Vacation rentals in Cranbrook & Sissinghurst

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Top-rated vacation rentals in Cranbrook & Sissinghurst

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Shepherd’s hut in Cranbrook
4.96 out of 5 average rating, 118 reviews

Spacious luxury shepherds hut with woodburner

The Sheepcote, our brand new spacious shepherds hut, is based in the Kent High Weald Area of Outstanding Natural Beauty. It sits in its own south facing half acre garden with fruit trees, silver birch and a young oak tree. Outside there’s plenty of parking and an area with a bench, table and chairs where you can relax and enjoy the countryside, watch the buzzards fly overhead and in the evenings listen out for the soft hooting of our resident owls! Its the perfect place for a romantic break.

Top guest favorite
Cottage in Benenden
4.98 out of 5 average rating, 151 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 favorite
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.

Guest favorite
Apartment in Hartley
4.92 out of 5 average rating, 103 reviews

Spacious self contained flat and private garden.

Welcome to Courtney Lodge – a spacious one bedroom flat with private entrance, garden/patio. Off street parking. Walking distance from Cranbrook the 'Wealden Capital' in an Area of Outstanding Natural Beauty. This fully furnished ground floor flat is completely self contained with open living room/ kitchen leading to a separate bedroom and ensuite bath/ shower room. Big enough for short or long term stay. Free Wifi. Sorry, no pets/ parties/events. No smoking. Not suitable for young children.

Guest favorite
Barn in Staplehurst
4.96 out of 5 average rating, 313 reviews

Hoppers' Hideaways -The Hop Barn - Kent

Situated in the heart of the Kent countryside, this historic barn has been modernised but yet still retains it's unique character and charm. The Hop Barn is the perfect getaway from the hustle and bustle of everyday life where you can enjoy walks through the nearby orchards or simply sit on the patio and listen to the sound of nature. For those wanting to explore, the barn is conveniently located nearby to renowned gardens, castles, stately homes, forests, quaint villages and historic towns.

Top guest favorite
Cottage in Sandhurst
5 out of 5 average rating, 273 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.

Top guest favorite
Barn in Kent
4.95 out of 5 average rating, 135 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 favorite
Cottage in Benenden
4.9 out of 5 average rating, 259 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!

Guest favorite
Loft in Cranbrook
4.87 out of 5 average rating, 166 reviews

Letterbox Retreat (EV Friendly)

A delightful retreat set in a private garden of 4 acres. Guests have use of the Astro Tennis Court, a must for Tennis fans!. Plenty of public footpaths to explore which can take you through bluebell woods and along the way to some lovely local Gastropubs. The property is 5 miles from Benenden School, (ideal for parents for Saturday Sports). It is also great as a stop off for larger families for Le Eurotunnel (45mins away). 75Mb Unlimited Wifi. Sky TV, Trampoline & BBQ

Top guest favorite
Windmill in Benenden
4.99 out of 5 average rating, 814 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 favorite
Condo in Kent
4.91 out of 5 average rating, 149 reviews

St. David's House in the heart of Cranbrook

St. David's House was a coffee tavern in the 1880s. It's in the heart of beautiful Cranbrook, close to Union Mill, a working windmill which you can see from the bedroom. A minute's walk takes you to local pubs, restaurants, cafes, and independent shops. The Apartment is spacious, with an open plan kitchen/diner/lounge, bathroom with bath & shower, one double bedroom & a comfortable double sofa bed. Private secure parking. Well behaved pets welcome.

Guest favorite
Guesthouse in Cranbrook
4.92 out of 5 average rating, 180 reviews

Cosy, well-equipped Studio in Oak-Beamed Stable

Take it easy at this unique and tranquil getaway. This historic oak-beamed stable set within the grounds of a former Kent farm, is the perfect base for those wishing for a weekend away or longer to explore the Kent and Sussex countryside. With access to a large garden at the rear with amenities including a firepit, outside dining and seating area, BBQ, Hammock and pond jetty. Use of a large bell tent can also be included for an additional fee.

Popular amenities for Cranbrook & Sissinghurst vacation rentals

Quick stats about vacation rentals in Cranbrook & Sissinghurst

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Frequently Asked Questions

  • Do house rentals in Cranbrook have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Cranbrook. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Cranbrook?

    Make yourself at home in Cranbrook by choosing from our most frequently booked neighborhoods. We have over 130 vacation rentals in Cranbrook, and over 70 vacation rentals in Hartley.

  • What are the most popular amenities for House Rentals in Cranbrook?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Cranbrook have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Cranbrook. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Cranbrook?

    Cranbrook has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Cranbrook?

    Experience the best of Cranbrook with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.