Winterslow Vacations from $1,223

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Photo by Graham Horn

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.
Bristol Grand Hotel By Sunday

Bristol Grand Hotel By Sunday

4 out of 5
Bristol City Centre
Price was $1,295, price is now $1,223 per person
$1,223
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
7.8/10 Good! (1,020 reviews)
Clean room amazing location onsite parking great bar and curtious staff would stay again

Reviewed on Nov 5, 2025

Adam Close

Adam Close

4 out of 5
Price was $4,168, price is now $3,276 per person
$3,276
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
No reviews
Stylish Family Home With Garden

Stylish Family Home With Garden

2 out of 5
Price was $2,779, price is now $2,520 per person
$2,520
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
No reviews
Thornbury Castle, Relais & Châteaux

Thornbury Castle, Relais & Châteaux

4 out of 5
Thornbury
Price was $1,518, price is now $1,400 per person
$1,400
per person
Dec 14 - Dec 16
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Bristol (BRS)
9.6/10 Exceptional! (599 reviews)
Hundreds of years after the second wealthiest man in Britain stops building thorrnbury castle because he gets beheaded by Henry 8th for gossiping about him there we were, in the sumptuous luxurious hotel, with the Michelin key, eating top notch scoff in the restaurant with 3 AA rosettes looking forward to a night in the tower.

Reviewed on Oct 26, 2025

The Hubert - Your Apartment

The Hubert - Your Apartment

4.5 out of 5
Saint Paul's
Price was $1,509, price is now $1,418 per person
$1,418
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
No reviews
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Discover the most popular places to visit in Winterslow

Stonehenge showing heritage elements

Stonehenge

This powerful prehistoric structure is one of England’s most visited monuments and an important UNESCO World Heritage Site.

Stonehenge
Salisbury Cathedral featuring religious aspects and a church or cathedral

Salisbury Cathedral

Climb to the top of the country’s tallest spire and check the time on the hands of a 14th-century clock.

Salisbury Cathedral
Old Sarum featuring a ruin and heritage elements

Old Sarum

Climb to the top of this Iron Age hilltop monument and cross the wooden bridge to see a castle built by William the Conqueror.

Old Sarum

What to do in Winterslow

Windsor Castle, Stonehenge & Bath Full-Day Tour

Windsor Castle, Stonehenge & Bath Day Tour with Expert Guide

$119
per adult
88% of travellers recommend
Windsor Castle, Stonehenge & Bath Day Tour with Expert Guide
stone structures at Stonehenge in England

Stonehenge and Bath Tour with Roman Baths

$101
per adult
76% of travellers recommend
Stonehenge and Bath Tour with Roman Baths
From Birmingham Stonehenge and Bath Day Tour

From Birmingham Stonehenge and Bath Day Tour

$107
per adult
From Birmingham Stonehenge and Bath Day Tour
See all activities in Winterslow

Winterslow Hotel Deals

The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane, Winchester, England
Fully refundableReserve now, pay when you stay
$141 nightly
The price is $169 total per night from Nov 19 to Nov 20
$169 total
Nov 19 - Nov 20
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
Very good hotel. All very clean. Didn’t get my drinks vouchers which was disappointing.

Reviewed on Nov 1, 2025

The Winchester Hotel & Spa
Moxy Southampton

Moxy Southampton

3 out of 5
Harbour Parade, Southampton, England
Fully refundableReserve now, pay when you stay
$64 nightly
The price is $77 total per night from Nov 16 to Nov 17
$77 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (1,019 reviews)
No

Reviewed on Nov 3, 2025

Moxy Southampton
Leonardo Hotel Southampton

Leonardo Hotel Southampton

4 out of 5
1 Charlotte Place, Southampton, England
Fully refundable
$69 nightly
The price is $82 total per night from Nov 14 to Nov 15
$82 total
Nov 14 - Nov 15
Total with taxes and fees
8.4/10 Very Good! (1,215 reviews)
clean room and friendly staff. Central location and quiet. Good breakfast selection

Reviewed on Nov 3, 2025

Leonardo Hotel Southampton
See all 1,508 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 $1,223 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.