
Cottage holiday rentals in Cranbrook & Sissinghurst
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Top-rated cottage rentals in Cranbrook & Sissinghurst
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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

Cosy Cottage with Woodburner & Countryside Views.
Cowbeach Cottage is Grade II listed and has been lovingly restored to a high standard. It features a wealth of old oak beams and an inglenook fireplace with a cosy wood burning stove. It is tastefully decorated throughout to provide a relaxing space. The bespoke oak staircase leads to a beautiful vaulted bedroom with views across the Kent countryside. The cottage benefits from a private south facing garden and patio. It is ideally situated to explore the many National Trust properties close by.

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.

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!

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!

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.

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

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.

The Granary, Organic Vineyard stay with Pool.
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.

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.

Peaceful Cottage with Views nr Sissinghurst Castle
Weaver's Rest offers peace and tranquility in the garden of England within easy reach of beautiful walks, English Heritage sites, and medieval villages. This well-equipped cottage is situated in the stunning High Weald Area of Outstanding Natural Beauty. Local pubs, shops & restaurants are within walking distance or enjoy your own meals gazing over surrounding countryside at home. The hosts live next-door.

Perfect Isolation. Quaint Sussex Farm Cottage
Refurbished Spring ‘22 The perfect rural bolthole. Think The Holiday but you will need to supply Jude Law & Cameron Diaz. Waggoners is a private & quaint, cottage set in idyllic isolation, on a working farm, with luxurious handpicked furnishings. Outside- you are spoilt with a patio that bathes in sunshine all day. Please also see my other listings for further availability
Popular amenities for Cranbrook & Sissinghurst cottage rentals
Cottage rentals with a hot tub

Oak Cottage: Hot Tub, Large Patio & Alpaca Views

Evegate Manor Barn

Plantagenet: A Historic Country Cottage with Pool

Thatched Cottage Kent hideaway 3 Bed HotTub Haven!

Blackthorn is a luxurious, rural retreat for two.

Badgers Den - Covehurst Bay Holiday Cottage

Beautiful, Winter Retreat + Hot Tub

Romantic retreat for 2 with hot tub & woodburner
Pet-friendly cottage rentals

Peace, Quiet, Cosy house with garden & log burner

Peaceful Idyllic Stable on Romney Marsh near Rye

Setts Wood Cottage, Tenterden

Pretty Converted Barn with Private Sun Terrace and Garden

The Stable Cottage on beautiful farm

The Workshop near Rye

The Hay Loft, Idyllic Rural Sussex Retreat

Tenterden High Street Cottage for 4 ( 2 bedrooms)
Private cottage rentals

Dungeness fisherman’s cottage full of character.

Hazel Tree Cottage. A secluded country retreat.

Castle Cottage, Wadhurst

Wild hideaway near Lewes

The Cow Shed - Rolvenden

Mafeking - 3 bedroom cottage with games room

Twitchers Cottage Oare - Nature on your doorstep

Cosy Private Cottage in Wrotham, Kent Downs AONB
Quick stats about cottage rentals in Cranbrook & Sissinghurst

Nightly prices starting at
Cranbrook & Sissinghurst holiday rentals start at $243 NZD per night before taxes and fees

Verified guest reviews
Over 170 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Cranbrook & Sissinghurst rentals

4.8 Average rating
Cranbrook & Sissinghurst stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Tower Bridge
- Big Ben
- London Bridge
- Westminster Abbey
- British Museum
- Covent Garden
- Buckingham Palace
- Hampstead Heath
- The O2
- Trafalgar Square
- St Pancras International
- Emirates Stadium
- Wembley Stadium
- St. Paul's Cathedral
- ExCeL London
- Camden Market
- London Stadium
- Clapham Common
- Alexandra Palace
- Primrose Hill
- Queen Elizabeth Olympic Park, London
- Hampton Court Palace
- Folkestone Beach
- Twickenham Stadium




