Benenden Vacation Rentals from CA $131: Short-Term Rentals for 2026

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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

Benenden

Hartmut K.

CA $1,380 total

includes taxes & fees

Nov 2 - Nov 3

A modern kitchen with a central island, pendant lights, and a view of the outdoors.

2. The Pigsty at the Secret Garden

Ashford

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

Tenterden

Rebecca J.

CA $417 total

includes taxes & fees

Oct 27 - Oct 28

A brick house with a large open doorway leading to a dining area.

4. Vine Cottage

Tenterden

CA $951 total

includes taxes & fees

Nov 13 - Nov 14

An open door leading to a wooden deck with a view of a green landscape and trees.

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

Tenterden

Dean

CA $381 total

includes taxes & fees

Oct 27 - Oct 28

A wooden deck with a wooden chair and table, a blanket, and breakfast items.

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

Tenterden

Harry I.

CA $346 total

includes taxes & fees

Oct 26 - Oct 27

A wooden cabin with a hot tub, a covered deck, and a sign reading "Cascade."

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

Tenterden

Anonymous traveller

CA $381 total

includes taxes & fees

Oct 27 - Oct 28

A modern bedroom with a large bed, a bedside table, a desk, and a window.

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

Rye

Anonymous traveller

CA $381 total

includes taxes & fees

Oct 26 - Oct 27

A greenhouse structure surrounded by yellow flowering plants.

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

Rye

"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."

Kerry H.

CA $265 total

includes taxes & fees

Oct 26 - Oct 27

A cozy interior with a wood-burning stove, a kitchen area, a sofa, and a view of the outdoors.

10. Extraordinary Huts

Rye

Diana

CA $277 total

includes taxes & fees

Oct 27 - Oct 28

A wooden deck with two wooden chairs and a table, a hot tub, and a building with a door open to a kitchen area.

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

Tenterden

Anonymous traveller

CA $381 total

includes taxes & fees

Oct 26 - Oct 27

A modern bedroom with a large bed, a sitting area with a chair, and a view of the garden through a glass door.

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

Rye

"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"

Lynn B.

CA $360 total

includes taxes & fees

Oct 26 - Oct 27

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

East Sussex

Alyson B.

CA $266 total

includes taxes & fees

Oct 26 - Oct 27

A brick wall with a stone base, a wooden gate, and two planters with soil.

14. 3 Cinque Ports Street

Rye

CA $800 total

includes taxes & fees

Oct 29 - Oct 30

A traditional building with a black and white facade, multiple windows, and a sign for 'Swan Cottage Tea Rooms'.

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

Rye

Robert E.

CA $369 total

includes taxes & fees

Nov 12 - Nov 13

A small wooden cabin with a porch, a bench, and string lights, surrounded by trees under a starry sky.

16. The Field View 2 by Tiny Away

Egerton

CA $193 total

includes taxes & fees

Oct 26 - Oct 27

A balcony with a wooden fence, potted plants, and a view of a green landscape.

17. 1 bedroom accommodation in Battle

Battle

John

A secluded outdoor area with two small, semi-circular wooden structures, surrounded by lush greenery and trees.

18. Chestnut Meadow Camping

Bexhill-on-Sea

Mary

CA $141 total

includes taxes & fees

Oct 26 - Oct 27

A bedroom with a bed, a desk, and a chair.

19. The Lower Bell

Aylesford

John

CA $131 total

includes taxes & fees

Oct 27 - Oct 28

A two-story brick house with a visible front door, a small porch, and a fenced yard.

20. Charming 3-bedroom house in soothing Playden Rye neighborhood

Playden, Rye

Edward W.

CA $620 total

includes taxes & fees

Oct 27 - Oct 28

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Top Benenden Hotel Reviews

Royal Wells Hotel

10/10 Excellent

"Firstly the staff were very attentive. At the start when checking in the guy behind the desk asked what we were up to for the day so he could further assist. Really friendly service that a lot of places don't consider these days. The room was clean with a lovely note from the service staff. The room was also a lot bigger than expected and nicely decorated. After going out for some dinner, my wife and I came back for a drink in the bar and they had Damm Lemon!! DAMM LEMON!!! Unreal to have such a rare beer in a hotel bar. The next day we came down for breakfast and were served quickly and thoroughly with a really tasty and well cooked breakfast. All in all it was a fantastic stay with really friendly staff, good food and great drinks!!!!!"

Hempstead House Hotel

10/10 Excellent

"We had a great stay. We were only there one night but the room was lovely, bed comfortable and Spa very clean and welcoming. We had an evening meal and some drinks. The service was great and food delicious. All drinks and food were excellent value. Breakfast was plentiful and very good. The hotel is comfortable with plenty of areas to sit and relax. My only quibble was the room was cold when we arrived but soon warmed up when we turned the radiator on. I would highly recommend."

ORIDA Maidstone Hotel

10/10 Excellent

"We had a lovely stay at the Orida Hotel in Maidstone! The hotel was clean, comfortable, and welcoming, with friendly staff who made the experience even better. The swimming pool was a real highlight and a great way to relax and unwind during our stay. The facilities were excellent, and the overall atmosphere was pleasant and relaxing. We really enjoyed our time here and would definitely recommend the hotel to anyone looking for a comfortable and enjoyable stay. We would happily return!"

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Benenden vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Benenden vacation rentals we have selected for you start as low as CA $131 per night. Entering your travel dates in the search wizard 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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Check prices for these dates

Our top choices for Benenden vacation rentals

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

2. The Pigsty at the Secret Garden

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

4. Vine Cottage

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

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

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

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

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

10. Extraordinary Huts

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

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

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

14. 3 Cinque Ports Street

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

16. The Field View 2 by Tiny Away

17. 1 bedroom accommodation in Battle

18. Chestnut Meadow Camping

19. The Lower Bell

20. Charming 3-bedroom house in soothing Playden Rye neighborhood

Find vacation rentals that suit your style

Top Benenden Hotel Reviews

Royal Wells Hotel

The Spa Hotel

Hempstead House Hotel

Village Hotel Maidstone

ORIDA Maidstone Hotel

The Lookout Rye

Holiday Inn Ashford Central by IHG

Find out more about Benenden

Frequently asked questions

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