Woolstone Vacations from $678

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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.

The Latest Woolstone vacation packages

Price found within the past 48 hours. Click for updated prices.
The Olde Bell, BW Signature Collection

The Olde Bell, BW Signature Collection

3 out of 5
Price was $847, price is now $678 per person
$678
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
New York (JFK) to Birmingham (BHX)
8.2/10 Very Good! (407 reviews)
My go to place when I need to stay overnight in the area. Much better than staying at a hotel chain. This is an authentic English pub at its best. Had a great chat with the locals over a pint who are friendly. The breakfast was amazing. I would recommend thoroughly.

Reviewed on Dec 4, 2025

The President

The President

4 out of 5
Birmingham City Centre
Price was $1,323, price is now $821 per person
$821
per person
Jan 15 - Jan 20
found 6 hours ago
Roundtrip non-stop flight included
New York (JFK) to Birmingham (BHX)
8.8/10 Excellent! (13 reviews)
Nice communications from the property and good location. Nice clean property, we enjoyed out stay here.

Reviewed on May 25, 2023

Delta Hotels by Marriott Birmingham

Delta Hotels by Marriott Birmingham

4 out of 5
Edgbaston
Price was $907, price is now $731 per person
$731
per person
Jan 15 - Jan 20
found 6 hours ago
Roundtrip non-stop flight included
New York (JFK) to Birmingham (BHX)
8.8/10 Excellent! (207 reviews)
Room was spotless, staff were so friendly and helpful. Had an incredible stay!

Reviewed on Dec 6, 2025

OYO Tamworth Arms Boutique Pub & Hotel

OYO Tamworth Arms Boutique Pub & Hotel

4 out of 5
Price was $993, price is now $804 per person
$804
per person
Jan 15 - Jan 20
found 6 hours ago
Roundtrip non-stop flight included
New York (JFK) to Birmingham (BHX)
8.8/10 Excellent! (198 reviews)
Didn't have breakfast but room great staff exellent would stay again.

Reviewed on Nov 11, 2025

The Grand Hotel Birmingham

The Grand Hotel Birmingham

4 out of 5
Birmingham City Centre
Price was $1,231, price is now $1,008 per person
$1,008
per person
Jan 15 - Jan 20
found 6 hours ago
Roundtrip non-stop flight included
New York (JFK) to Birmingham (BHX)
9.4/10 Exceptional! (1,077 reviews)
Staff attention to detail in the bar and at breakfast could of helped better the experience

Reviewed on Dec 5, 2025

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Discover the most popular places to visit in Woolstone

Cheltenham Town Hall

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
Sudeley Castle featuring heritage architecture, a church or cathedral and a garden

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
Chedworth Roman Villa which includes heritage elements, a house and a park

Chedworth Roman Villa

Roman-British history comes to life at the bathhouses, mosaics and museum of this ancient villa set in the picturesque Cotswold countryside.

Chedworth Roman Villa

What to do in Woolstone

Cotswolds Full-Day Tour From Birmingham

Cotswolds Full-Day Tour From Birmingham

$105
per adult
100% of travellers recommend
Cotswolds Full-Day Tour From Birmingham
Travel the back roads in one of our comfy 16-seater Mercedes minibuses - we can go where big coaches can't!

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

$95
per adult
Secret Cotswolds Tour from Stratford-on-Avon or Moreton-in-Marsh
Cotswold London Full Day Tour

Cotswold London Full Day Tour

$99
per adult
Cotswold London Full Day Tour
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
$81 nightly
The price is $97 total per night from Jan 11 to Jan 12
$97 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Fabulous room, and service

Reviewed on Dec 4, 2025

Cheltenham Chase Hotel & Spa
Kings Head

Kings Head

4 out of 5
24 Market Place Cirencester England
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $119 total per night from Dec 22 to Dec 23
$119 total
Dec 22 - Dec 23
Total with taxes and fees
8.8/10 Excellent! (711 reviews)
Friendly & informative receptionist. Clean room. Lovely bar & restaurant in a fantastic location!

Reviewed on Dec 7, 2025

Kings Head
Leonardo Hotel Cheltenham

Leonardo Hotel Cheltenham

4 out of 5
Gloucester Road Cheltenham England
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $95 total per night from Dec 21 to Dec 22
$95 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
Room was lovely. We paid for breakfast but then changed our mind and they reimbursed us easily for it. The pool was a bit disappointing since there were classes on so it was noisy but we still enjoyed the swim/ hot tub. Thank you.

Reviewed on Nov 27, 2025

Leonardo Hotel Cheltenham
See all 3,126 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

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Frequently asked questions

How much does a Woolstone vacation package cost?
You can pick up a vacation package to this popular destination from $678 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.