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Benenden Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Benenden vacation rentals

A cobblestone street lined with traditional buildings, some with ivy and flower boxes, and street lamps.

1. Mafeking by inspirestays-com - a cottage that sleeps 6 guests in 3 bedrooms

Mafeking by inspirestays-com - a cottage that sleeps 6 guests in 3 bedrooms
Benenden
9.8 out of 10, Exceptional, (21 reviews)
"A wonderful place for a holiday Nice location. Good opportunity for excursions to Hastings, Tenterden, Bodiam. Stop off at The Bull or the Milkhouse in Sissinghurst."
United States
Hartmut K.
$990 nightly
The price is $990
Nov 21 - Nov 22
Total with taxes and fees
Mafeking by inspirestays-com - a cottage that sleeps 6 guests in 3 bedrooms
An open door leading to a wooden deck with a view of a green landscape and trees.

2. Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom

Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
Tenterden
9.6 out of 10, Exceptional, (14 reviews)
"Amazing break away, beautiful holiday home and lovely area "
United Kingdom
Dean
$273 nightly
The price is $273
Nov 23 - Nov 24
Total with taxes and fees
Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
A restaurant interior with wooden tables and chairs, a bar area with a bartender, and a brick wall with framed pictures.

3. Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom

Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom
Tenterden
9.2 out of 10, Wonderful, (5 reviews)
"Has everything you need. Very clean and comfortable. Only problem was the light coming in early in the morning, may want to take a sleep mask with you if you’re a light sleeper. Other thank that could not fault it."
United States
Rebecca J.
$299 nightly
The price is $299
Nov 23 - Nov 24
Total with taxes and fees
Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom
A wooden cabin with a hot tub, a covered deck, and a sign reading "Cascade."

4. Cascade - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom

Cascade - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
Tenterden
9.8 out of 10, Exceptional, (7 reviews)
"Found this place fairly last minute and couldn’t believe what a little gem it was. Gorgeous surroundings, an oasis of calm. We had a lovely stay."
United States
Anonymous traveler
$273 nightly
The price is $273
Nov 23 - Nov 24
Total with taxes and fees
Cascade - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
A wooden deck with a wooden chair and table, a blanket, and breakfast items.

5. Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom

Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
Tenterden
9.0 out of 10, Wonderful, (6 reviews)
"Great little property, surprisingly comfortable for a small space, nice rural views from the lovely hot tub, and great beer from the onsite brewery!"
United States
Harry I.
$273 nightly
The price is $273
Nov 23 - Nov 24
Total with taxes and fees
Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
A modern bedroom with a large bed, a sitting area with a chair, and a view of the garden through a glass door.

6. The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom

The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom
Rye
9.0 out of 10, Wonderful, (6 reviews)
"Beautiful accommodation, with lovely vaulted ceiling making it bright and airy High quality finishes all round Kitchen has everything you need and a bottle of milk waiting in the fridge was a lovely touch Tea bags, coffee pods, crisps and biscuits also provided Bed was comfortable and high quality bedding Lovely big fluffy towels and M&S toiletries provided. It was so quiet at night meaning a great night sleep A lovely stay and would recommend a trip to Caster sands and Rye center"
United States
Lynn B.
$258 nightly
The price is $258
Nov 7 - Nov 8
Total with taxes and fees
The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom
A greenhouse structure surrounded by yellow flowering plants.

7. A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye

A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye
Rye
10.0 out of 10, Exceptional, (2 reviews)
"A little gem nestled in the countryside with glorious views. Lucy’s apartment was spotlessly clean and tidy, comfortable and very well equipped. Lucy is an absolute hoot- very welcoming and full of suggestions of things to see or do. Perfect for dogs too, with a lovely enclosed garden and lots of walks from the location detailed in the information folder. Lots of lovely pubs nearby too including a local just across the way. We would definitely come back."
United Kingdom
Kerry H.
$182 nightly
The price is $182
Nov 7 - Nov 8
Total with taxes and fees
A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye
A wooden deck with two wooden chairs and a table, a hot tub, and a building with a door open to a kitchen area.

8. Challenger - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom

Challenger - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
Tenterden
9.2 out of 10, Wonderful, (11 reviews)
"What a beautiful stay , peaceful , everything you could need for a well needed escape . Staff excellent , surroundings wonderful , bar / restaurant fantastic . Can’t wait to go back ."
United States
Anonymous traveler
$273 nightly
The price is $273
Nov 23 - Nov 24
Total with taxes and fees
Challenger - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
A small wooden cabin with a porch, a bench, and string lights, surrounded by trees under a starry sky.

9. The Field View 2 by Tiny Away

The Field View 2 by Tiny Away
Egerton
$139 nightly
The price is $139
Nov 8 - Nov 9
Total with taxes and fees
The Field View 2 by Tiny Away
A modern bedroom with a large bed, a bedside table, a desk, and a window.

10. The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom

The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
Rye
9.8 out of 10, Exceptional, (8 reviews)
"Had a great time, thank you very much ! Would definitely stay again! Good location, easy to get into Rye and surounds."
United States
Anonymous traveler
$273 nightly
The price is $273
Nov 8 - Nov 9
Total with taxes and fees
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
A cozy interior with a wood-burning stove, a kitchen area, a sofa, and a view of the outdoors.

11. Extraordinary Huts

Extraordinary Huts
3.0 star property
Rye
9.6 out of 10, Exceptional, (45 reviews)
"A stunningly beautiful setting. Clean, tidy and, elegantly decorated and set out. Secure, peaceful and comfortable. We shall most definitely stay there again. Cannot recommend highly enough! ✨💫✨💫✨💫💚🌲💚💫✨💫✨"
United Kingdom
Diana
$196 nightly
The price is $196
Nov 17 - Nov 18
Total with taxes and fees
Extraordinary Huts
A brick house with a large open doorway leading to a dining area.

12. Vine Cottage

Vine Cottage
3.5 star property
Tenterden
$624 nightly
The price is $749
Nov 13 - Nov 14
Total with taxes and fees
Vine Cottage
A cozy bedroom with a wooden headboard, a bed with patterned pillows, bedside lamps, and a decorative sign on the wall.

13. Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
East Sussex
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful property and absolutely lovely host."
United States
Alyson B.
$183 nightly
The price is $183
Nov 18 - Nov 19
Total with taxes and fees
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
A wooden deck with a hot tub, a wooden fence, and a gazebo.

14. The Yurt Den @ The Outside Inn

The Yurt Den @ The Outside Inn
Mountfield
$189 nightly
The price is $189
Nov 10 - Nov 11
Total with taxes and fees
The Yurt Den @ The Outside Inn
A rustic wooden cabin with a covered outdoor seating area, surrounded by lush greenery and a gravel path.

15. Birch Cottage: Starlit Soaks and Wood-Fired Warmth hot tub

Birch Cottage: Starlit Soaks and Wood-Fired Warmth hot tub
maidstone
9.8 out of 10, Exceptional, (10 reviews)
"Lovely property with a great location, a 5 minute drive from Leeds Castle! Very friendly host and accompanying doggie! Both properties also had great wood burner hot tubs which were fantastic."
United Kingdom
Samuel
$263 nightly
The price is $263
Nov 23 - Nov 24
Total with taxes and fees
Birch Cottage: Starlit Soaks and Wood-Fired Warmth hot tub
A cozy interior with a sofa, a lamp, and a window with curtains.

16. Meadow Sweet - a holiday let that sleeps 2 guests in 1 bedroom

Meadow Sweet - a holiday let that sleeps 2 guests in 1 bedroom
Burwash
10.0 out of 10, Exceptional, (1 review)
"Perfect place for the perfect getaway! We absolutely loved the cabin and enjoyed every minute of our stay. It was equipped with absolutely everything we needed, and the owner was the sweetest. We can’t wait to be back!"
United States
Anonymous traveler
$262 nightly
The price is $262
Nov 9 - Nov 10
Total with taxes and fees
Meadow Sweet - a holiday let that sleeps 2 guests in 1 bedroom
A covered outdoor patio with a seating area, a hot tub, and a small table.

17. The Lodge @The Outside Inn

The Lodge @The Outside Inn
Mountfield
$193 nightly
The price is $193
Nov 23 - Nov 24
Total with taxes and fees
The Lodge @The Outside Inn
A hot tub, seating area, and pergola with string lights in a backyard setting.

18. The Retreat @The Outside Inn

The Retreat @The Outside Inn
Mountfield
$178 nightly
The price is $178
Nov 16 - Nov 17
Total with taxes and fees
The Retreat @The Outside Inn
A bedroom with a large wardrobe, a desk with a chair, a bed, a window, and a radiator.

19. The Lower Bell

The Lower Bell
3.0 star property
Aylesford
7.8 out of 10, Good, (157 reviews)
"Small clean well appointed room in outbuilding. Large free car park. Good WiFi. Friendly helpful staff. No food available on sight."
United Kingdom
John
$78 nightly
The price is $94
Nov 6 - Nov 7
Total with taxes and fees
The Lower Bell
A traditional building with a black and white facade, multiple windows, and a sign for 'Swan Cottage Tea Rooms'.

20. An unusual two-storey apartment with beams and an open fire.

An unusual two-storey apartment with beams and an open fire.
Rye
10.0 out of 10, Exceptional, (11 reviews)
"Lovely little flat enjoyed the central location of the flat would definitely recommend "
United States
Robert E.
$266 nightly
The price is $266
Nov 12 - Nov 13
Total with taxes and fees
An unusual two-storey apartment with beams and an open fire.
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.
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Top Benenden Hotel Reviews

A large brick building with a garden patio featuring outdoor furniture and umbrellas.
Sissinghurst Castle Farmhouse

Sissinghurst Castle Farmhouse

Sissinghurst Castle Farmhouse
Cranbrook

10/10 Excellent

Fantastic place to stay next door to the Sissinghurst Castle Gardens. Friendly and beautiful. We will definitely return
United States
Katherina
Reviewed September 26, 2026
Sissinghurst Castle Farmhouse

Find out more about Benenden

Everything you need to know about Benenden vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Benenden vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Benenden vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Benenden vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Benenden. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Benenden in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $94 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Benenden rentals

At Expedia, we put the best Benenden vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Benenden rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Benenden vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Benenden. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Benenden?

Yes, we have vacation rentals near the most popular local attractions in Benenden, or you can select a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Benenden has to offer?

Fabulous 5 bed house with indoor swimming pool and hot tub in 1066 Country: Visitors like this Benenden vacation home rental. It offers an indoor pool, a patio, and laundry facilities to help you feel perfectly comfortable in your new surroundings. You can relax into your vacation with a garden and a hot tub.

How many vacation rentals will I find in Benenden?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Benenden stay.

What can I see and do in Benenden?

High Weald and Hole Park Gardens are a couple of lovely local spots to get outside and enjoy nature. Sissinghurst Castle and Garden and Great Dixter House and Gardens are a couple of places you'll find in the larger area.

What’s a vacation rental in Benenden like?

Vacation rentals are private properties you can book for a long or short time in Benenden. Vacation rentals feature amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family getaway.

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