Family-friendly vacation rentals in Benenden

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Top-rated family-friendly rentals in Benenden

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favourite
The cabin showcases a wooden exterior with a welcoming deck, furnished with outdoor chairs. Surrounding greenery adds to the serene setting, while a gently sloped area leads up to the entrance, framed by a rustic fence.
Cottage in Sandhurst
4.97 out of 5 average rating, 374 reviews

The Cabin - a little ranch house. A peaceful haven

Located in the High Weald area of Kent which is an AONB, The Cabin at Valley View Farm is set in its own space amongst 16 acres of wood and grazing. It used to be an old hop pickers mobile home but has been lovingly restored to a modern, well presented “mini” haven. A fully self-contained cabin with open plan lounge/dining/kitchen area, UK king size bed in bedroom and a shower room and toilet. Ideal for a couple or two singles as a Z-bed can be provided. Private outside veranda with a fire pit

Top guest favourite
A play area featuring a wooden climbing frame with a slide, swings, and a large sunken trampoline. Surrounding the equipment is a soft mulch surface, complemented by a grassy landscape and mature trees in the background under a partly cloudy sky.
Barn in Cranbrook
4.94 out of 5 average rating, 172 reviews

Cosy & Modern Converted Stable In Rural Kent

‘Little Hartleys’ is a detached, converted stable with cosy wood burning stove. Perfect for families where children can use our play park complete with sunken trampoline and zip wire and visit our chickens. From time to time, other animals will be housed on the property. Country walks start opposite the main entrance & within 1.5 miles you can find yourselves in our charming local pubs. Stable with private parking & outdoor area set behind a fence within the main residence on 2 acres of land

Guest favourite
A charming hut is set in a lush garden, featuring a wood-burning stove chimney. The exterior showcases large windows framed in green, allowing natural light. An outdoor seating area and fire pit are positioned on gravel, surrounded by well-maintained grass and greenery.
Shepherd’s hut in Cranbrook
4.96 out of 5 average rating, 120 reviews

The Foxy Shepherd - an idyllic country retreat

The hut is in a secluded fenced off part of our garden in a designated area of outstanding natural beauty with uninterrupted views over paddocks towards Benenden and provides the perfect retreat for couples looking for a place for complete relaxation and escape from daily life. It is completely self contained with an ensuite shower room, kitchen area, wood burning stove and cosy double bed. Outside is a fire pit with BBQ where you can enjoy the long summer evenings with a glass of wine and BBQ

Guest favourite
A restful bedroom features a super kingsize bed with white linens and textured pillows. Complementing nightstands with lamps are positioned on either side. A round mirror and artwork enhance the tranquil atmosphere, while soft light illuminates the soothing green walls.
Cottage in Benenden
4.97 out of 5 average rating, 152 reviews

Old Fire Station in central Benenden village, Kent

Nestling in the idyllic Weald of Kent countryside, the Old Fire Station is the perfect place for a relaxing stay in the centre of historic Benenden village. The spacious, self-contained accommodation sleeps four, with a separate bedroom with super kingsize bed and sitting room with two single sofa beds. The listed former village fire station is within walking distance of The Oak Barn wedding venue and Benenden School, or a short drive to Benenden Hospital and the gardens of Sissinghurst Castle.

Top guest favourite
A small wooden cabin is set against a backdrop of lush greenery and a clear blue sky. Several sheep graze peacefully in the vibrant green grass surrounding the cabin, with a wooden fence delineating the area.
Farm stay in Biddenden
4.97 out of 5 average rating, 287 reviews

Ayleswade shepherd hut in Kent countyside

set in the small village of biddenden in the heart of the kent countryside belonging to a local farming family of many generations .You can expect beautiful country walks with many footpaths and local villages nearby for cream teas and lovely lunches , the nearby village of Headcorn with its straight connections to London or the coast is good for sightseeing, you wake up to views of our sheep and free range chicken and enjoy a relaxing cup of tea.Theres milk ,tea and coffee and our eggs for you

Top guest favourite
The Garden Studio is presented with large floor-to-ceiling windows featuring soft curtains. A wooden deck is adorned with a seating area, surrounded by manicured grass and flowering plants, offering a serene outdoor space for relaxation.
Guesthouse in Sissinghurst
4.93 out of 5 average rating, 181 reviews

Self Contained Garden Studio with stunning views

The Garden Studio has spectacular views over the Kent countryside from the property's floor to ceiling windows. The self contained compact studio has private access and includes lounge chairs, coffee table and a double bed. We have a dining table/ two stools overlooking the terrace. There is a fridge, a microwave, a two ring electric hob together with a kettle, Nespresso Coffee Machine and a toaster in the kitchen area. Iron/Board/Desk/Chair are on request prior to stay. Compact shower/wc.

Top guest favourite
A decked terrace extends from large sliding glass doors, offering access to the outdoor space. Two minimalist white chairs are positioned on the terrace, facing a serene view of the landscape beyond. Soft outdoor lighting enhances the wooden exterior of the building.
Guesthouse in Iden Green
4.95 out of 5 average rating, 104 reviews

Contemporary rural retreat with breathtaking views

The Rookery is a newly built space with stunning South-facing views across an Area of Outstanding Natural Beauty. The ideal base to explore the Kent & Sussex countryside & coast: Ancient forests & villages, historic castles, famous beaches and cosy local pubs. Just 15 min to Sissinghurst Castle & garden, Bodiam & Scotney Castle, 20 min to Rye & 30 min to the dunes & beaches at Camber. Explore local walks, Go Ape at Bedgebury Forest, paddleboarding & watersports or tour our local wineries.

Top guest favourite
A rustic home is surrounded by lush greenery, with a spacious garden inviting relaxation. The exterior features a warm color palette, complemented by large windows and a welcoming terrace that provides access to the garden.
Barn in Kent
4.95 out of 5 average rating, 139 reviews

Sissinghurst Stables in the Garden of England.

Sit and enjoy the large private garden from the sunny south -facing terrace. This rustic home has an authentic feel, with a quirky calming country design, interspersed with antique furniture and botanical artwork throughout. There is a separate TV room and magical mezzanine play area with baskets of toys for children. There is a private, sunny, nature filled garden. Only one hour from London by train which makes it a perfect location for a city trip too. Insta: Sissinghurst_stables_airbnb

Guest favourite
Cottage in Benenden
4.9 out of 5 average rating, 260 reviews

The Paper Mill Stables

Set in the beautiful grounds of a fifteenth century Wealden hall house, The Stables is a delightful oak framed cottage - a hidden-away and peaceful haven for two. There is a sitting room with woodburner for super cosy nights in, and the pretty bedroom has a luxurious 4000 pocket sprung king size bed, and quality Egyptian cotton linen. Outside is a secluded garden with a terrace, and seventy acres of woodland and pasture to wander through; our resident Labradors will be pleased to join you!

Top guest favourite
A charming black timber cottage is surrounded by lush greenery and neatly trimmed hedges. A well-maintained lawn extends in the foreground, leading to a wooden fence that provides a sense of privacy while natural light enhances the serene landscape.
Guesthouse in Biddenden
4.96 out of 5 average rating, 130 reviews

Little Batchelors - Idyllic escape

Set in the grounds of a stunning 400 year old Tudor Hall and gardens, this beautiful new property is 1.5 miles away from the gorgeous Sissinghurst Castle Garden and within easy reach of Biddenden, with its renowned vineyard and Michelin starred restaurant. A perfect setting for couples, small families or friends. It has a very large open plan living/dining/kitchen area with doors onto a decked terrace and two en-suite double bedrooms, with ample room for parking.

Top guest favourite
The historic windmill features a distinctive white weatherboard structure, surrounded by lush greenery. Two teak steamer chairs are positioned in the foreground, inviting relaxation in the garden. A clear blue sky with soft clouds enhances the serene rural setting.
Windmill in Benenden
4.99 out of 5 average rating, 817 reviews

Old Smock Windmill in rural Kent

Old Smock Mill is a romantic place for couples. The atmosphere inside is peaceful and relaxing. Everything is designed to unwind you from the moment you walk in. It is surrounded by the lovely Kent countryside where you can ramble and refresh yourselves by perhaps ending the day in one of the great pubs cosy by a log fire in Winter or in Summer in an English garden. Guests have said how hard it is to tear themselves away, it truly is a treasure to find.

Guest favourite
A gravel pathway winds beside a dark gray building adorned with climbing roses and brightly colored flower pots. A window provides a glimpse of the exterior, while lush greenery and trees frame the scene under a partly cloudy blue sky.
Farm stay in Bodiam
4.78 out of 5 average rating, 226 reviews

Adorable Hideaway: log stove, campfire, organic fm

The Adorable Hideaway is situated in the generally quiet farmyard of a thirty acre organic smallholding, a mile from Bodiam Castle. People said I would never find a place like this in South East England and I’d have to go at least to Devon, but here we are, at the farm that forgot the time. To come and go, you don’t have to go past my home or into my garden, I think people find the hideaway quite adequately private. It's a bit busier these days..

Popular amenities for Benenden family-friendly rentals

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Avg. price$259 CAD$262 CAD$270 CAD$322 CAD$304 CAD$322 CAD$270 CAD$270 CAD$269 CAD$301 CAD$278 CAD$291 CAD
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Quick stats about vacation rentals that are family-friendly in Benenden

  • Total vacation rentals

    Explore 30 vacation rentals in Benenden

  • Nightly prices starting at

    Benenden vacation rentals start at $182 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,110 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Benenden vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Benenden rentals

  • 4.9 Average rating

    Benenden stays are highly rated by guests—averaging 4.9 out of 5!

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