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House vacation rentals in Chessington

Find and book unique houses on Airbnb

Top-rated house rentals in Chessington

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

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Superhost
A living area features a dark sofa arranged with patterned cushions. An art piece depicting the sea hangs on the wall. A coffee table is centered on polished wooden flooring, complementing the light-colored walls and large windows dressed with shutters that allow natural light to fill the space.
Home in Surrey
4.96 out of 5 average rating, 70 reviews

High Street Apartment ESHER

Newly converted town centre apartment in fantastic order throughout, offers bright, generous-sized living space. One generous sized double bedroom, ultra modern shower room, fully fitted open plan kitchen (including dishwasher) /reception room. Unlimited high speed internet connectivity. Free, designated parking is available in 100 m. Esher High Street has an excellent range of restaurants including Waitrose, Cote, Giggling Squid, The Good Earth an Everyman Cinema along with coffee shops, pubs.

Top guest favorite
The outdoor seating area features a rectangular table with a decorative flower arrangement, arranged on a light-colored tiled surface. In the background, large glass doors open to a stylish interior, revealing a modern kitchen and comfortable sofa.
Home in Greater London
4.93 out of 5 average rating, 116 reviews

The Nook

Kick back and relax in this calm, stylish space. This ground floor one bed apartment is perfect for romantic getaway with your partner, or if you are in town for work and you are looking for a home away from home. If you have a little one you want to bring with you. Victoria station is a 20 minute train away, as well as being 15 minutes away from Wimbledon and Croydon by tram. All house trained dogs of all sizes welcome. EV charging points are NOT on premise. They are on street charging points.

Superhost
A comfortable living area features a light-colored sofa and an elegant coffee table with remote controls placed atop. A flat-screen television is mounted above a decorative fireplace, with natural light illuminating the space through two windows on either side.
Home in Surrey
4.58 out of 5 average rating, 225 reviews

Detached 6 bedroom family house with Sky TV

Detached art deco house is short walk to the town centre with 30 min train links to London (Waterloo, Victoria Lon. Bridge) and close to Epsom downs and race course! All bedrooms benefit from 2 super King and 4 double beds plus high quality beds & bedding, one double sofa bed and large sofas. Family bathroom, separate shower room & WC downstairs. One bedroom is located downstairs next to the front door for easy access for guests who wish not to go upstairs. Very well equipped and clean home.

Top guest favorite
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, 325 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 favorite
The exterior view of the property showcases a black wooden structure with prominent gabled roofs and dormer windows. A warm, inviting entryway is framed by greenery, and a wooden gate is visible, providing access to a secluded area.
Home in Burpham
4.99 out of 5 average rating, 213 reviews

Ty Bach

A cosy, clean, warm and light annexe with its own walled garden. Situated on a beautiful private road a short walk from the historic cobbled streets of Guildford town centre with its numerous boutique shops and quality independent restaurants. Ty Bach is on the edge of the beautiful Surrey Hills (a designated Area of Outstanding Natural Beauty) and the Rivey Wey. It is the perfect destination for walkers, mountain bikers and lovers of the outdoors. Dog walking and country pub heaven!

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, 129 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 a spacious two-story house is captured, featuring a blend of textured cream and brick siding. A neatly landscaped front garden includes vibrant greenery. A driveway accommodates a parked vehicle, and a secure entrance with a decorative door is visible.
Home in Surrey
4.92 out of 5 average rating, 118 reviews

Cheerful 5 bedroom house with off street parking

Bring the whole family to this great place with lots of room for fun. The house is very spacious with a good sized garden. Four double bedrooms and one single bedroom. Master suite with ensuite bathroom. Main bathroom and also shower room downstairs. Plenty of kitchen area with bar seating and also washing machine in separate annexe area. Excellent transport facilities nearby with both buses and trains. Very close to The Epsom Downs Racecourse. Excellent walking area.

Top guest favorite
A light-filled living area is furnished with a plush sofa and decorative pillows. A stylish coffee table sits centrally on a patterned rug. Lush plants add a touch of greenery, while a large television rests against a sleek media console, enhancing the inviting ambiance.
Home in Surrey
4.93 out of 5 average rating, 154 reviews

Virginia Water Family Getaway

Escape to Lambly Hill, a stylish 4-bedroom home in exclusive Virginia Water, Surrey. Perfect for families and business travellers, this renovated, tranquil property offers modern luxury and a lovely garden. Located just a short walk from the train station, it provides easy access to nearby attractions such as Windsor Great Park and Wentworth Golf Club. A comfortable base for exploring the area and perfect as a base if traveling into London.

Guest favorite
Home in Surrey
5 out of 5 average rating, 6 reviews

Modern 1-Bed Self-Catering Home, Zone 6 London

Enjoy a stylish experience at this centrally-located home. This is a modern and tastefully designed self contained home, comes with a double bedroom with en-suite bathroom, fully equipped kitchen, utility room, garden and living-room with own driveway for free parking. 2 mins walk to West Ewell station from the property and it is only 35mins by train to London Waterloo It is I’deal for tourists, friends, business travellers or contractors

Top guest favorite
A modern living area features a dark grey sofa adorned with light-colored cushions. The open kitchen showcases sleek cabinetry and contemporary appliances, with wood flooring creating a warm atmosphere. Large windows allow natural light to flood the space, highlighting the stylish decor.
Home in Greater London
5 out of 5 average rating, 19 reviews

3 Bed | 5 Beds l Sleeps 6 | Garden l Free Parking

𝗦𝗣𝗘𝗖𝗜𝗔𝗟 𝗥𝗔𝗧𝗘𝗦 – Weekly & Monthly Discounts (Direct Bookings – see photo for details). Stylish 3-Bed Home with private garden, free parking, ideal for families, contractors, relocations or hospital staff. Minutes from Croydon City Centre with fast links to London Victoria & Gatwick via East Croydon Station (under 20 mins). Close to Colonnades (0.5m), Purley Way (1m), Croydon Univ. Hospital (2.2m) & historic Croydon Airport.

Top guest favorite
The entrance of a charming cottage is highlighted, featuring a dark blue door framed by white trim. Flower pots with vibrant blooms line the path, while multiple windows allow natural light to illuminate the red brick facade. A lantern-style light fixture adds a quaint touch.
Home in Halstead
4.98 out of 5 average rating, 126 reviews

The Coach House, Halstead Hall

The Coach House, Halstead Hall is a cosy, detached cottage within the grounds of the Grade II listed residence of the esteemed author Edith Nesbitt. Located in the peaceful village of Halstead, this idyllic retreat offers tranquility while being conveniently just a 20-minute train journey from London, accessible via a short taxi or bus ride to the local train station.

Guest favorite
A covered outdoor space features a circular table surrounded by comfortable seating. In the background, a hot tub is visible, with landscaped greenery enhancing the atmosphere. Soft lighting suggests a relaxing evening setting.
Home in Ewell
4.89 out of 5 average rating, 96 reviews

Orquidea Relaxation home with hot tub

Come and enjoy this peaceful time to disconnect and live a few days of relaxation. This beautiful place is newly renovated and equipped with all the amenities you need to have the best stay, with the hot tub available for you to use at all time all year round.

Popular amenities for Chessington house rentals

Quick stats about house rentals in Chessington

  • Total vacation rentals

    Explore 20 vacation rentals in Chessington

  • Nightly prices starting at

    Chessington vacation rentals start at G$8,366 GYD per night before taxes and fees

  • Verified guest reviews

    Over 310 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 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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