Woolstone Vacations from $1,537

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, 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.

The Latest Woolstone vacation packages

Price found within the past 48 hours. Click for updated prices.
Nailcote Hall Hotel

Nailcote Hall Hotel

4 out of 5
Price was $1,651, price is now $1,537 per person
$1,537
per person
Jun 26 - Jun 29
found 6 hours ago
Roundtrip flight included
San Antonio (SAT) to Birmingham (BHX)
8.4/10 Very Good! (509 reviews)
Most impressed by: The Staff, they were lovely. Breakfast was delicious. Entertainment, Colin Mills was outstanding. The bedroom was bright, airy, clean and nicely laundered. Not so good: Lift didn't go to top floor where we stayed so we had lots to carry, which was quite difficult for our party. Bathroom was not as clean as it could have been.

Reviewed on Apr 22, 2026

The President

The President

4 out of 5
Birmingham City Centre
Price was $1,884, price is now $1,703 per person
$1,703
per person
Jun 26 - Jun 29
found 6 hours ago
Roundtrip flight included
San Antonio (SAT) to Birmingham (BHX)
8.6/10 Excellent! (15 reviews)
Excellent location for our stay. The apartment was clean and spacious and having secure parking was a bonus. Communication from the host was also excellent.

Reviewed on Dec 26, 2025

Domo Boutique Hotel Birmingham

Domo Boutique Hotel Birmingham

3 out of 5
Edgbaston
Price was $1,844, price is now $1,674 per person
$1,674
per person
Jun 26 - Jun 29
found 6 hours ago
Roundtrip flight included
San Antonio (SAT) to Birmingham (BHX)
10/10 Exceptional! (3 reviews)
The Class Place

The Class Place

4 out of 5
Birmingham City Centre
Price was $1,831, price is now $1,677 per person
$1,677
per person
Jun 26 - Jun 29
found 6 hours ago
Roundtrip flight included
San Antonio (SAT) to Birmingham (BHX)
8.8/10 Excellent! (18 reviews)
Great! Good location and great communication for checking in.

Reviewed on Feb 1, 2019

Pools Cottage - The Farmhouse

Pools Cottage - The Farmhouse

2 out of 5
Price was $3,733, price is now $3,444 per person
$3,444
per person
Jun 26 - Jun 29
found 6 hours ago
Roundtrip flight included
San Antonio (SAT) to Birmingham (BHX)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Woolstone
View all trips

Discover the most popular places to visit in Woolstone

F04AR9 Cheltenham Town Hall, Cheltenham, Gloucestershire, England

Cheltenham Town Hall

4/5(2 reviews)

Find out about the history of Cheltenham when you take a trip to Cheltenham Town Hall. Wander the area's picturesque gardens or simply enjoy one of its lively bars.

Cheltenham Town Hall
Cheltenham Racecourse from Cleeve Hill

Cheltenham Racecourse

3.5/5(3 reviews)

You can take time to visit Cheltenham Racecourse during your travels to Cheltenham. Discover the beautiful countryside and lively bars in this relaxing area.

Cheltenham Racecourse
Sudeley Castle

Sudeley Castle

4.5/5(2 reviews)

Uncover centuries of royal history amid the halls, gardens and art exhibitions of this 15th-century castle set in the shadow of the Cotswold Hills.

Sudeley Castle

What to do in Woolstone

Secret Cotswolds Tour from Stratford-on-Avon or Moreton-in-Marsh

Secret Cotswolds Tour from Stratford-on-Avon or Moreton-in-Marsh

$109
per adult
Secret Cotswolds Tour from Stratford-on-Avon or Moreton-in-Marsh
Full Day Cotswolds Guided Group Tour from London

Full Day Cotswolds Tour from London

$94
per adult
100% of travellers recommend
Full Day Cotswolds Tour from London
Cotswolds Full-Day Tour From Birmingham

Cotswolds Full-Day Tour From Birmingham

$109
per adult
100% of travellers recommend
Cotswolds Full-Day Tour From Birmingham
See all activities in Woolstone

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
$86 nightly
The price is $104 total per night from May 31 to Jun 1
$104 total
May 31 - Jun 1
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
Good place to get away. Spa facilities good and clean room

Reviewed on May 8, 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
$84 nightly
The price is $100 total per night from May 31 to Jun 1
$100 total
May 31 - Jun 1
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
The hotel is lovely and very convenient for Cheltenham x and the Spa is lovely

Reviewed on May 7, 2026

Leonardo Hotel Cheltenham
Hatherley Manor Hotel & Spa

Hatherley Manor Hotel & Spa

4 out of 5
Down Hatherley Lane Gloucester England
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $130 total per night from May 21 to May 22
$130 total
May 21 - May 22
Total with taxes and fees
8.4/10 Very Good! (802 reviews)
Ants in the bedroom and on the bed

Reviewed on May 3, 2026

Hatherley Manor Hotel & Spa
See all 3,246 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.

Find the Best Woolstone Vacation Packages

Woolstone Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Brize Norton (BZZ-RAF Brize Norton)
Top Sights
Sudeley Castle, Everyman Theatre and Cheltenham Playhouse

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Woolstone vacation package cost?
You can pick up a vacation package to this popular destination from $1,537 on Expedia. However, how much your vacation to Woolstone costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Woolstone?
You can generally find reduced prices and greater availability in November, December and January. Browse our cheap Woolstone vacation packages and you could score some great off-season discounts.
How many days is enough for Woolstone?
With a well-organized itinerary, you can easily tick off the top Woolstone attractions in a few days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Woolstone vacation for longer.
How to find the best Woolstone package deals?
Begin your search for a Woolstone package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Woolstone package deal right away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Woolstone escape off to a flying start.
Is it cheaper to book a Woolstone vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and accommodations individually. Better still, you can personalize your Woolstone getaway to fit your exact needs. Choose 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 Woolstone?
If you have your Woolstone travel dates finalized, book as early as you can to bag some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for traveling on a whim.
How to plan a trip to Woolstone?

  1. Choose when to travel: Check your schedule and get your bags packed. Your preferred time of year and the available activities will also help you decide when to escape to Woolstone.
  2. Set a budget: Consider costs such as food, flights and transportation when working out how much to save for your trip to Woolstone. Then, pick a property that matches your budget, whether that's an affordable option or a swankier getaway.
  3. Organize your Woolstone getaway with Expedia's trip planning tool: Look for and book stays and activities all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Woolstone together.
  4. Decide how long to go away for: Now that you're more familiar with Woolstone, you can figure out the right length of your vacation. Put together a draft itinerary and allocate enough time to cover everything you want to see.
  5. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Woolstone vacation package.
  6. Book activities and experiences ahead of time: Whether it's entrance to a major attraction or a day trip in nature, you won't have to worry about missing out on the highlights of Woolstone. Find all the fun things to do in Woolstone with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Woolstone vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Woolstone vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap 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.