Holiday houses in Chelsfield

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Top-rated holiday rentals in Chelsfield

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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.
Condo in Otford
4.99 out of 5 average rating, 155 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
A cozy lounge area is featured with a spacious sofa and two modern armchairs arranged around a low wooden coffee table. A window allows natural light to brighten the space, while a decorative rug complements the wooden ceiling beams and gentle colour palette.
Cottage in Greater London
4.92 out of 5 average rating, 102 reviews

Gingerbread House in a quiet woodland setting

Gingerbread House is a self-contained annex set within the owners property, bordered by bluebell woodland and arable fields. The house is ideally situated for day trips into central London by train, many National Trust and English Heritage sites in Kent/Sussex, or events at Brands Hatch. The village of Pratts Bottom and the local pub is within a 10 minute walk. The nearest train stations are a 10 mins drive and offer fast services to London Charing Cross on the Tunbridge Wells/Hastings line.

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.
Guesthouse in Surrey
4.95 out of 5 average rating, 570 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.

Top Guest favourite
Shepherd’s hut in Headley
5 out of 5 average rating, 390 reviews

Secret Lodge: shepherds hut with hot tub & sauna

Stay in a luxury shepherds hut in the stunning Surrey Hills, only an hour from London. A perfect couples escape with a beautiful hot tub under the trees and a wood fired sauna experience bookable as an optional extra. We are located near Box Hill so you can enjoy countryside walks with spectacular views and visit some lovely local gastropubs. We are dog friendly for an extra fee. We supply a variety of grazing platters too. The perfect stay for birthdays, anniversaries and special nights away!

Top Guest favourite
Cabin in Rochester
4.96 out of 5 average rating, 460 reviews

Cosy Rural Retreat with Log Burner

The Snuggery is a converted outbuilding that has been set up for a cosy stay with a wood burning stove and lots of snuggly wraps to cuddle up in. The open plan interior, high vaulted ceilings and natural oak flooring create an interior which is fun, light and airy. Walking enthusiasts will enjoy walks from the back door straight on to the North Downs Way and there is a bench by the front door fitted with a heated element, perfect for warming up your walking boots. Photos by Chloe-Rae 

Top Guest favourite
A charming cottage exterior is depicted, featuring a combination of whitewashed walls and earthy wooden elements. The slate roof is adorned with warm wooden shingles. A small, well-maintained shrub adds greenery to the entrance, alongside a wooden door framed by an inviting porch.
Cottage in Kemsing
4.94 out of 5 average rating, 228 reviews

Comfortable & cosy 17th century Listed Cottage.

The cottage is in a semi-rural setting. There is a garden with table and chairs for sitting outside, and a BBQ to enjoy summer days. The cottage has everything to ensure your stay is comfortable. Nearby there is a choice of quaint country pubs and the bars and restaurants of Sevenoaks are a short drive. There are lots of wonderful nearby country walks. Hever Castle, Chartwell House (Winston Churchill), & Down House (Charles Darwin) are just some of the attractions within a short drive.

Top Guest favourite
A tranquil outdoor area is surrounded by rustic wooden walls and beautiful greenery. Comfortable seating is arranged around a table, with pots of plants adding color. Wisteria drapes elegantly from above, creating a serene setting that is inviting for relaxation.
Barn in Chiddingstone Causeway
4.98 out of 5 average rating, 166 reviews

Charming barn conversion in the Kent countryside

Barneta is the annex of a converted barn and is set in an idyllic spot on a sheep farm in the heart of the Kentish countryside but only 10 minutes drive from Hildenborough train station with trains to London and the South Coast. All the amenities of Royal Tunbridge Wells are 20 minutes drive away. It is an excellent base for walking and there are many places of interest to discover such as Penshurst Place, Chiddingstone and Hever Castles with fantastic local pubs along the routes.

Guest favourite
A charming cottage is set against a clear blue sky, featuring a pitched roof and two gabled dormer windows. Flowering plants and green grass frame the inviting entrance, highlighting the cottage's warm yellow door and brick exterior.
Cottage in Kent
4.96 out of 5 average rating, 210 reviews

Cosy Private Cottage in Wrotham, Kent Downs AONB

Set on the edge of Wrotham village in the Kent Downs Area of Outstanding Natural Beauty. This self contained one bedroom cottage comes with free off street parking and use of a large cottage garden. We welcome well behaved dogs. A two minute walk into Wrotham Village, with a picturesque church, village shop, and three pubs including the AA Rosette awarded Bull Hotel. Now with a newly completed private patio to the rear solely for guest use. Dog secure with high gate.

Superhost
Apartment in Greater London
5 out of 5 average rating, 3 reviews

Palm Tree House - Winter Wonderland

You will absolutely love this themed studio that can host up to 4 people. Enjoy modern furnishings, a fully equipped kitchen with a washing machine and dishwasher, a spacious bathroom with a shower, and a comfy bed and sofa bed. Take advantage of Free Parking, super-fast Wi-Fi throughout, Smart TV. Free access to the shared GYM and WORKSPACE. It is just minutes from Orpington station, with easy access to London. POTENTIAL FOR NOISE, READ BELOW.

Top Guest favourite
A spacious living area showcases wooden beams and an open layout. A comfortable sofa faces a wood-burning stove, with a flat-screen TV nearby. The dining table is surrounded by woven chairs, and large windows provide natural light while offering views of the entrance and surrounding nature.
Cottage in Marden
4.99 out of 5 average rating, 588 reviews

The Lodge

**Opted in to Airbnb's enhanced cleaning protocol** Cosy barn-style accommodation nestled in the heart of the Kent countryside. Located close to National Trust sites and country walks. The Lodge is the perfect country getaway and romantic retreat. Please note this is strictly a NO SMOKING property inside the Lodge, the garden and surrounding field. The property is also NOT SUITABLE for infants, children or pets. Two adults only.

Top Guest favourite
The bedroom features a plush kingsize bed with soft linens and an inviting assortment of pillows. Warm gray paneling surrounds the bed, complemented by stylish bedside tables with lamps. Natural light enters through a skylight, adding brightness to the cozy space.
Cottage in Plaxtol
5 out of 5 average rating, 272 reviews

Exquisite Cottage in Beautiful Kent Countryside

This delightful cottage has been lovingly refurbished and offers a luxurious, yet cosy and comfortable space for the perfect weekend getaway. Located in a designated Area of Outstanding Natural Beauty, we are situated in the heart of our pretty village surrounded by miles of beautiful Kent countryside. A beautiful spot to indulge in countryside walks and delicious pub lunches.

Guest favourite
A charming converted coach house is depicted from the exterior, showcasing a brick façade with distinctive architectural elements. A gravel driveway leads to the entrance, surrounded by well-maintained greenery and wooden fencing, creating an inviting approach to the property.
Guest suite in Kent
4.93 out of 5 average rating, 369 reviews

A Kent Coach House getaway for peace and quiet

Come and enjoy a restful getaway in your private wing of our characterful converted coach house. Nestled in a peaceful hamlet, you'll be able to explore the North Downs AONB from your own front door, while still being in easy reach of London and the coast. Well behaved dogs welcome. We're looking forward to welcoming you to our Kentish family home soon.

Popular amenities for Chelsfield holiday rentals

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