Kingston Vacations from $738

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Your Kingston Vacation

Reserve a Kingston vacation package and get set to experience the best of this city. Consider basing yourself in the neighborhood of Wroxall, which is good for culture, history and walking. Make your trip to Kingston even more enjoyable by including some sightseeing. Ventnor Beach, Ventnor Botanic Garden and Blackgang Chine are some of the popular attractions you'll want to explore. Expedia has what you need to escape your daily routine. Tailor your vacation to Kingston to match your travel style, whatever that may be!

The Latest Kingston vacation packages

Price found within the past 48 hours. Click for updated prices.
Warbrook House Heritage Hotel

Warbrook House Heritage Hotel

4 out of 5
Price was $836, price is now $738 per person
$738
per person
Feb 13 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Southampton (SOU)
7.6/10 Good! (796 reviews)
everything was lovely, except toilet had continous small flow from cistern which was a little noisy. I reported it

Reviewed on Dec 13, 2025

Old Thorns Hotel & Resort

Old Thorns Hotel & Resort

4 out of 5
Price was $1,758, price is now $1,532 per person
$1,532
per person
Mar 3 - Mar 7
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Southampton (SOU)
8.4/10 Very Good! (1,000 reviews)
Clean, well presented hotel, staff helpful and breakfast good

Reviewed on Dec 10, 2025

Audleys Wood Hotel

Audleys Wood Hotel

4 out of 5
Price was $1,198, price is now $1,048 per person
$1,048
per person
Mar 3 - Mar 7
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Southampton (SOU)
9.2/10 Wonderful! (435 reviews)
Disappointed no coffee and tea facilities in the room room service food cold

Reviewed on Oct 8, 2025

Hotel du Vin & Bistro Winchester

Hotel du Vin & Bistro Winchester

4 out of 5
Price was $1,626, price is now $1,426 per person
$1,426
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Southampton (SOU)
9/10 Wonderful! (543 reviews)
A very pleasant two-night stay in a convenient location in Winchester. Good value for money given its premium look and feel. My only concern was confusion over the way my credit card was loaded on check-in with the full cost of the booking + another almost full day.

Reviewed on Dec 5, 2025

The Cricketers Inn

The Cricketers Inn

3 out of 5
Price was $1,276, price is now $1,129 per person
$1,129
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Southampton (SOU)
9.6/10 Exceptional! (25 reviews)
The dinners and breakfasts were wonderful and the inn hosts were amazing.

Reviewed on Sep 25, 2025

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Discover the most popular places to visit in Kingston

Ventnor Beach, Isle of Wight.

Ventnor Beach

If a restful vacation is part of your travel plans, Ventnor Beach might be the perfect place to seek out during your trip to Ventnor. Wander the gardens and seaside in this quaint area.

Ventnor Beach
Beautiful lighthouse, well worth steep climb

St. Catherine's Lighthouse

You can find out about the history of Niton and Whitwell with a stop at St. Catherine's Lighthouse. Wander the beautiful beaches and seaside in the area.

St. Catherine's Lighthouse
Visiting the donkey sanctuary in Ventnor, lots of chatter between the donkeys 😂❤️

Isle of Wight Donkey Sanctuary

See the exotic and native animals who live at Isle of Wight Donkey Sanctuary during your travels in Wroxall. Wander the area's beautiful beaches or simply enjoy one of its lively bars.

Isle of Wight Donkey Sanctuary

What to do in Kingston

The rear of the House - but the front as you come from the sea

Osborne House-A driver guided tour of Victoria's Island Paradise

$1,024
per traveler
Osborne House-A driver guided tour of Victoria's Island Paradise
See all activities in Kingston

Kingston Hotel Deals

Holiday Inn Portsmouth by IHG

Holiday Inn Portsmouth by IHG

4 out of 5
Pembroke Road Portsmouth England
Fully refundable
$61 nightly
The price is $74 total per night from Jan 4 to Jan 5
$74 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
Bar service could have been a little quicker/better organised. Otherwise all good

Reviewed on Dec 9, 2025

Holiday Inn Portsmouth by IHG
Harbour Hotel Southampton

Harbour Hotel Southampton

5 out of 5
5 Maritime Walk Southampton England
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $221 total per night from Dec 29 to Dec 30
$221 total
Dec 29 - Dec 30
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
Lovely room and spa and nice staff.

Reviewed on Dec 4, 2025

Harbour Hotel Southampton
Village Hotel Portsmouth

Village Hotel Portsmouth

4 out of 5
Lakeshore Drive Portsmouth England
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $86 total per night from Dec 28 to Dec 29
$86 total
Dec 28 - Dec 29
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Really friendly and helpful staff. Room clean and roomy. Free parking at weekends. Food in restaurant good. Starbucks in lobby if you don't want to pay for breakfast. Pay a fee to access pool and gym. Would stay again.

Reviewed on Dec 8, 2025

Village Hotel Portsmouth
See all 2,657 properties in Kingston
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 Kingston Vacation Packages

Kingston Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Southampton Airport (SOU)
Top Sights
Ventnor Beach, Blackgang Chine and Isle of Wight Donkey Sanctuary

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Frequently asked questions

How much does a Kingston vacation package cost?
You'll find cheap prices from $738 on Expedia for your Kingston escape. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Kingston costs.
What are the cheapest months to go to Kingston?
April, July and December are the best times to look for cheap Kingston vacation packages. Choosing to travel in quieter months means you can usually find lower prices on accommodations and flights.
How many days is enough for Kingston?
The ideal length for your Kingston vacation depends on what you'd like to do and see. Generally, a few days to a week will give you plenty of time to go to all the leading attractions and explore some hidden treasures along the way.
How to find the best Kingston package deals?
Use Expedia's handy filters to find some terrific Kingston package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Kingston package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Kingston vacation as a package?
You can enjoy significant savings on your next Kingston break by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to view some great hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Kingston?
If you have your Kingston vacation dates confirmed, book as early as you can to snap up some outstanding deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for impromptu escapes.
Does Expedia offer Book Now, Pay Later Kingston vacation packages?
If you're anything like us, you love traveling the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Kingston trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.