Whippingham Vacations from $1,065

Book a Hotel + Flight or Car together to unlock savings

Photo by Terry Hicks

Your Whippingham Vacation

When a getaway to the city is calling, answer it with a vacation package to Whippingham. The neighborhood of Wroxall, which is good for culture, history and walking, makes an awesome base for your adventures. Fill up your itinerary with tours of Osborne House, St Mildreds Church and Classic Boat Museum, some of the things you just have to see during your trip to Whippingham. Whoever you're traveling with and whatever you want to spend, your dream Whippingham vacation is just a few clicks away with Expedia.

The Latest Whippingham vacation packages

Price found within the past 48 hours. Click for updated prices.
Winchester Wessex Hotel by Sunday

Winchester Wessex Hotel by Sunday

4 out of 5
Price was $1,150, price is now $1,065 per person
$1,065
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Miami (MIA) to Southampton (SOU)
7.4/10 Good! (1,008 reviews)
The room was tired and dark (very dark furniture) If someone wanted to use a computer or prepare some paperwork, the lighting was not adequate One of the lamps was not working so we had to ask for someone to replace the light bulb The staff on Reception were great and very helpful The parking situation was awful - too few spaces!

Reviewed on Oct 29, 2025

The Pilot Boat Inn

The Pilot Boat Inn

3.5 out of 5
Price was $2,152, price is now $1,832 per person
$1,832
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Southampton (SOU)
8.4/10 Very Good! (21 reviews)
The whole building was unique. unusual but very comfortable. We could have done with another chair in the Room.....but other than that fine. 'Mine host ' was very friendly and helpful. We had a bit of banter.

Reviewed on Jul 26, 2024

No.4 Carlton Hotel

No.4 Carlton Hotel

4 out of 5
The Polygon
Price was $2,470, price is now $2,132 per person
$2,132
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Southampton (SOU)
9.6/10 Exceptional! (122 reviews)
Decor, hotel quality, and cleanliness was excellent. Lots of great amenities included. Guest service was friendly and efficient. Important to note that there is no elevator. Also, glassed in bathroom was not very private and sound through ceiling and room door was very noticeable.

Reviewed on Oct 23, 2025

Hotel du Vin & Bistro Winchester

Hotel du Vin & Bistro Winchester

4 out of 5
Price was $2,476, price is now $2,249 per person
$2,249
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Southampton (SOU)
9/10 Wonderful! (536 reviews)
Lovely hotel and helpful staff, We were given an upgrade so our room was near our daughters Breakfast excellent snd parking great

Reviewed on Oct 24, 2025

Winchester Royal Hotel

Winchester Royal Hotel

4 out of 5
Price was $2,038, price is now $1,852 per person
$1,852
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Southampton (SOU)
8.4/10 Very Good! (1,004 reviews)
Clean room. Helpful and friendly staff. Good amenities at hotel. Great central location.

Reviewed on Oct 29, 2025

Don't see what you're looking for?
See all available trips from Columbus to Whippingham
View all trips

Discover the most popular places to visit in Whippingham

Exstensive gardens of the estate of Osborne House near Cowes on the Isle of Wight. . Summer residence of the late Queen Victoria now maintained for the national by English Heritage. A great visit. House and Garden will be a full day.

Osborne House

5/5(7 reviews)

Find out about the history of East Cowes when you take a trip to Osborne House. Stroll along the area's seaside, or simply savor its lively bars.

Osborne House

East Cowes Ferry Terminal

Explore the waterfront in East Cowes with a trip to East Cowes Ferry Terminal. Stroll along the area's beautiful beaches, or simply savor its lively bars.

East Cowes Ferry Terminal

Classic Boat Museum

You can study the exhibits at Classic Boat Museum, a museum with a story of its own, during your trip to East Cowes. Stroll along the area's beautiful beaches, or simply savor its top-notch restaurants.

Classic Boat Museum

What to do in Whippingham

Picture 2 for Activity Portsmouth: Historic Dockyard Ultimate Explorer Ticket

Portsmouth: Historic Dockyard Ultimate Explorer Ticket

$61
per adult
76% of travellers recommend
Portsmouth: Historic Dockyard Ultimate Explorer Ticket
Portsmouth: Old Portsmouth Historical Walking Tour

Portsmouth: Old Portsmouth Historical Walking Tour

$13
per adult
Portsmouth: Old Portsmouth Historical Walking Tour
Bar & Club queue jump entry Party Pass to multiple venues in Portsmouth

Bar & Club queue jump entry Party Pass to multiple venues in Portsmouth

$13
per adult
Bar & Club queue jump entry Party Pass to multiple venues in Portsmouth
See all activities in Whippingham

Whippingham Hotel Deals

Moxy Southampton

Moxy Southampton

3 out of 5
Harbour Parade, Southampton, England
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $78 total per night from Nov 16 to Nov 17
$78 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 refundableReserve now, pay when you stay
$69 nightly
The price is $83 total per night from Nov 9 to Nov 10
$83 total
Nov 9 - Nov 10
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
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
$88 nightly
The price is $105 total per night from Nov 9 to Nov 10
$105 total
Nov 9 - Nov 10
Total with taxes and fees
8.6/10 Excellent! (1,666 reviews)
Breakfast and parking included. I had forgotten my cruise boarding passes and cruise parking certificate. Magdalena on reception was brilliant in getting copies printed from my email.

Reviewed on Nov 2, 2025

Leonardo Royal Southampton Grand Harbour
See all 4,045 properties in Whippingham
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 Whippingham Vacation Packages

Whippingham Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Southampton Airport (SOU)
Top Sights
Osborne House, St Mildreds Church and Classic Boat Museum

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 Whippingham vacation package cost?
You'll find cheap prices from $1,065 on Expedia for your Whippingham getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Whippingham costs.
What are the cheapest months to go to Whippingham?
January, September and December are the best times to look for cheap Whippingham vacation packages. Traveling in less busy months means you can generally find lower prices on flights and accommodations.
How many days is enough for Whippingham?
The ideal length of your Whippingham vacation depends on what you'd like to see. Typically, a handful of days to a week will give you time to visit all the top sights and explore some hidden treasures along the way.
How to find the best Whippingham package deals?
Use Expedia's handy filters to help you find some terrific Whippingham package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Whippingham package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Whippingham vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking stays and flights separately. Better still, you can personalize your Whippingham getaway to match your exact style. 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 Whippingham?
Secure incredible discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Whippingham vacation.
Does Expedia offer Book Now, Pay Later Whippingham vacation packages?
Your Whippingham getaway is meant to be an escape from your busy life, not a source of money worries. So to allow you more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.