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Holiday Rentals in Sissinghurst

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Sissinghurst holiday rentals

A restaurant interior with wooden tables and chairs, a bar area with a bartender, and a brick wall with framed pictures.

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

Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom
Tenterden
9.2 out of 10, Wonderful, (5 reviews)
"Has everything you need. Very clean and comfortable. Only problem was the light coming in early in the morning, may want to take a sleep mask with you if you’re a light sleeper. Other thank that could not fault it."
United States
Rebecca J.
The price is €264
includes taxes & fees
25 Oct - 26 Oct
Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom
An open door leading to a wooden deck with a view of a green landscape and trees.

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

Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
Tenterden
9.6 out of 10, Exceptional, (14 reviews)
"This was our first of hopefully many visits and we loved the whole vibe x The bed was so comfortable and we had a wonderful time x"
United States
Anonymous traveller
The price is €241
includes taxes & fees
22 Oct - 23 Oct
Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
A living room with a sectional sofa, a fireplace, and a TV mounted on the wall.

3. The Pigsty at the Secret Garden

The Pigsty at the Secret Garden
2.0 star property
Ashford
The price is €320
includes taxes & fees
22 Oct - 23 Oct
The Pigsty at the Secret Garden
A wooden deck with a wooden chair and table, a blanket, and breakfast items.

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

Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
Tenterden
9.0 out of 10, Wonderful, (6 reviews)
"Great little property, surprisingly comfortable for a small space, nice rural views from the lovely hot tub, and great beer from the onsite brewery!"
United States
Harry I.
The price is €219
includes taxes & fees
26 Oct - 27 Oct
Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
A wooden cabin with a hot tub, a covered deck, and a sign reading "Cascade."

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

Cascade - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
Tenterden
9.8 out of 10, Exceptional, (7 reviews)
"Found this place fairly last minute and couldn’t believe what a little gem it was. Gorgeous surroundings, an oasis of calm. We had a lovely stay."
United States
Anonymous traveller
The price is €241
includes taxes & fees
27 Oct - 28 Oct
Cascade - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
A wooden deck with two wooden chairs and a table, a hot tub, and a building with a door open to a kitchen area.

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

Challenger - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
Tenterden
9.2 out of 10, Wonderful, (11 reviews)
"What a beautiful stay , peaceful , everything you could need for a well needed escape . Staff excellent , surroundings wonderful , bar / restaurant fantastic . Can’t wait to go back ."
United States
Anonymous traveller
The price is €241
includes taxes & fees
22 Oct - 23 Oct
Challenger - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
A small wooden cabin with a porch, a bench, and a table.

7. The Field View 2 by Tiny Away

The Field View 2 by Tiny Away
Egerton
The price is €122
includes taxes & fees
25 Oct - 26 Oct
The Field View 2 by Tiny Away
A modern bedroom with a large bed, a sitting area with a chair, and a view of the garden through a glass door.

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

The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom
Rye
9.0 out of 10, Wonderful, (6 reviews)
"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"
United States
Lynn B.
The price is €228
includes taxes & fees
22 Oct - 23 Oct
The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom
A cozy interior with a wood-burning stove, a kitchen area, a sofa, and a view of the outdoors.

9. Extraordinary Huts

Extraordinary Huts
3.0 star property
Rye
9.6 out of 10, Exceptional, (45 reviews)
"A stunningly beautiful setting. Clean, tidy and, elegantly decorated and set out. Secure, peaceful and comfortable. We shall most definitely stay there again. Cannot recommend highly enough! ✨💫✨💫✨💫💚🌲💚💫✨💫✨"
United Kingdom
Diana
The price is €181
includes taxes & fees
22 Oct - 23 Oct
Extraordinary Huts
A cobblestone street lined with traditional buildings, some with ivy and flower boxes, and street lamps.

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

Mafeking by inspirestays-com - a cottage that sleeps 6 guests in 3 bedrooms
Benenden
9.8 out of 10, Exceptional, (21 reviews)
"A wonderful place for a holiday Nice location. Good opportunity for excursions to Hastings, Tenterden, Bodiam. Stop off at The Bull or the Milkhouse in Sissinghurst."
United States
Hartmut K.
The price is €874
includes taxes & fees
2 Nov - 3 Nov
Mafeking by inspirestays-com - a cottage that sleeps 6 guests in 3 bedrooms
A rustic wooden cabin with a covered outdoor seating area, surrounded by lush greenery and a gravel path.

11. Birch Cottage: Starlit Soaks and Wood-Fired Warmth hot tub

Birch Cottage: Starlit Soaks and Wood-Fired Warmth hot tub
maidstone
9.8 out of 10, Exceptional, (10 reviews)
"Lovely property with a great location, a 5 minute drive from Leeds Castle! Very friendly host and accompanying doggie! Both properties also had great wood burner hot tubs which were fantastic."
United Kingdom
Samuel
The price is €252
includes taxes & fees
22 Oct - 23 Oct
Birch Cottage: Starlit Soaks and Wood-Fired Warmth hot tub
A greenhouse structure surrounded by yellow flowering plants.

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

A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye
Rye
10.0 out of 10, Exceptional, (2 reviews)
"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."
United Kingdom
Kerry H.
The price is €174
includes taxes & fees
23 Oct - 24 Oct
A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye
A bedroom with a bed, a desk, and a chair.

13. The Lower Bell

The Lower Bell
3.0 star property
Aylesford
7.8 out of 10, Good, (155 reviews)
"Small clean well appointed room in outbuilding. Large free car park. Good WiFi. Friendly helpful staff. No food available on sight."
United Kingdom
John
The price is €83
includes taxes & fees
22 Oct - 23 Oct
The Lower Bell
A balcony with a view of a street, two potted plants, a bottle of wine, and a glass of wine on a small table.

14. St Andrews Apartments

St Andrews Apartments
4.0 star property
Maidstone
9.8 out of 10, Exceptional, (30 reviews)
"Very nice place to stay, clean, and lots of room. Our door areas are nice and great views from the balcony. "
United States
Stuart
The price is €247
includes taxes & fees
21 Nov - 22 Nov
St Andrews Apartments
A garden with a wooden house, a bench, and potted plants.

15. The Barn at Sandhole Cottage

The Barn at Sandhole Cottage
3.5 star property
Tonbridge
10.0 out of 10, Exceptional, (2 reviews)
"Lovely property in peaceful setting. Close to shops and amenities. Very useful location map showing local amenities and interesting places to visit. Welcoming hosts who were easy to get hold of. Pretty outdoor space to sit in. Everything in the property well thought out and organised."
United Kingdom
Karen
The price is €456
includes taxes & fees
31 Oct - 1 Nov
The Barn at Sandhole Cottage
A modern bedroom with a large bed, a bedside table, a desk, and a window.

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

The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
Rye
9.8 out of 10, Exceptional, (8 reviews)
"Stayed here for a night and wish it was longer. Beautiful clean place with an extremely comfortable bed. Will definitely be back. Thankyou to the hosts x"
United States
Anonymous traveller
The price is €241
includes taxes & fees
22 Oct - 23 Oct
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
A cozy bedroom with a wooden headboard, a bed with patterned pillows, bedside lamps, and a decorative sign on the wall.

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

Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
East Sussex
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful property and absolutely lovely host."
United States
Alyson B.
The price is €175
includes taxes & fees
22 Oct - 23 Oct
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
A traditional building with a black and white facade, multiple windows, and a sign for 'Swan Cottage Tea Rooms'.

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

An unusual two-storey apartment with beams and an open fire.
Rye
10.0 out of 10, Exceptional, (11 reviews)
"Lovely little flat enjoyed the central location of the flat would definitely recommend "
United States
Robert E.
The price is €234
includes taxes & fees
5 Nov - 6 Nov
An unusual two-storey apartment with beams and an open fire.
A building with a sloped roof, wooden entrance, and large windows.

19. 3 bedroom accommodation in Smarden, near Ashford

3 bedroom accommodation in Smarden, near Ashford
Smarden, near Ashford
10.0 out of 10, Exceptional, (1 review)
"A wonderful 4 nights spent at Romden farm, couldnt have been bette. It was great, just to open the back door and walk for miles with the dogs, come back chill out and relax in the hot tub in the evenings. At the big pond we enjoyed feeding the fish and watching the barn owl hunt at dusk. The barn was clean, comfortable and the perfect place to get away from everything. The owners made us feel so welcome we will definitley be back in the future."
United States
Louise
The price is €713
includes taxes & fees
30 Oct - 31 Oct
3 bedroom accommodation in Smarden, near Ashford
A large stone castle with multiple towers, a moat, and a grassy landscape.

20. Harvest View, Tilmangate Farm

Harvest View, Tilmangate Farm
Ulcombe
10.0 out of 10, Exceptional, (4 reviews)
"Lovely place to stay, very clean and modern with all the facilities you would want. Horses outside to entertain the kids and great location to explore. Would highly recommend! Review independently collected and verified by Reevoo"
United States
Laura
The price is €624
includes taxes & fees
7 Nov - 8 Nov
Harvest View, Tilmangate Farm
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sissinghurst Hotel Reviews

The Conningbrook Hotel

The Conningbrook Hotel

10/10 Excellent
"From the moment we entered till we left, we knew we had made the best choice by staying at The Conningbrook Hotel in Ashford. Tucked away of the main road only adds to the attraction of the experience. Staff were friendly and helpful upon arrival and the room was very cosy. It had everything that could be needed at a stay, from ironing board to hairdryer and a full length mirror! The little attention to detail made the whole difference to our stay. Would highly recommend using them as the experience was great throughout."
Ali 2-night trip
Posted 16 hours ago
The Conningbrook Hotel

Find out more about Sissinghurst

Everything you need to know about Sissinghurst holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sissinghurst holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Sissinghurst holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sissinghurst holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sissinghurst. 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 Sissinghurst holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sissinghurst holiday rentals we have selected for you start as low as €83 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sissinghurst rentals

At Expedia, we put the best Sissinghurst holiday 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 Sissinghurst 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 Sissinghurst holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sissinghurst. 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 holiday rentals in Sissinghurst?

Yes, there are holiday rentals close to the most popular sights in Sissinghurst, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Sissinghurst has to offer?

Fabulous 5 bed house with indoor swimming pool and hot tub in 1066 Country: This holiday home rental outside of Sissinghurst offers an indoor pool, a patio and laundry facilities to help you feel perfectly comfortable in your new surroundings. You can relax into your holiday with a garden and 1 hot tub.

What’s there to see and do in Sissinghurst?

Explore the area and family-friendly sights such as Hop Farm Family Park, or get out into nature at a spot like High Weald. Sissinghurst Castle and Garden and Balfour Winery are a couple of places you'll find in the wider area.

What’s a holiday rental in Sissinghurst like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sissinghurst. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family getaway.