Benenden Vacations from $792

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Your Benenden Vacation

Lock in a Benenden vacation package that includes everything you need and no unnecessary extras. Great for nature, views and walking, think about staying in the neighborhood of Winchelsea. Every trip to Benenden needs a well-crafted itinerary. Fill yours with big-name attractions like Sissinghurst Castle and Garden, Bedgebury National Pinetum and Forest and Cranbrook Museum. No matter your travel plans or budget, organizing your ultimate tailored Benenden vacation is a cinch with Expedia.

The Latest Benenden vacation packages

Price found within the past 48 hours. Click for updated prices.
Woodcock Inn

Woodcock Inn

3 out of 5
Price was $859, price is now $792 per person
$792
per person
Apr 1 - Apr 6
found 14 hours ago
Roundtrip flight included
New York (JFK) to London (LGW)
8.2/10 Very Good! (59 reviews)
Very attentive staff

Reviewed on Nov 15, 2025

Nutfield Priory Hotel And Spa

Nutfield Priory Hotel And Spa

4 out of 5
Price was $1,234, price is now $1,118 per person
$1,118
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
New York (NYC) to London (LGW)
8.8/10 Excellent! (398 reviews)
lovely stay will defo revisit

Reviewed on Jan 3, 2026

Ashdown Park Hotel & Country Club

Ashdown Park Hotel & Country Club

4 out of 5
Price was $1,274, price is now $1,161 per person
$1,161
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
New York (NYC) to London (LGW)
8.8/10 Excellent! (540 reviews)
This hotel is the goal standard. Management from other hotels should come and visit it. From beginning to end the service engagement with well informed and genuinely welcoming. It’s a very interesting historical setting. When they say they are dog friendly, they genuinely are.

Reviewed on Feb 2, 2026

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Discover the most popular places to visit in Benenden

One of the many gardens around the estate

Sissinghurst Castle and Garden

Sissinghurst Castle and Garden is just one of the places to see in Cranbrook, so why not enjoy the other things to explore during your travels? Check out the spas and top-notch restaurants in this quaint area.

Sissinghurst Castle and Garden

Bedgebury National Pinetum and Forest

Enjoy an outing to Bedgebury National Pinetum and Forest during your stay in Goudhurst. Amble within picturesque gardens or visit the spas in this relaxing area.

Bedgebury National Pinetum and Forest

Hole Park Gardens

Explore the great outdoors at Hole Park Gardens, a lovely green space in Rolvenden. Check out the spas and top-notch restaurants in this quaint area.

Hole Park Gardens

What to do in Benenden

Sussex Heritage Coast - Online Self Guided Road Trip Plan

Sussex Heritage Coast - Online Self Guided Road Trip Plan

$18
per traveler
Sussex Heritage Coast - Online Self Guided Road Trip Plan
See all activities in Benenden

Benenden Hotel Deals

ORIDA Maidstone Hotel

ORIDA Maidstone Hotel

3 out of 5
Bearsted Rd Maidstone England
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (1,238 reviews)
Room good size for family. Staff very helpful at check in. Breakfast good quality as well

Reviewed on Feb 14, 2026

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ORIDA Maidstone Hotel
Delta Hotels by Marriott Tudor Park Country Club

Delta Hotels by Marriott Tudor Park Country Club

4 out of 5
Ashford Road Maidstone England
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $115 total per night from Mar 8 to Mar 9
$115 total
Mar 8 - Mar 9
Total with taxes and fees
8.6/10 Excellent! (925 reviews)
Clean and spacious room. V good friendly staff.

Reviewed on Jan 27, 2026

Delta Hotels by Marriott Tudor Park Country Club
Ashford International Hotel & Spa

Ashford International Hotel & Spa

4 out of 5
Simone Weil Avenue Ashford England
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $104 total per night from Feb 22 to Feb 23
$104 total
Feb 22 - Feb 23
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
Staff seemed courteous. Rooms were to the expectations. The Sauna and Jacuzzi were not working which was a shame. But over, happy with our stay.

Reviewed on Feb 5, 2026

Ashford International Hotel & Spa
See all 2,286 properties in Benenden
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 Benenden Vacation Packages

Benenden Essential Information

Language
English
Currency
British pounds sterling
Population
790
Top Sights
Sissinghurst Castle and Garden, Cranbrook Museum and Morgan Museum

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Frequently asked questions

How much does a Benenden vacation package cost?
You'll find cheap prices from $792 on Expedia for your Benenden getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Benenden costs.
What are the cheapest months to go to Benenden?
You can typically find lower prices and better availability in July, November and December. Explore our cheap Benenden vacation packages and you could land some great off-season discounts.
How many days is enough for Benenden?
Usually, a handful of days is enough to see the major sights during your Benenden vacation. But if you'd like to have time to unwind or take day trips, consider extending your itinerary.
How to find the best Benenden package deals?
Start your search for a Benenden package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Benenden package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Benenden adventure underway.
Is it cheaper to book a Benenden vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still get the freedom to create a personalized Benenden vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Benenden?
If you've got your Benenden vacation dates confirmed, book as early as you can to grab some unbeatable deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Benenden vacation packages?
Set off on your dream getaway to Benenden with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until your next payday — we've teamed up with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.