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Sissinghurst Vacation Rentals

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Check prices for these dates

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

Our top choices for Sissinghurst vacation 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 CA $418
CA $418 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $381
CA $381 total
includes taxes & fees
Oct 22 - Oct 23
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 CA $401
CA $481 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $346
CA $346 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $381
CA $381 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $381
CA $381 total
includes taxes & fees
Oct 22 - Oct 23
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 CA $127
CA $193 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $360
CA $360 total
includes taxes & fees
Oct 22 - Oct 23
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 CA $266
CA $266 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $1,383
CA $1,383 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $282
CA $387 total
includes taxes & fees
Oct 22 - Oct 23
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 CA $196
CA $264 total
includes taxes & fees
Oct 22 - Oct 23
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 CA $109
CA $131 total
includes taxes & fees
Oct 23 - Oct 24
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 CA $325
CA $391 total
includes taxes & fees
Nov 21 - Nov 22
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 CA $601
CA $722 total
includes taxes & fees
Oct 31 - Nov 1
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 CA $381
CA $381 total
includes taxes & fees
Oct 22 - Oct 23
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 CA $216
CA $265 total
includes taxes & fees
Oct 22 - Oct 23
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 CA $370
CA $370 total
includes taxes & fees
Nov 5 - Nov 6
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 CA $1,128
CA $1,128 total
includes taxes & fees
Oct 30 - Oct 31
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 CA $987
CA $987 total
includes taxes & fees
Nov 6 - Nov 7
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 13 hours ago
The Conningbrook Hotel

Find out more about Sissinghurst

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sissinghurst. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Sissinghurst?

Yes, there are vacation rentals near top sights in Sissinghurst, or you can choose a more remote option if you'd like a relaxing place to stay.

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

Fabulous 5 bed house with indoor swimming pool and hot tub in 1066 Country: Visitors like this Sissinghurst vacation home rental. It offers an indoor pool, a patio, and laundry facilities to help you feel perfectly comfortable in your new surroundings. You can relax into your vacation with a garden and a 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 larger area.

What’s a vacation rental in Sissinghurst like?

Vacation rentals are privately owned properties where you can stay for a long or short time in Sissinghurst. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip.