
Holiday houses in Chessington
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Top-rated holiday rentals in Chessington
Guests agree: these stays are highly rated for location, cleanliness and more.

Luxury Woodland Shepherds Hut & Romantic Hot Tub
Escape to your own little bit of luxury in the stunning Surrey Hills, conveniently about an hour from London, and stay in one of our two gorgeous shepherd's huts. We are located near the village of Headley near Box Hill, so you can enjoy beautiful countryside walks, whilst staying in a luxury hut with modern facilities like high speed wifi! Dog friendly (extra fee). We have a wood fired couples hot tub and can supply grazing platters, perfect for birthdays, anniversaries and special nights away!

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.

Ground floor studio with private entrance
A quiet, ground floor studio flat, fully self-contained, affording high levels of privacy & comfort, with freedom to come & go via your own front door at anytime day or night. Situated in a quiet, safe, leafy cul-de-sac in Cobham (dubbed UK’s Beverly Hills!) which offers: The Ivy, gastro pubs, boutique shops, Waitrose & more. Driving: 5mins to Oxshott station, 10mins to M25, 20mins to Guildford (or train). Airports: Heathrow (10miles), Gatwick (16miles). Trains to London Waterloo: 35mins.

Beautiful oak barn in peaceful countryside setting
Delightful detached barn crafted from French oak in a peaceful private lane on a gated country estate. Luxuriously appointed with full facilities for a short break or longer stay. Air Con. Free EV charging point. Many public footpaths close by. Local shops are only a 10 minutes stroll. Gastro pubs, restaurants and independent shops within easy walking distance. A short drive from M25 (J11). Fast rail links to London from Woking. LGBTQ+ friendly. Friendly Spaniel and Siamese cat on site.

Self-contained, double bed, clean and comfortable
Please read. A comfortable, clean uncluttered standard double bed annexe with en-suite, kitchenette and sitting room looking out onto the garden in a residential road, for 'single occupancy' only. NB. the annexe is not a 'day/holiday sanctuary' as life continues around it during the busy working day within a residential road. Most suitable for those working (regular hours) in the area as guest will be required to vacate the property daily between the hours of 11.00-16.00 or thereabouts.

Studio, own access, self contained.
The room has it's own entrance door. It has a double Queen size bed, shower room and kitchen area (tea, coffee, cereal etc supplied) with fridge, microwave and single induction hob. There is a sofa, TV & table with two chairs. Our home is about a 15 minute walk to Claygate station. Trains direct to London Waterloo (35 mins) and Guildford. Claygate has local shops and a CoOp, several pubs and restaurants and we are close to a bus stop with a frequent bus service to Kingston for major shops.

Peaceful & cosy detached annex with outdoor space
Situated within the grounds of a private property, set back from the road in a leafy residential part of Epsom. Welcome to our peaceful, detached annex offering flexibility, comfort and outdoor space. International guests will find us conveniently situated within 30mins drive of London Gatwick and Heathrow Airports (traffic permitting) and 40mins by train into central London. Ideal for those needing a base to enjoy the delights that Surrey has to offer or somewhere quiet to work from.

London & Surrey Cub House
Your own private stylish cabin, own entrance, self check-in. King-size bed, en-suite, kitchenette & private outside space. 8min walk to 2 stations into central London (Waterloo 25min, Wimbledon 15min). Good links to Hampton Court, Kingston upon Thames, Surrey walks and villages. Superloop 7 Bus (SL7) direct to and from Heathrow Airport, 1hour. Very quiet residential road with free parking. No more than 2 guest permitted at anytime on the property. No smoking/vaping on the property.

Hampton Court: Spacious, Bright & Tranquil Annexe
Our newly renovated spacious 2 bedroom annex is situated in a wide tree lined road, a premier location just a few minutes walk away from the charming cafés, shops and restaurants of Hampton Court Village, Hampton Court Palace and local train station. Adjacent to but detached from our elegant Victorian family home, this bright and stylish space is tranquil and self contained and enjoys additional benefits of a private south facing patio garden and dedicated off street parking space.

Quaint Self-contained Loft Studio nr Hampton Court
Quaint, quirky, clean and bright for you to relax in private, coming and going as you wish. Nestled in a safe, quiet area, perfectly situated for Hampton Court, Sandown Park Racing, Wimbledon Tennis, Bushy Park with its wild deer, the Thames and great shopping in Kingston. Breakfast included with pubs and restaurants nearby. Within walking distance of two railway stations, direct into London. Twickenham Stadium is just under 30 minutes away. Plenty of free on-street parking.

Self Contained Cottage in Thames Ditton Village
Beautiful self contained 1 bedroom cottage in the grounds of one of Thames Ditton’s oldest properties. Superbly located next to the river with pubs, restaurants, coffee shops, and village stores close by. Thames Ditton is a pretty village located close to Hampton Court, Surbiton, and Kingston Upon Thames and 30 minutes by train to London Waterloo. Go Boat hire is a minutes walk and the slipway to the Thames is opposite the house if you have your own paddle board/canoe.

The Hampton Court Hideaway
The Hampton Court Hideaway is a peaceful and relaxing guesthouse (converted detached double garage). Beautifully designed to a very high standard and powered by renewable energy. The property comes with a fully equipped kitchen, bathroom with walk in shower, 2 double beds (2nd on mezzanine) and one sofa bed upon request. We also have an EV car charger available on request. The space is designed for 2 but can fit up to 3.
Popular amenities for Chessington holiday rentals
Other great holiday rentals in Chessington

Self-contained annexe in leafy village near London

Beautiful two bed lodge with free parking in Epsom

Stunning 1 Bed Luxury Apartment

Lynwood Studio Apartment

Little London Escape

Private annex with parking

Merlyn , self contained annex Thames Ditton

Studio in Epsom
When is the best time to visit Chessington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $176 NZD | $181 NZD | $178 NZD | $204 NZD | $206 NZD | $221 NZD | $213 NZD | $213 NZD | $200 NZD | $216 NZD | $178 NZD | $197 NZD |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 15°C | 11°C | 8°C | 5°C |
Frequently Asked Questions
How much does it cost to stay in apartment rentals in Chessington?
Experience the best of Chessington with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chessington have free parking?
Absolutely! We offer over 20 house rentals with free parking in Chessington. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Chessington?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with a kitchen, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Chessington?
Yes! Work meets play with ease at over 10 vacation rentals in Chessington featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Chessington have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Chessington. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Chessington?
Chessington has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Where should I stay in Chessington?
Make yourself at home in Chessington by choosing from our most frequently booked neighborhoods. We have over 990 vacation rentals in Hook, over 120 vacation rentals in Malden Rushett, and over 2,970 vacation rentals in Chessington.
Are there pet-friendly vacation rentals in Chessington?
Four-legged friends are welcome in Chessington. Choose from more than 10 vacation rentals for guests traveling with pets.
Quick stats about holiday rentals in Chessington

Total holiday rentals
Explore 50 holiday rentals in Chessington

Nightly prices starting at
Chessington holiday rentals start at $52 NZD per night before taxes and fees

Verified guest reviews
Over 1,310 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
50 of Chessington holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chessington rentals

4.8 Average rating
Chessington stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Tower Bridge
- Big Ben
- Paddington
- British Museum
- Natural History Museum
- Covent Garden
- London Bridge
- Marble Arch
- Tottenham Court Road
- Buckingham Palace
- Kings Cross
- Hampstead Heath
- The O2
- St Pancras International
- Piccadilly Theatre
- Trafalgar Square
- Battersea Power Station (disused)
- Emirates Stadium
- ExCeL London
- Royal Albert Hall
- Wembley Stadium
- Olympia Events
- Russell Square
- Borough Market




