Winterslow Vacations from $1,363

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Your Winterslow Vacation

The best way to experience this vibrant city is with a custom-made Winterslow vacation package. Base yourself in the neighborhood of Cholderton, which is good for history, nature and families or choose someplace else — our packages are all about you. A trip to Winterslow is a terrific opportunity to take in the sights. Check out renowned attractions like Salisbury Cathedral, Old Sarum and Salisbury Museum. No matter your travel plans or budget, organizing your ultimate tailored Winterslow vacation is easy with Expedia.

The Latest Winterslow vacation packages

Price found within the past 48 hours. Click for updated prices.
Leigh Park Country House Hotel & Vineyard, BW Signature Collection

Leigh Park Country House Hotel & Vineyard, BW Signature Collection

3 out of 5
Price was $1,506, price is now $1,363 per person
$1,363
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
8.2/10 Very Good! (636 reviews)
Great room and loved the vibe and atmosphere!

Reviewed on Nov 3, 2026

The Old Bell Hotel

The Old Bell Hotel

4 out of 5
Price was $2,157, price is now $1,854 per person
$1,854
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
9.4/10 Exceptional! (327 reviews)

The School Rooms Estate

The School Rooms Estate

4 out of 5
Price was $2,586, price is now $2,264 per person
$2,264
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
No reviews

Lucknam Park, Emblems Collection

Lucknam Park, Emblems Collection

5 out of 5
Price was $3,320, price is now $2,974 per person
$2,974
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
9.6/10 Exceptional! (217 reviews)

The New School Rooms

The New School Rooms

3.5 out of 5
Price was $1,682, price is now $1,512 per person
$1,512
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
No reviews

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What to do in Winterslow

Half Day Afternoon Stonehenge Tour from London with Admission

Half Day Afternoon Stonehenge Tour from London with Admission

$88
per adult
Half Day Afternoon Stonehenge Tour from London with Admission
Half-Day Small-Group Tour to Stonehenge from Bath

Half-Day Small-Group Tour to Stonehenge from Bath, inc Entry

$100
per adult
100% of travellers recommend
Half-Day Small-Group Tour to Stonehenge from Bath, inc Entry
Stonehenge Admission Ticket

Stonehenge Admission Ticket

$36
per adult
Stonehenge Admission Ticket
See all activities in Winterslow

Winterslow Hotel Deals

Leonardo Hotel Southampton

Leonardo Hotel Southampton

4 out of 5
1 Charlotte Place Southampton England
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $72 total per night from Nov 15 to Nov 16
$72 total
Nov 15 - Nov 16
Total with taxes and fees
Leonardo Hotel Southampton
Leonardo Royal Southampton Grand Harbour

Leonardo Royal Southampton Grand Harbour

4 out of 5
West Quay Road Southampton England
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $107 total per night from Nov 15 to Nov 16
$107 total
Nov 15 - Nov 16
Total with taxes and fees
8.6/10 Excellent! (1,734 reviews)
"Excellent desk staff. Shout out to Jimmy who was especially helpful. Great location, convenient parking. Would stay again."

Reviewed on Nov 8, 2026

Leonardo Royal Southampton Grand Harbour
Moxy Southampton

Moxy Southampton

3 out of 5
Harbour Parade Southampton England
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $88 total per night from Nov 22 to Nov 23
$88 total
Nov 22 - Nov 23
Total with taxes and fees
9/10 Wonderful! (1,083 reviews)
"Room was great except too hot Breakfast was very good Great location as we were going on a cruise"

Reviewed on Nov 9, 2026

Moxy Southampton
See all 1,632 properties in Winterslow
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 Winterslow Vacation Packages

Winterslow Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Southampton Airport (SOU)
Top Sights
Salisbury Cathedral, Cathedral Close and Salisbury Museum

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Frequently asked questions

How much does a Winterslow vacation package cost?
You can pick up a vacation package to this destination from $1,363 on Expedia. However, how much your vacation to Winterslow costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winterslow?
December, January and February are great times to look for cheap Winterslow vacation packages. Choosing to travel in quieter months means you can generally find lower prices on flights and accommodations.
How many days is enough for Winterslow?
The ideal duration of your Winterslow vacation depends on what you'd like to see. Usually, a handful of days to a week will give you plenty of time to check out all the top attractions and explore some hidden spots along the way.
How to find the best Winterslow package deals?
Finding a cheap Winterslow package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Winterslow package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Winterslow vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels separately. Better still, you can tailor your Winterslow getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Winterslow?
If you've got your Winterslow vacation dates confirmed, book as early as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Winterslow vacation packages?
Set off on your dream getaway to Winterslow with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait until the next payday — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stick to your budget and snap up travel deals before they disappear.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.