Cottage vacation rentals in Cranbrook & Sissinghurst

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Top-rated cottage rentals in Cranbrook & Sissinghurst

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Top guest favorite
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

Guest favorite
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.

Guest favorite
An inviting outdoor patio features a rustic wood-fired oven, surrounded by greenery. Comfortable lounge furniture and a wooden table are present, with potted plants adding a touch of nature. A patterned area rug enhances the space, creating an ideal spot for relaxation.
Cottage in Kent
4.9 out of 5 average rating, 146 reviews

Idyllic 2- Bedroom barn with amazing views

Spacious barn conversion with views of the countryside. The Barn is an ideal location to use as a base for visiting the many places of interest or for a relaxing holiday. There are many National Trust properties within a small radius together with historic gardens and local vineyards. Tenterden and Rye are a short drive and Camber Sands, with its sandy beach, is a must. There are a number of local pubs which serve food, The White Hart within a few minutes walk, and many others not far away.

Top guest favorite
A vaulted studio features exposed oak beams and large glass doors that open to scenic views. A spacious sofa is arranged around a circular coffee table, while a comfortable bed is positioned in the background. Decorative plants and artwork enhance the warm atmosphere.
Cottage in Sandhurst
5 out of 5 average rating, 275 reviews

Stylish, Oak Vaulted Studio with Countryside Views

The Grade II listed Bakehouse, like its beautiful neighbouring holiday accommodation Cowbeach Cottage, has a wealth of character and has been lovingly restored to a high standard. The Bakehouse can be booked alone or with the Cottage for two couples who wish to holiday together, whilst enjoying their own space. The charming, bright and tastefully decorated vaulted studio features a wealth of oak beams and benefits from its own south facing garden, patio and verandah with far reaching views.

Guest favorite
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 favorite
A wooden sign displaying 'The Cottage' is positioned in the foreground, crafted with a detailed design. In the background, the cottage structure with a dark exterior is partially visible, surrounded by lush greenery and a gravel path leading to a fenced area.
Cottage in Saint Michaels
4.99 out of 5 average rating, 128 reviews

The Cottage at high chimney farm

High Chimney Farm Cottage Nr Tenterden offers the warmest welcome in Kent, modern and comfortable bedrooms, offering the perfect base to explore the best of the Kentish Weald and beyond. The Cottage is a former Granary beautifully converted into self contained luxury accommodation ideal for overnight, short stays or a full holiday let if required. You are more than welcome to enjoy our large garden and pond! It’s a short walk or you could drive up if you wish, so peaceful!

Top guest favorite
The exterior of the eco-friendly cottage is framed by an array of flowering plants and gravel pathways. Natural wood cladding complements the blue sky. Outdoor seating includes a dining table and chairs, inviting relaxation in the spacious garden area.
Cottage in Brightling
5 out of 5 average rating, 159 reviews

The Long Stable: Rural haven, spacious, fast Wifi

Stylishly fitted and eco-friendly, our detached, self-contained cottage is in a very rural location. There are no other holiday cottages on the farm. Situated in the High Weald Area of Outstanding Natural Beauty, on a sheep farm of 23 acres (which you are free to roam), this is a real get-away-from-it-all location. One of the most peaceful and relaxing places you will ever stay. With underfloor heating and a wood-burning stove you will be cosy whatever the weather.

Guest favorite
The exterior of the annex is presented, featuring a white picket fence and a gravel area. A vintage lamppost stands near the entrance, complemented by two outdoor chairs positioned on the patio. The structure showcases a pitched roof, rustic siding, and several windows, providing ample natural light.
Cottage in Boughton Monchelsea
4.9 out of 5 average rating, 794 reviews

The Oast Cottage: Private Annex with own entrance.

We are pleased to offer our refurbished annex with double bedroom, private bathroom, own front door and a private field for dogs. Oast Cottage is a converted stables attached to the main Oast House. The Oast is set in a conservation area of Boughton Monchelsea which consists of converted farm buildings, listed houses and a 16th Century pub (directly opposite). The area boasts many places to visit (including Leeds Castle), countryside walks, as well as numerous pubs.

Guest favorite
A covered outdoor area is illuminated by string lights, showcasing a large table and various seating options. Two comfortable lounge chairs are accentuated by a patterned rug. Lush greenery surrounds the space, creating an inviting atmosphere for gatherings or relaxation.
Cottage in Sissinghurst
4.92 out of 5 average rating, 200 reviews

Heated covered garden. Wlk to Sissinghurst Castle

The Outside Inn is a newly renovated 19th Century weatherboard barn. It has an open plan kitchen/dining/living area. There is 1 large bedroom with a Super King bed There is 1 bathroom with a large walk in powerful shower. The kitchen is fully equipped with oven, dishwasher, coffee machine etc. The sitting area has a very comfortable sofa. There’s a 9m x 4m covered outside area - bbq, dining, sofa, and heaters to make it useable all year round

Top guest favorite
A spacious living area showcases wooden beams and an open layout. A comfortable sofa faces a wood-burning stove, with a flat-screen TV nearby. The dining table is surrounded by woven chairs, and large windows provide natural light while offering views of the entrance and surrounding nature.
Cottage in Marden
4.99 out of 5 average rating, 573 reviews

The Lodge

**Opted in to Airbnb's enhanced cleaning protocol** Cosy barn-style accommodation nestled in the heart of the Kent countryside. Located close to National Trust sites and country walks. The Lodge is the perfect country getaway and romantic retreat. Please note this is strictly a NO SMOKING property inside the Lodge, the garden and surrounding field. The property is also NOT SUITABLE for infants, children or pets. Two adults only.

Top guest favorite
A thatched cottage is seen set against a backdrop of vibrant greenery, beside a tranquil pond adorned with water lilies. The well-manicured lawn features neatly striped grass, enhancing the serene outdoor setting. Sunlight illuminates the scene under a clear blue sky.
Cottage in Rotherfield
4.98 out of 5 average rating, 325 reviews

The Granary at Coes Vineyard, East Sussex

Coes Farm offers 50 acres of absolute tranquillity in amongst nature, with a bit of luxury thrown in too! We have formal gardens and ornamental ponds, a large lake, plenty of woodland, open fields, an indoor saltwater swimming pool with hot tub, a tennis court and a games room which is resident in our Micro-Winery! We planted our 5 acre vineyard in Spring 2021 and extended the existing Orchard with cider varieties in 2023.

Top guest favorite
The open-plan living area features exposed wooden beams, enhancing the spacious feel. Comfortable sofas are arranged around a wooden coffee table, with a TV visible in the corner. A fully equipped kitchen is positioned in the background, integrating modern functionality with rustic charm.
Cottage in Tenterden
4.96 out of 5 average rating, 527 reviews

Pickle Cottage Tenterden

We would love to welcome you to our converted timber framed building (once a pig shed!) with modern furnishing, wooden floors and high ceilings. 1 double and 1 twin bedroom. Fully equipped kitchen, WiFi, Freeview TV, walk-in shower. Peaceful Kent countryside location, set in half an acre of garden, 1 mile from Tenterden. Great for weekend getaways, family holidays and an ideal venue for small business meetings.

Popular amenities for Cranbrook & Sissinghurst cottage rentals

Quick stats about cottage rentals in Cranbrook & Sissinghurst

  • Nightly prices starting at

    Cranbrook & Sissinghurst vacation rentals start at G$29,318 GYD per night before taxes and fees

  • Verified guest reviews

    Over 170 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Cranbrook & Sissinghurst rentals

  • 4.8 Average rating

    Cranbrook & Sissinghurst stays are highly rated by guests—averaging 4.8 out of 5!