Vacation rentals in Wainscott

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Top-rated vacation rentals in Wainscott

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Top guest favorite
A charming Victorian lodge is positioned along a quiet single track road, featuring a welcoming entrance with a white gate and green doors. Surrounding fields and trees are visible in the background under a clear blue sky.
Cottage in Wainscott
5.0 out of 5 average rating, 64 reviews

Victorian gardener's lodge set in Kent countryside

This Victorian gardener's lodge house has recently been refurbished to create an idyllic country escape. Situated just out of town, this pretty country cottage is set within one corner of the main house's walled kitchen garden. Cosy up with a book in front of the log burner, or enjoy a morning coffee in the small cottage garden at the front, with views across arable fields & woodland. Relax with a glass or two on the stone paved terrace at the back of the cottage, the best place for a sundowner.

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Superhost
Home in Kent
5.0 out of 5 average rating, 4 reviews

The Picture House | Kent

Experience luxury, comfort and entertainment at The Picture House in Kent, a stylish detached 4-bed retreat sleeping up to 6 guests. Enjoy a private cinema suite, Jacuzzi bath and an 85ft garden with a fire pit. A 15 minutes drive to St Andrews Lake, a beautiful blue lake reserve packed with exciting water and land activities. Just a short walk to Mid Kent Golf Club, and only 17 minutes by train to Central London. Perfect for families, groups and business stays, with free parking and fast Wi-Fi.

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Top guest favorite
Home in Kent
5.0 out of 5 average rating, 21 reviews

Contractors Haven - 4 bed 4 bath

Tim & Natalie welcome you to this spacious, modern 4-bedroom home in a quiet cul-de-sac in Gravesend East. Perfect for contractors, families and longer stays. All bedrooms have private bathrooms (3 en-suite plus one main bathroom), TVs & fans. Dedicated workspace and fast WiFi throughout. Driveway parking for up to 4 cars with no height restrictions, plus a large private garden. Excellent access to A2 & M25. Short walk to local shops & pub, with easy links to Gravesend Station & Bluewater.

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Guest favorite
Home in Lower Upnor
4.98 out of 5 average rating, 44 reviews

Charming Riverside Home in Historic Kent Village

Stylish 3-storey 4-bedroom holiday home in the historic riverside village of Lower Upnor, Kent. Features include a spacious kitchen, cosy lounge with Smart TV, Wi-Fi, 1 main bathroom, en-suite to master, and downstairs WC. Enjoy the terraced garden with outdoor seating. Walk to Upnor Castle, river paths and traditional pubs. Easy access to Rochester, Strood (London trains), A2/M2 and family attractions. Free parking for 2 cars. Ideal for families, groups, professionals or short breaks.

LocationFamilyRiver

Top guest favorite
A bright living area is present, featuring two dark leather sofas positioned on a plush area rug. A small wooden table holds a vase of flowers. Natural light enters through a skylight, complementing a mounted television and decorative elements on the mantel.
Apartment in Rochester
4.99 out of 5 average rating, 72 reviews

Castle Garden View - Central Rochester High Street

Castle Garden View is a 2 bedroom flat situated in a prime location within the bustling heart of Rochester, close to both the Castle and Cathedral. In addition to the many historical landmarks of the local area, visitors can enjoy the vibrant bars and restaurants nearby, providing plenty of dining and entertainment options right on the doorstep. The flat is within easy walking distance of Rochester and Strood railway stations and so ideal for visitors arriving by public transport.

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Top guest favorite
Guesthouse in Medway
4.98 out of 5 average rating, 42 reviews

The Back Garden Annex – Welcoming and Witty

Welcome to Your Cozy Garden Annex in Twydall! Are you visiting family nearby or setting out to explore Kent, the Garden of England? Our charming self-contained garden annex offers a warm, homely space where you can relax, recharge, and feel right at home. Perfectly located in Twydall, just a five-minute drive from Rainham, Kent train station, you’ll have direct links to central London and Kent’s iconic seaside towns — from Whitstable’s oysters to Margate’s sandy shores.

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Guest favorite
The modern two-story apartment features a sleek design with large floor-to-ceiling windows. A private patio area is visible, surrounded by landscaped greenery. The exterior showcases a combination of white and red brick, with a sloped driveway leading up to the entrance.
Apartment in Higham
4.79 out of 5 average rating, 247 reviews

Mulberry Rise Apartment

Brand new spacious apartment, decorated in a modern style with floor to ceiling windows and bifold doors. The property is secure with plenty of parking, and a private patio area. Located opposite Gads Hill School and the Sir John Falstaff pub, the area is steeped with History and Charles Dickens culture. Surrounded by fields and woods for leisurely walks and conveniently located near pubs and local shops. Whilst also near the A2 and local public transport connections.

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Guest favorite
Home in Medway
4.93 out of 5 average rating, 114 reviews

Grade II 3-bed cottage• Free parking • Sonos & 5.1

Enjoy a stylish experience at this centrally-located cottage in the heart of Rochester. The Grade 2 listed cottage was built in the 1750s but has all the comforts of high end residential living. With SONOS speakers throughout, Sky TV and 5.1 Surround sound in the lounge you have the perfect retreat if you want to relax. Town is a two minute walk if you want a drink, or make your own at the cocktail bar. The lit terrace makes the perfect place to read , eat or party.

FamilyLocationSleep quality

Top guest favorite
A charming two-story building features a classic white-clapboard façade with a large window on the upper level. The entryway is framed by a beige curtain, while greenery is visible in front of the structure. Adjacent buildings showcase brick and painted exteriors.
Cottage in Rochester
4.95 out of 5 average rating, 327 reviews

The Old Tuck Shop (entire cottage - 1 double bed)

Ideally located for exploration of the historic Medway Towns and surrounding areas of Kent,The Old Tuck Shop is the perfect place for a relaxing getaway. The accommodation can sleep up to 3 guests, but this listing is only for two guests sharing the double room. If the second single bedroom is required please contact your host before booking or see the other listing. There is a full bathroom upstairs and an additional loo and cloakroom downstairs.

LocationFamilyLayout

Top guest favorite
A dining area features a round table with wicker placemats, surrounded by black chairs. A potted plant adds a touch of greenery. Large windows offer views of the marina, showcasing boats and water reflections under a soft sky.
Apartment in St. Mary's Island
5.0 out of 5 average rating, 96 reviews

Stunning 2 Bed Chatham Docks Apartment

This stunning 2 bed apartment is the perfect place to relax and unwind situated on the marina. Come and explore the sights and local attractions of historical town of Chatham. Surrounded by restaurants, shops, bars and a multiplex cinema. Also has excellent connections to London with 2 stations being within a 10 minute drive and only taking 40 minutes to get into London via high speed making it the perfect stay for tourists and business stays.

LocationFamilyIndoor spaces

Top guest favorite
A light-filled hallway with warm wood flooring is lined with elegant wall paneling. A potted plant sits in a gold planter, adding a touch of greenery. Soft pink walls create a welcoming atmosphere, with an inviting peek of a bedroom visible through the archway.
Apartment in Rochester
4.95 out of 5 average rating, 41 reviews

The Corner by the Castle

The Corner by the Castle is our characterful first floor Victorian apartment in the heart of Rochester High Street. Sleeping 4 with two comfy double beds, a great kitchen (where you can catch a glimpse of the castle gardens from the window) it’s perfect for relaxing or exploring. Surrounded by shops, restaurants, and historic sites like Rochester Cathedral and Castle, it’s the ideal base to enjoy everything this charming City has to offer.

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Top guest favorite
A charming barn conversion is depicted amidst a grassy landscape, with a gravel driveway leading to its entrance. The structure features black wooden siding and a metal roof, surrounded by rows of pear orchards and open farmland under a partly cloudy sky.
Farm stay in Medway
4.94 out of 5 average rating, 216 reviews

Unique barn conversion with beautiful marsh views

This recently converted barn is situated on the edge of the North Kent Marshes, with stunning views of the birds and wildlife on the marshes and surrounded by pear orchards to the rear. You’ll enjoy complete privacy, with no surrounding properties and a real sense of peace and tranquillity. The property is located in the middle of a working farm, with our sheep grazing the marshes and a variety of fruit grown in the orchards.

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