Woolstone Vacations from $580

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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.
Dancenter Birmingham Airport Near Nec

Dancenter Birmingham Airport Near Nec

3 out of 5
Price was $668, price is now $580 per person
$580
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
New York (NYC) to Birmingham (BHX)
6.6/10 (17 reviews)
Good experience, only issue was that the room was too hot as radiators stayed on even though on off position but otherwise good location.

Reviewed on Apr 27, 2025

Cosy Home Near Station, Parking, Netflix, Sleeps 5

Cosy Home Near Station, Parking, Netflix, Sleeps 5

4 out of 5
Price was $1,223, price is now $953 per person
$953
per person
Dec 3 - Dec 9
found 22 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Birmingham (BHX)
No reviews
Really good property to book out. Good communication with owners when needed

Reviewed on Sep 7, 2025

Cozy Cotswolds Retreat in Dursley

Cozy Cotswolds Retreat in Dursley

2 out of 5
Price was $837, price is now $707 per person
$707
per person
Oct 11 - Oct 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Birmingham (BHX)
10/10 Exceptional! (1 review)
KCS Luxury Apartment - Broad Street Birmingham

KCS Luxury Apartment - Broad Street Birmingham

3.5 out of 5
Birmingham City Centre
Price was $807, price is now $706 per person
$706
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
New York (NYC) to Birmingham (BHX)
9.2/10 Wonderful! (23 reviews)
Great city centre property with a 5 minute walk to bars and restaurants. Really quiet also considering the location.

Reviewed on Nov 24, 2024

Stunning 1BR Apt in Central Cheltenham

Stunning 1BR Apt in Central Cheltenham

2 out of 5
Price was $752, price is now $658 per person
$658
per person
Oct 11 - Oct 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Birmingham (BHX)
No reviews
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Discover the most popular places to visit in Woolstone

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

Sudeley Castle

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
Cheltenham Town Hall

Cheltenham Town Hall

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 top-notch restaurants.

Cheltenham Town Hall
The Model Village which includes interior views

The Model Village

Walk amid a scale model replica of the shops, houses and historic landmarks that were present in Bourton-on-the-Water during the 1930s.

The Model Village

What to do in Woolstone

Classic Cotswolds – Online Self-Guided Road Trip Plan

Classic Cotswolds – Online Self-Guided Road Trip Plan

$18
per traveler
Classic Cotswolds – Online Self-Guided Road Trip Plan
Blenheim Palace and Cotswolds Private Tour

Blenheim Palace and Cotswolds Private Tour

$1,067
per traveler
Blenheim Palace and Cotswolds Private Tour
Private Full Day Tour to Cotswolds from London

Private Full Day Tour to Cotswolds from London

$3,322
per adult
Private Full Day Tour to Cotswolds from London
See all activities in Woolstone

Woolstone Hotel Deals

Cheltenham Chase Hotel & Spa

Cheltenham Chase Hotel & Spa

4 out of 5
Shurdington Road, Brockworth, Cheltenham, England
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $104 total per night from Sep 28 to Sep 29
$104 total
Sep 28 - Sep 29
Total with taxes and fees
Cheltenham Chase Hotel & Spa
Kings Head Hotel

Kings Head Hotel

4 out of 5
24 Market Place, Cirencester, England
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $160 total per night from Sep 14 to Sep 15
$160 total
Sep 14 - Sep 15
Total with taxes and fees
Kings Head Hotel
Holiday Inn Gloucester-Cheltenham by IHG

Holiday Inn Gloucester-Cheltenham by IHG

4 out of 5
Crestway, Barnwood, Gloucester, England
Fully refundable
$83 nightly
The price is $100 total per night from Sep 21 to Sep 22
$100 total
Sep 21 - Sep 22
Total with taxes and fees
Holiday Inn Gloucester-Cheltenham by IHG
See all 3,030 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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Frequently asked questions

How much does a Woolstone vacation package cost?
You can pick up a vacation package to this popular destination from $580 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.