Woolstone Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.
Belvilla at Brackley, near Silverstone Circuit

Belvilla at Brackley, near Silverstone Circuit

3 out of 5
Price was CA $990, price is now CA $915 per person
CA $915
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Birmingham (BHX)
7.4/10 Good! (42 reviews)
Great Hotel, ideally suited for my needs, travelled for work / business. Nice room, easy to park at Hotel. Food lovely and friendly staff. Very happy to stay here again.

Reviewed on Oct 16, 2026

Cosy Home Near Station, Parking, Netflix, Sleeps 5

Cosy Home Near Station, Parking, Netflix, Sleeps 5

4 out of 5
Price was CA $1,460, price is now CA $1,325 per person
CA $1,325
per person
Nov 28 - Dec 2
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Birmingham (BHX)
10/10 Exceptional! (2 reviews)
Excellent room and service

Reviewed on Sep 2, 2026

Windmill Village Hotel, Golf Club & Spa, BW Signature Collection

Windmill Village Hotel, Golf Club & Spa, BW Signature Collection

4 out of 5
Price was CA $1,546, price is now CA $1,406 per person
CA $1,406
per person
Nov 28 - Dec 2
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Birmingham (BHX)
8/10 Very good! (962 reviews)
We all had a good night sleep 👍good girls changing rooms👌and plenty of parking 🚘

Reviewed on Oct 26, 2026

Marston Farm Hotel

Marston Farm Hotel

3 out of 5
Price was CA $1,320, price is now CA $1,211 per person
CA $1,211
per person
Nov 28 - Dec 2
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Birmingham (BHX)
6.8/10 (321 reviews)
Having stayed in many hotels in the past this is the worst experience I have had. The reception staff were most unhelpful in fact very rude, made to feel as if we were inconveniencing him

Reviewed on Oct 26, 2026

Manor Hotel Solihull, BW Signature Collection

Manor Hotel Solihull, BW Signature Collection

4 out of 5
Meriden
Price was CA $1,595, price is now CA $1,471 per person
CA $1,471
per person
Nov 27 - Dec 2
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Birmingham (BHX)
8.6/10 Excellent! (1,006 reviews)

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Woolstone Hotel Deals

Cheltenham Chase Hotel & Spa

Cheltenham Chase Hotel & Spa

4 out of 5
Shurdington Road Cheltenham England
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Nov 26 to Nov 27
CA $135
CA $162 total
Nov 26 - Nov 27
includes taxes & fees
8.2/10 Very good! (1,007 reviews)
"Staff where excellent,room very nice breakfast very good overall an excellent stay."

Reviewed on Oct 26, 2026

Cheltenham Chase Hotel & Spa
Leonardo Hotel Cheltenham

Leonardo Hotel Cheltenham

4 out of 5
Gloucester Road Cheltenham England
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Nov 22 to Nov 23
CA $119
CA $143 total
Nov 22 - Nov 23
includes taxes & fees
8.4/10 Very good! (1,008 reviews)
"."

Reviewed on Oct 25, 2026

Leonardo Hotel Cheltenham
Queens Hotel Cheltenham

Queens Hotel Cheltenham

4 out of 5
The Promenade Cheltenham England
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Oct 29 to Oct 30
CA $139
CA $167 total
Oct 29 - Oct 30
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Beautiful hotel, excellent breakfast. Would have given five stars if there had not have been an issue where I was charged £56 parking for my one night stay, I questioned my bill to be told it’s a parking charge. I then asked how long do I get to stay, another lady said the charge was £17 and I was ..."

Reviewed on Oct 25, 2026

Queens Hotel Cheltenham
See all 3,484 properties in Woolstone
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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What to do in Woolstone

Cotswolds Full-Day Tour From Birmingham

Cotswolds Full-Day Tour From Birmingham

CA $151
per adult
100% of travellers recommend
Cotswolds Full-Day Tour From Birmingham
Cotswolds in a Day Tour from Moreton-in-Marsh / Stratford-on-Avon

Cotswolds in a Day Tour from Moreton-in-Marsh / Stratford-on-Avon

CA $160
per adult
96% of travellers recommend
Cotswolds in a Day Tour from Moreton-in-Marsh / Stratford-on-Avon
Oxford and Traditional Cotswolds Villages from London

Oxford and Traditional Cotswolds Villages from London

CA $187
per adult
98% of travellers recommend
Oxford and Traditional Cotswolds Villages from London
See all activities in Woolstone

Frequently asked questions

How much does a Woolstone vacation package cost?
The cheapest Woolstone vacation package is CA $915, 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.