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Vacation rentals in Chessington

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Top-rated vacation rentals in Chessington

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A modern living area is highlighted by a spacious sectional sofa with a soft throw, complemented by a glass table and white chairs in the dining nook. A large mirror reflects light from the window, while a wall-mounted television provides entertainment options.
Apartment in Surrey
4.97 out of 5 average rating, 72 reviews

Modern flat in central location

Enjoy unparalleled comfort in our top-floor 2BR flat in central Epsom, just 5 min from the station & high street. Sleep soundly in a king, double, or single bed, and relax in a stylish space featuring a 55" Smart TV, espresso machine, and more. Benefit from secure parking, a peaceful setting, and proximity to town. Modern aesthetics meet practicality in our recently refurbished, secure building. Ideal for exploring Surrey or soaking in the quiet. Your serene, chic getaway in the heart of it all!

Top guest favorite
The living area features high wooden beams and a large window allowing natural light. A comfortable sofa is placed alongside classic armchairs. A kitchen area with cabinetry is visible, complemented by a decorative lamp and houseplants. Soft textures enhance the cozy environment.
Cottage in Chobham
4.99 out of 5 average rating, 113 reviews

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.

Guest favorite
A light-filled living area features a comfortable blue sofa and a pink armchair. A coffee table sits between them, while a large window with a balcony provides a view of the vibrant trees outside. A Smart TV is positioned on a media console opposite the seating.
Condo in Royal Kingston upon Thames
4.96 out of 5 average rating, 25 reviews

Stunning 1 Bed Luxury Apartment

A stunning new development of luxury apartments in Surbiton - less than 10 min from Wimbledon by train!. The apartment is completed to an exceptional specification, with an Italian finish bathroom, a fully equipped contemporary kitchen, unlimited high-speed Wi-Fi, and a Smart TV. It also benefits from a nice balcony facing south and lovely The Wood park and bird sanctuary view - a truly peaceful place to rest after a busy day. Lockwood House is an ideal option for leisure and business guests.

Top guest favorite
The room features a spacious double Queen bed adorned with clean white linens. A bedside table with a lamp complements the bed. A small TV is positioned on a stand across from the bed, while natural light enters through a nearby window.
Guest suite in Claygate
4.94 out of 5 average rating, 176 reviews

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.

Top guest favorite
Rowers glide across the still waters beneath an arched bridge adorned with decorative lamps. Moored boats with wooden tables are positioned in the foreground, reflecting the vibrant autumn foliage from trees lining the riverbank.
Apartment in Royal Kingston upon Thames
5 out of 5 average rating, 18 reviews

Sunny Riverside Victorian Flat

Charming Victorian conversion set on idyllic River road Location: Picturesque, tree-lined street just 2 minutes from the Thames and 20 mins to Central London. Bright, sun-filled rooms, thoughtfully decorated with warmth—this is my home, not just a rental. Fully equipped kitchen and spacious bedroom. Enjoy scenic walks or bike rides to nearby attractions – Hampton Court Palace, Richmond Park, and Kingston’s lively market . Quiet street with cafés, shops, and all essentials nearby.

Top guest favorite
The open plan living area features gabled ceilings and stylish furnishings. A comfortable sofa sits across from a galley kitchen with modern cabinetry. French windows open to a private patio garden, while natural light enters through sheer curtains, creating a bright and inviting atmosphere.
Home in Molesey
5 out of 5 average rating, 128 reviews

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.

Guest favorite
The exterior of the studio features a smooth patio area framed by potted plants and a wooden bench. Large windows line the front, allowing natural light to enter. The presence of greenery enhances the serene ambiance, set against a clear blue sky.
Guesthouse in Ewell
4.95 out of 5 average rating, 59 reviews

Studio in Epsom

This quiet studio is a 15 minute walk from Ewell West train station for a 35 minute direct train to Waterloo. The studio has; - fully functioning kitchen (combination microwave, induction hob & a milk frother (a necessity in my world)) with dining table, - relaxing space to watch TV - dedicated work space with great internet access, - cosy yet firm double bed, all feathered pillows and duvet - skylit shower bathroom, - free parking, - washing machine available (on request)

Top guest favorite
A modern living area features a plush gray sectional sofa adorned with colorful pillows. A patterned area rug adds warmth to the space, while a wall mirror reflects light. Adjacent, a compact dining area is seen, with a small table and chairs, leading into an open kitchen.
Guesthouse in Surrey
4.93 out of 5 average rating, 156 reviews

Private luxury apartment with free Secure parking

Outbuilding with front free parking (only 1 car per booking). Peaceful surroundings with west facing sun (longer days) and wildlife. Close amenities with 24 hour gas station and close shops near by, 7 mins to Epsom town and 6 mins to Chessington world of adventures (by car) and 30 mins trains straight to Waterloo. Very secure apartment as there is CCTV outside in the main house. You will truly enjoy this quiet luxury apartment. *Discount will be offered to returning guests*

Top guest favorite
A spacious loft room features a comfortable double bed with soft linens and neatly rolled towels. A cozy seating area includes two chairs and a small dining table. Natural light streams in from a skylight and window adorned with patterned curtains, contributing to a bright atmosphere.
Guesthouse in Surrey
4.97 out of 5 average rating, 315 reviews

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.

Top guest favorite
A bright lounge area features a comfortable sofa with plaid cushions, alongside a dining table and chairs. Large skylights and glass doors illuminate the space, opening to a patio garden filled with greenery. Two framed artworks enhance the inviting ambiance.
Guesthouse in Surrey
5 out of 5 average rating, 274 reviews

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.

Guest favorite
A living room features a spacious grey sectional sofa adorned with a yellow throw pillow. A round mirror is mounted above a wooden fireplace, while a small side table with a lamp and decorative items is positioned nearby. A doorway leads to an adjoining area.
Home in Royal Kingston upon Thames
4.89 out of 5 average rating, 9 reviews

Cozy Cottage-House

Make some memories at this unique and family-friendly house. Just a 5 minute drive to Chessington World of Adventures & a 20 minute drive to Wimbledon Tennis. A cosy but spacious, family friendly house with a 5 minute walk to Chessington North train station, that has direct links to Wimbledon and London Waterloo where it will take you just 35 minutes to be in Central London. Sit back and relax in the 100 foot garden, have a drink on the patio. Free parking for 2 ca

Guest favorite
A couple relaxes in a bubbling outdoor hot tub, holding glasses, with a scenic view of lush green fields and trees in the background. A champagne bottle sits in an ice bucket beside them, enhancing the tranquil atmosphere.
Shepherd’s hut in Royal Kingston upon Thames
4.98 out of 5 average rating, 344 reviews

The Ultimate Couples Retreat | 30 Mins from London

This countryside retreat is the perfect romantic escape, just a 35 minute taxi/train ride minutes from London. Unwind in your private luxury hot tub, sip on a complimentary bottle Champagne under the stars, and wake up to breathtaking views of rolling fields and wildlife. Our handcrafted shepherd’s hut blends rustic charm with modern comfort, offering a king-sized stargazing bed, a cozy fire-lit deck, and a luxury bathroom, all set in a peaceful meadow.

Popular amenities for Chessington vacation rentals

When is the best time to visit Chessington?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$21,119 GYDG$21,747 GYDG$21,329 GYDG$24,465 GYDG$24,674 GYDG$26,556 GYDG$25,511 GYDG$25,511 GYDG$24,047 GYDG$24,256 GYDG$23,420 GYDG$24,465 GYD
Avg. temp5°C5°C7°C9°C12°C15°C17°C17°C15°C11°C8°C5°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 vacation rentals in Chessington

  • Total vacation rentals

    Explore 50 vacation rentals in Chessington

  • Nightly prices starting at

    Chessington vacation rentals start at G$6,273 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,310 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Chessington vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chessington rentals

  • 4.8 Average rating

    Chessington stays are highly rated by guests—averaging 4.8 out of 5!

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