
Vacation rentals in Chelsham
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Top-rated vacation rentals in Chelsham
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Convenient Caterham Bolt Hole near Gatwick/London
We have 2 delightful, and newly-renovated double rooms plus shower room at semi-basement level. ‘Below Stairs’ has its own entrance so you have full privacy away from the busy family life going on upstairs! The accommodation is a perfect place to lay your head for a weekend, a work trip or accommodation around a wedding or event. There’s no kitchen although tea and coffee are provided and the nearby Caterham Cafe does a great breakfast! Costa, Cafe Nero and restaurants are also moments away.

A luxurious country retreat with Jacuzzi hot tub
A unique and luxurious retreat set alongside a historic 13th Century Wealden hall house Your private countryside haven- a beautifully designed contemporary hideaway for two offers rare privacy and indulgence. Nestled in one of the most magical and peaceful corners of Kent. Heritage meets luxury, where the charm of medieval England blends effortlessly with refined comfort. Surrounded by rolling Wealden countryside and some of the finest traditional pubs in the country. Relax and unwind in style.

Gorgeous annex in Surrey, near to Caterham School
Luxury annex bristling with light, part of a beautiful house set in half an acre of garden with pond and trees. Located in a semi rural setting, just off the North Downs in leafy Chaldon, with the rolling Surrey Hills on your doorstep. 1 mile to Caterham town centre. Perfect for a family passing by the area or while moving homes/building renovations. Great for Caterham school visiting parents. Direct access to Central London in less than 1 hour, Gatwick Airport in 20 minutes, 5 min to the M25.

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.

Lavish Retreat & Champagne 30mins Taxi from London
The Little Touch of Grey, provides an electric ambiance and the perfect setting for the elite of mind, who wants to reward both themselves and their partner. We are proud to share the latest addition to our portfolio with those who appreciate of all things bespoke. Included are; a complimentary bottle of Champagne, indoor & outdoor Jacuzzi, underfloor heating, sound system and salacious yet tasteful surprises throughout. For special occasions, use our secret compartment to add to your surprise.

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.

Taylour House - Historic, unique, yet modern
Welcome to our historic 'hidden gem' Taylour House built in 1468 for the Lord Mayor of London. Quiet yet town centre location with local amenities on your doorstep. Easy reach of Central London, (Edenbridge Town station 10 mins walk) Gatwick and Heathrow. Sleeps up to 10 guests. Private dining by prior arrangement. Perfect for a holiday, family gatherings, birthday celebrations and hen/stag and bridal parties. Full refurbishment carried out in 2023. Children and dogs very welcome.

Where Country meets Suburbs
Situated in the picturesque countryside of Warlingham, there is something for everyone; a variety of pastimes that will appeal to that naturistic inner being and or a well-deserved relaxing break. Close to Biggin Hill Airport and London Gatwick Airport. Easy access to London. Central to four Golf Clubs in the area. Various dinning options, including the famous White Bear Gastro Pub (2 min walk). See the history of Charles Darwin and visit his house. Walking and cycling trails, and Much More!

The Little House Self contained woodland setting
Enjoy the lovely setting of this romantic spot set in woodlands, surrounded by nature and wildlife. On site is a yoga studio with classes available to book or free use of the studio for personal practice when available. With good public transport links to East and West Croydon, from there be in Central London within the hour for shopping, theatre, museums and night life. Locally we have a good selection of restaurants and bars. Nearby you will find a hair salon, newsagent and beauty salon.

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

Twilight Retro Haven + Hot Tub + Garden Cinema
Step into Kooringa, an Asian-inspired retro haven in Warlingham, Surrey. This stylish retreat offers a luxurious hot tub, a garden cinema for magical movie nights, and stunning countryside views. Just 10 minutes from Upper Warlingham Station (direct to London in 30 mins), it's perfect for couples or small groups. Explore local gems like Surrey Hills, enjoy the secluded garden, and unwind in retro-modern comfort. Your idyllic escape, just a short journey from city life, awaits!

Historic Surrey Hills Cottage 30 mins from London
Step inside a piece of English countryside history. Elmore Pond Cottage in the village of Chipstead in the Surrey Hills Natural Landscape, with London just thirty minutes away by train and 15 minutes to Gatwick Airport. Sleeps up to six across two double bedrooms and a sofa bed, wake to views across the Surrey Hills, wander through the kitchen garden, and end the day at our lovely local pubs.
Popular amenities for Chelsham vacation rentals
Other great vacation rentals in Chelsham

Idyllic new build,2 bedroom cottage

Keston. Pretty Cottage, 2 double bedrooms and view

School Cottage conversion

4BR Sleeps 8 & Garden Flat En-suite Large & WiFi

Snuggle Inn -Group Stays- Parking - Free Gym- M25

Elegant One Bedroom Flat 30 min Central London /TV

Superb Studio flat in South Croydon, London

Modern Flat - Spacious & Comfy
Destinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- London Bridge
- Brighton Seafront
- The O2
- ExCeL London
- Emirates Stadium
- Tower Bridge
- Clapham Common
- Goodwood Motor Circuit
- Thorpe Park Resort
- Buckingham Palace
- Chessington World of Adventures Resort
- Alexandra Palace
- South Downs National Park
- London Stadium
- Big Ben
- Victoria Park
- Windsor Castle
- LEGOLAND® Windsor Resort





