertise tickets up to a year in advance. This is usually the cheapest time to book. If circumstances have left you booking late, discount flights to Woolstone sometimes occur a few weeks before departure.
What does an Expedia Woolstone travel package include?
It comes down to what you want. If you're traveling alone, you might decide to combine flights and hotels. Bringing the whole family to Woolstone? A travel package that includes flights, hotels and rental cars might be a better fit. Expedia gives you the flexibility and freedom to tailor your travel package.
What should I know before booking a Woolstone travel package?
Whether it's relaxation or adventure you're seeking, a Woolstone vacation package lets you organize your escape your way. Plus, you'll score great discounts just for combining your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Woolstone Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You're the boss! We have access to more than 550 partner airlines all over the world, so you have lots of choice when organizing your Woolstone trip.
If I'm not able to travel, can I cancel my Woolstone vacation package?
It's impossible to predict what tomorrow might bring, so it's good to know that you can change or cancel your Woolstone vacation package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
