Holiday rentals in Westerham

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Top-rated holiday rentals in Westerham

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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
4.99 out of 5 average rating, 137 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
A well-maintained garden is framed by lush greenery, showcasing vibrant flower beds and neatly trimmed hedges. Beyond the garden, expansive views of rolling hills and the Darent Valley can be seen under a partly cloudy sky.
Apartment in Otford
4.99 out of 5 average rating, 170 reviews

Amazing Views over Garden & Valley

Wake up & lift the automatic blinds directly from your SUPER KING SIZE BED & be captivated by the VIEW of the beautiful Darent Valley unfolding before you through the picture windows. SNUGGLE in a cosy armchair with a book, listen to your favourite music or EXPLORE many footpaths along the valley. Stroll through the fields to Otford & Shoreham villages, visit HISTORIC HOUSES & vineyards or simply stay at home & enjoy a spacious studio apartment whilst staring at the sunset with a glass of wine

Top guest favourite
Two wooden lounge chairs are positioned on a stone patio, offering views of the expansive greenery and rolling hills in the distance. Lavender plants line the edge of the patio, enhancing the serene rural setting.
Cottage in Sevenoaks Weald
4.99 out of 5 average rating, 104 reviews

Quiet luxury rural cottage with fantastic views.

Rare, peaceful and spacious newly built cottage with private garden, comfortably sleeps 6. On Greensand AONB escarpment, with spectacular uninterrupted views over the Kent countryside. Rural retreat 2 miles south of Sevenoaks, half an hour by train to London Bridge. On private road. Own access and parking. New kitchen with light and airy dining and sitting area. WiFi. Very private south facing garden and patio. Fantastic walks to local pubs, national trust, great cycling. Use of tennis court.

Guest favourite
The Summerhouse features a charming wooden exterior with a sloped roof and large glass doors. Surrounded by lush greenery, it includes a small seating area on the patio for outdoor relaxation, inviting nature into the living space.
Guest house in Surrey
4.95 out of 5 average rating, 585 reviews

SUMMERHOUSE luxury smart barn, projector 75Mb WiFi

The Summerhouse is a modern barn conversion located on the Flagpole Cottage estate with the main house dating back to 1650 in quaint and friendly Tandridge Village. The Summerhouse has a private entrance with magnificent views over the country side from the floor to ceiling windows, yet only 20 miles from London. Open plan living with sleeping arrangements on the mezzanine and ground floor sofa bed. WiFi (75Mb fibre) and secure parking (24/7 outdoor CCTV) is free. Private terrace on the back.

Guest favourite
Cabin in East Sussex
4.97 out of 5 average rating, 115 reviews

Goldcrest Lodge Wadhurst

Goldcrest Lodge is a peaceful hideaway within secluded woods on the 140 acre historic estate of Wadhurst Castle. It is designed to blend in to its woodland setting, yet is bright and spacious with modern luxuries - perfect for a romantic break, a restful escape or for reconnecting with nature. It has a double bedroom (5' bed) with huge picture window, a central main room with sofa bed leading to a kitchen area and separate shower room beyond. Decking and private screened bath. Dog friendly.

Top guest favourite
The image captures an aerial view of a charming Tudor property surrounded by lush greenery. Two distinctive white-tipped oast houses are prominently displayed, along with neatly manicured gardens and open spaces. The serene countryside landscape extends into the background, showcasing rolling hills.
Home in Ide Hill
4.96 out of 5 average rating, 333 reviews

Oast Farmhouse, Ide Hill, Hever, Edenbridge

The Oast House is on a private Tudor Estate. A listed mid-Victorian property has charming period features, a large garden and storage. It theoretically sleeps 10 but suitable for 7 if one prefers sleeping alone. Terrific for group bookings, cycling and triathlon participants, temp workers, golfers, extended families in area for special occasions, corporate charity rides, or bake off weekends! Perfect for visiting Tudor England all around beautiful West Kent. We are 35 mins from South London

Top guest favourite
The spacious bedroom features a comfortable bed dressed in soft linens, flanked by bedside tables with lamps. Exposed wooden beams create a rustic ambiance, while patterned curtains frame the window. A wooden dresser adds character, and a full-length mirror reflects the room's charm.
Barn in Horley
4.94 out of 5 average rating, 533 reviews

Cosy, Rustic 17th Century Country Barn.

Charming 17th century Barn conversion. Restored with every attention to detail, abundance of character & exposed beams, fully equipped kitchen, attractive bathroom with roll top bath & rain shower. Underfloor heating, High Speed Wifi, Smart TV and optional hot tub (please enquire and book in advance). Just 14 minutes from Gatwick Airport/Station & the Express into London takes only 30 minutes, yet the Barn is set in open countryside, surrounded by fields, on an Equestrian property

Guest favourite
A spacious barn-style home is showcased against a clear sky, featuring a stone façade and large windows. A grassy lawn extends in front, with shadows cast by trees. Outdoor seating is positioned on a patio area, and a swing set is visible in the background.
Barn in Milton Street
4.94 out of 5 average rating, 203 reviews

Beautiful barn on the South Downs Way

Beautiful barn, perfect for walkers, also great as a comfortable and spacious base for exploring the local countryside. Local cultural attractions include Glyndebourne, Drusilla's Park, South Downs Way. This spacious artist's home is located right on the South Downs Way, and it is only about an hour and a half walk to the coast at Exceat. There is a tree house for kids, a couple of swing seats for chilling out on, and the Cuckmere runs through the bottom of the garden.

Top guest favourite
Guest suite in Brasted
4.96 out of 5 average rating, 113 reviews

Charming Guest Suite in the Kent Countryside

Our private annexe is nestled in a peaceful cul-de-sac, just 3 miles from Chartwell and 4 miles from Sevenoaks. London Bridge is a convenient 30-minute train ride away. Enjoy high-speed WiFi, HDTV, and a well-equipped bathroom. Refreshments like coffee, tea as well as an assortment of snacks are provided for our guests. The High Street, local pub, and shops are within walking distance. Guests can park their car on-site for free. EV charging available at extra cost.

Top guest favourite
An aerial view showcases the unique geo dome structure surrounded by lush greenery. A wooden deck leads to an outdoor seating area, fire pit, and hot tub. The tranquil setting emphasizes a peaceful retreat in nature.
Dome in West Horsley
4.94 out of 5 average rating, 380 reviews

Unique Dome | Glamping | Hot Tub | Surrey | Adults

Olive Pod is the ultimate cosy, private and picturesque geo dome retreat. Set on a fruit farm in Surrey, in its own secluded field behind tall fir trees, with no other pods or tents nearby. A firm favourite adults-only escape for proposals, anniversaries, birthdays and honeymoons - we can also decorate for your arrival ✨ The perfect place to unwind and recharge in a peaceful natural setting. Ideal for couples or friends. No infants, children or pets.

Top guest favourite
Bungalow in Kent
4.97 out of 5 average rating, 100 reviews

Luxury Spa Retreat: Sauna & Hot Tub

Escape to our exclusive gated spa retreat, nestled on 5.5 acres of serene countryside in picturesque Fawkham, Kent. This private and tranquil haven offers breathtaking views of rolling hills, perfect for relaxation. Unwind in the luxurious sauna, steam room, or hot tub, soaking in the peace after exploring local attractions. Just minutes from Brands Hatch, our retreat blends seclusion with convenience, your ultimate quiet getaway awaits.

Top guest favourite
A charming thatched cottage is surrounded by meticulously maintained gardens featuring geometric hedges and a stone pathway. Lush greenery and trees frame the scene, while a tranquil pond reflects the clear sky above.
Cottage in Rotherfield
4.98 out of 5 average rating, 351 reviews

The Granary, Organic Vineyard stay with Pool.

Coes Farm offers 50 acres of absolute tranquillity in amongst nature, with a bit of luxury thrown in too! We have formal gardens and ornamental ponds, a large lake, plenty of woodland, open fields, an indoor saltwater swimming pool with hot tub, a tennis court and a games room which is resident in our Micro-Winery! We planted our 5 acre vineyard in Spring 2021 and extended the existing Orchard with cider varieties in 2023.

Popular amenities for Westerham holiday rentals

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  4. Kent
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