Family-friendly holiday rentals in Wealden

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Top-rated family-friendly rentals in Wealden

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
A shepherd’s hut is positioned in a grassy area, with wide doors open to the exterior. An alpaca is seen grazing on the lawn, surrounded by lush greenery under a clear blue sky. Outdoor seating is visible nearby, inviting relaxation in nature.
Shepherd’s hut in East Sussex
5 out of 5 average rating, 132 reviews

The Woolly Retreat - Alpaca Shepherds Hut.

Nestled in a secluded Alpaca field in the heart of the enchanting Ashdown Forest lies a cosy, new Shepherd’s Hut in the idyllic village of Hartfield, famous for its connection to Winnie the Pooh and his timeless adventures. Surrounded by Alpacas which you can feed , this charming retreat offers a perfect blend of rustic luxury & nature. Whether you're looking for a romantic getaway, or just a relaxing weekend immersed in nature, our shepherd's hut is the place to unwind, recharge and reconnect.

Top guest favourite
The oak-framed cottage is set against a clear blue sky, showcasing solar panels on the sloped roof. A spacious lawn surrounds the building, and wooden patio furniture is visible on the sunlit terrace, inviting outdoor relaxation.
Home in Heathfield
4.9 out of 5 average rating, 367 reviews

Jacks Cottage -

A beautiful oak framed building with great views of the south downs. Accommodation comprising of a comfortable lounge with TV and wifi and log burner. The kitchen is well equipped with a dishwasher, oven and microwave. One double bedroom downstairs with en suite shower room. Upstairs there is a mezzanine with two single beds and a sitting area above the lounge area with a bathroom with free standing bath. The outside space is a south facing patio with table and chairs and a BBQ is available.

Top guest favourite
Guest house in East Hoathly
4.94 out of 5 average rating, 165 reviews

‘The Water Snug’ Beautiful Floating Cabin

Romantic lake cabin for two, floating on our peaceful one-acre lake in ancient woodland. Relax by the cosy log burner, cook in the fully fitted kitchen, and wake to magical lake views from the bedroom. In spring, enjoy the woodland with bluebells and delicate flowers; summer brings long golden evenings over the lake, and autumn paints the trees in rich, vibrant colours. Step outside to gentle ripples, watch wildlife, or visit East Hoathly village with its café, shop, and pub just minutes away.

Guest favourite
A charming treehouse, built from cedar wood, is nestled among lush greenery. The structure features a conical roof and large, arched windows. A wooden boardwalk with steps leads to the entrance, surrounded by vibrant leaves and natural scenery.
Treehouse in Mayfield
4.99 out of 5 average rating, 142 reviews

Luxurious, picture-perfect, stunning treehouse

Hoots Treehouse is a picture-perfect, romantic, luxurious treehouse with all mod cons in an area of outstanding natural beauty - only 45 minutes south of M25. Clad in aromatic cedar wood, beautifully furnished - ideal private, woodland retreat for couples. Can also comfortably sleep up to 2 children (from 5 years) on single mattresses in loft area accessed by a ladder and hatch. NOT SUITABLE FOR 4 ADULTS. A wonderful place to chill-out and lose yourself - you won't want to leave! Sheer bliss!

Guest favourite
The off-grid cabin is set within an open meadow, surrounded by trees and open fields. The structure features large windows, allowing ample natural light inside. Outdoor seating is present, creating an inviting space for relaxation in nature.
Tiny home in Whitesmith
4.94 out of 5 average rating, 101 reviews

Romantic Off-Grid Tiny Home Ft Beachy Head Hike

Escape the noise. Reconnect with nature. Our cosy off-grid cabin, Hwin, is set in an open meadow with sweeping countryside views and zero light pollution (perect for stargazing!) Fully off-grid, but with all the comforts: hot shower, king-size bed, full kitchen, and a wood-burning stove. - Panoramic views from bed - Dog-friendly with outdoor space to roam - 1km walk to the Six Bells pub (proper pub) - 3km from Gun Tap Room & Brewery - 30 mins to the Beachy Head to Seven Sisters coastal hike

Guest favourite
Rooftop space is equipped with a circular hot tub and several wooden chairs with cushions. Soft lighting from string lights creates a relaxed ambiance, while the surrounding trees and open field provide a natural backdrop.
Tiny home in Furner's Green
4.88 out of 5 average rating, 108 reviews

Delightful Double Decker Bus with Hot Tub sleeps 4

Unique Stay in a fabulous converted DOUBLE DECKER BUS! Unwind in the rooftop Hot Tub after a day of wandering the Bluebell Woods, playing Crazy Golf on site, exploring the nearby Ashdown Forest or the local Vineyard for Wine Tasting or enjoying the onsite Ice Cream parlour. The bus boasts a super comfy double bed downstairs and European sized bunks up top! Heating upstairs & Down, as well as heated blankets to keep it nice and cozy in the colder months! Over 16s ONLY June through August

Guest favourite
Barn in Hellingly
4.91 out of 5 average rating, 198 reviews

The Barn, Hot tub, projector, Fire Pit, Pizza oven

Our Grade ll Barn is in a quiet countryside spot within driving distance of Eastbourne, Tunbridge Wells, Brighton and Hastings. This unique place has a style all of its own. A spacious home for a romantic getaway or a weekend adventure exploring the local beaches, walks & golf clubs The Barn is equipped with a hot tub, outdoor cinema screen, Ooni pizza oven, firepit/BBQ. We have a driveway which has space for two cars directly outside. *Please note our place is NOT suitable for children.

Top guest favourite
The exterior of the converted barn features a sloped roof with rustic shingles and wooden siding. A gravel driveway leads to the entrance, flanked by planters. Large windows offer views into the open interior, while trees provide a natural backdrop.
Barn in East Sussex
4.97 out of 5 average rating, 273 reviews

The Cart Lodge a cosy rural hideaway

Situated in a secluded part of our 16th century farm, this detached, south facing cart barn has been converted to a very high standard. In an ideal location overlooking a large duck pond and with distant views to the South Downs. It is a great base for walking the Wealdway or cycling the Cuckoo Trail. Places to explore include Lewes and Eastbourne, 9 miles. Glyndebourne 6 miles. An excellent pub and restaurant is within a ten minute walk along country footpaths. The village shop 2 miles.

Top guest favourite
A private patio area is furnished with gray seating and a black metal coffee table. Surrounding the space, greenery and flowering plants create a serene environment, complemented by a decorative mirror reflecting the outdoor light.
Home in Buxted
4.99 out of 5 average rating, 184 reviews

A deluxe home to explore Sussex and beyond

This deluxe, dedicated two-bedroom accommodation is light, fresh and airy. A great base to relax in the garden and games room or explore Sussex, Kent and beyond. Situated is in a quiet cul-de-sac with lovely country walks on your doorstep. Also you are within easy driving distance of Ashdown Forest, the South Downs the coast, the Bluebell Railway and several National Trust properties. Buxted train station, offers easy access for shopping in the local town and is a direct line to London.

Top guest favourite
The rustic shepherd's hut features a dark wooden exterior with pale blue doors that open to a welcoming entrance. A small wooden staircase leads to the door, flanked by potted flowers. A cozy chair is positioned just inside, suggesting a comfortable retreat.
Shepherd’s hut in Ringmer
4.92 out of 5 average rating, 273 reviews

Blackbird shepherds hut

Blackbird Shepherds Hut is nestled on a rural estate, away from the bustle of the South East, just an hour from London. A natural habitat for wilderness. The spectacular landscape, dark night skies and breath-taking wildlife provide a truly inspirational escape. It is a very special place, handmade by the owners and full of artistic charms which provide an idyllic setting for a weekend escape or simply to immerse yourself in nature and have time to hear the dawn chorus and the owls.

Guest favourite
A charming chalet-inspired studio barn is surrounded by lush greenery, featuring wooden exterior siding and a gently sloped roof. Sunlight filters through the trees, illuminating the inviting entrance and the landscaped garden area in front.
Guest house in Buxted
4.95 out of 5 average rating, 860 reviews

Stunning Studio Barn, Buxted

Our chalet-inspired studio barn, with vaulted ceilings and oak beams, is light and airy in the summer and beautifully warm and cosy in the winter, with underfloor heating throughout. It is completely self-contained, with a separate entrance from the adjacent family house. With a sumptuous superking bed (or two twins), sofa bed, unlimited fast WiFi and HDTV, you are assured of a relaxing and welcoming stay in a family-friendly setting in the East Sussex countryside.

Top guest favourite
The exterior of the eco-friendly cottage is framed by an array of flowering plants and gravel pathways. Natural wood cladding complements the blue sky. Outdoor seating includes a dining table and chairs, inviting relaxation in the spacious garden area.
Cottage in Brightling
5 out of 5 average rating, 165 reviews

The Long Stable: Rural haven, spacious, fast Wifi

Stylishly fitted and eco-friendly, our detached, self-contained cottage is in a very rural location. There are no other holiday cottages on the farm. Situated in the High Weald Area of Outstanding Natural Beauty, on a sheep farm of 23 acres (which you are free to roam), this is a real get-away-from-it-all location. One of the most peaceful and relaxing places you will ever stay. With underfloor heating and a wood-burning stove you will be cosy whatever the weather.

Popular amenities for Wealden family-friendly rentals

When is the best time to visit Wealden?

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Avg. price$224 SGD$222 SGD$234 SGD$257 SGD$268 SGD$273 SGD$292 SGD$299 SGD$274 SGD$263 SGD$249 SGD$294 SGD
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Quick stats about holiday rentals that are family-friendly in Wealden

  • Total holiday rentals

    Explore 1,300 holiday rentals in Wealden

  • Nightly prices starting at

    Wealden holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 57,690 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 580 rentals that welcome pets

  • Holiday rentals with a pool

    100 properties feature pools

  • Rentals with dedicated workspaces

    590 properties have a dedicated workspace

  • Wifi availability

    1,250 of Wealden holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wealden rentals

  • 4.8 Average rating

    Wealden stays are highly rated by guests – averaging 4.8 out of 5!

  • Nearby attractions

    Wealden’s top spots include Drusillas Park, Bewl Water and Bateman's

Destinations to explore