Penshurst Place and Gardens which includes a fountain and a garden

Holiday rentals near High Weald

We found 2,074 holiday rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

December 2025

January 2026

If you'd like to stay close to High Weald, scroll through and discover holiday rentals to choose your home away from home. Whether you're staying in a holiday rental with your children or with friends, you'll have the amenities that you expect and more, such as parking and air conditioning. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - High Weald

Showing deals for:20 Mar - 27 Mar

Exceptional

(36 reviews)

16th Century Former Alehouse

Cranbrook

12% off

for 7 nights, 1 home

NZ$629 per night

includes taxes & fees

Exceptional

(5 reviews)

Beautiful re-imagined country chapel in peaceful hamlet

Otford

9% off

for 7 nights, 1 cottage

NZ$589 per night

includes taxes & fees

Exceptional

(5 reviews)

Winchelsea Coastal Holiday Home Close to Pool & Beach

Winchelsea

9% off

for 7 nights, 1 home

NZ$314 per night

includes taxes & fees

Pathway to main house, we are here if you need us for local knowledge, just ask.

Very good

(7 reviews)

The ‘Hidden Cottage’, a quiet country retreat, overlooking field s and gardens.

Mayfield, East Sussex

9% off

for 7 nights, 1 home

NZ$319 per night

includes taxes & fees

Heater indoor swimming pool - great all year rain or shine!

Exceptional

(36 reviews)

Heated indoor pool & spa, countryside holiday cottage near the beach & park

Hastings

30% off

for 7 nights, 1 cottage

NZ$348 per night

includes taxes & fees

Cottage view from within the gorgeous gardens & tennis court,

Exceptional

(16 reviews)

Charming Lavender Cottage with Gardens, Tennis & Family Fun

Yalding

28% off

for 7 nights, 1 cottage

NZ$444 per night

includes taxes & fees

Exceptional

(32 reviews)

Detached thatched cottage sleeping 2- 6 with its own luxurious hot tub

Kenardington

5% off

for 7 nights, 1 cottage

NZ$769 per night

includes taxes & fees

Cottages view from the tennis court & garden.

Exceptional

(26 reviews)

Gather & Unwind: Gardens, Woodlands & Tennis cottages.

Yalding

5% off

for 7 nights, 1 cottage

NZ$1,205 per night

includes taxes & fees

Exceptional

(35 reviews)

Luxury cottage sleeps 2 close to South Downs National park , coast and Goodwood

Thakeham

9% off

for 7 nights, 1 cottage

NZ$267 per night

includes taxes & fees

View of Flying Horse Cottage living room looking out to Decking platform

Exceptional

(33 reviews)

Rural Retreat with glorious views, I hour from London. 4* Gold Visit England

Nr. Tunbridge Wells

19% off

for 7 nights, 1 cottage

NZ$407 per night

includes taxes & fees

Exceptional

(27 reviews)

As seen in The Times 'Top 30 Cosiest Cottages in Britain' 2015

Westcott

9% off

for 7 nights, 1 home

NZ$986 per night

includes taxes & fees

Exceptional

(22 reviews)

Woodhouse Holiday Cottages, 3 Adjacent Holiday Lets . Ash Cottage

Henfield

14% off

for 7 nights, 1 cottage

NZ$325 per night

includes taxes & fees

Exceptional

(85 reviews)

Woodpeckers Cottage - One bedroom luxurious and Contemporary rural retreat

Sharpthorne

9% off

for 7 nights, 1 cottage

NZ$271 per night

includes taxes & fees

Exceptional

(45 reviews)

Beautiful cosy Rosebud Cottage in picturesque Steyning

Steyning

16% off

for 7 nights, 1 cottage

NZ$260 per night

includes taxes & fees

Cottage view from the tennis court — country charm at every serve.

Exceptional

(16 reviews)

Relaxed Rosemary Cottage Stay with Gardens, Tennis & Family Fun

Yalding

28% off

for 7 nights, 1 cottage

NZ$444 per night

includes taxes & fees

Exceptional

(27 reviews)

Sea View Studio Flat with heated indoor pool & spa, countryside location

Hastings

30% off

for 7 nights, 1 apartment

NZ$213 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in High Weald

High Weald

Find the best place to stay - High Weald

Tombreck 3 bed bungalow on private beach with direct access to sea

Sleeps 6 · 3 bedrooms · 1 bathroom

Welcome to Mafeking, a luxury holiday cottage in Benenden, Kent

Premier Host

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

Sleeps 6 · 3 bedrooms · 2 bathrooms

Stylish Luxury Let In Rye. Walk To Shops/Pubs/Restaurants + Near Beach

Sleeps 6 · 3 bedrooms · 1+ bathroom

Top rated rentals - High Weald

Premier Host

Beautiful cottage

Beautiful cottage. Friendly and efficient hosts. Quiet country setting.

Mary J.

Stayed Jun 2025

Premier Host

A beautiful and secluded retreat in the gorgeous Sussex countryside

We had a lovely stay at The Stables. The property is very comfortable, clean, and stylish in design. Lots of interesting history to the area. The hosts are great and extremely helpful and we arrived to snacks and a complimentary bottle of wine. We really enjoyed watching the wildlife which included a range of birds, bunnies, squirrels and the odd badger. Very reasonably priced and we would thoroughly recommend. Thank you!

Sue R.

Stayed Jun 2024

Our Escape to the Country

After 7 weeks on the road travelling around the UK, our stay in Pickle Cottage gave us a wonderful, peaceful break. We came to visit the gardens of Kent and found ourselves living in one right there. It was close to the lovely town of Tenterden and also central to access other well know sights in the area. The cottage is beautifully set up with everything we needed. We thoroughly recommend this property.

Alan and Jenny M.

Stayed Oct 2023

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

More holiday ideas

Holiday Rentals

Holiday rentals near High Weald

Holiday rentals with weekly discounts - High Weald

Image gallery for 16th Century Former Alehouse

16th Century Former Alehouse

Find spaces that suit your style

Find properties near top attractions in High Weald

Map Attractions

High Weald

Find the best place to stay - High Weald

Tombreck 3 bed bungalow on private beach with direct access to sea

Top rated rentals - High Weald

Beautiful cottage

Peace of mind

More quality time

All the privacy of home

More for less

More holiday ideas