Vacation rentals in St. Mary's Island

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Top-rated vacation rentals in St. Mary's Island

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

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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, 65 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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Guest favorite
Apartment in Medway
4.9 out of 5 average rating, 10 reviews

Sleeps 4 | Great for Groups | Free Parking | Kent

IDG Stays & Suites is great for huge savings VS multiple hotel rooms. It is a thoughtfully designed 1BR apartment. Featuring a cosy Room with a King size bed, bright living area with a sofa bed for 2. Perfect for families & groups. Fully equipped kitchen for both short and long stays. High-speed WiFi and smart TV entertainment to unwind. Quick trips into London. Easy access to local shops, and excellent transport links. Clean and welcoming, IDG Stays & Suites is your home away from home!

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Top guest favorite
Home in Detling
4.98 out of 5 average rating, 140 reviews

Luxury 5-BedRm • Hot Tub • Games Room • Sleeps 12

Kent Downs AONB • Newly renovated 5‑bed group house (sleeps 12 + 2 infants) for friends and family get‑togethers, birthdays and wedding weekends. Flexible sleeping arrangements, private year‑round Hot Tub with views, big games room (pool/TT/foosball + 86" TV + sofa‑bed), Kamado Joe BBQ patio, superfast Wi‑Fi (1gb fibre) + Ethernet, luxury hotel‑quality linen & towels, parking for 7 cars + EV charger. Great for midweek offsites. Easy M20/M2/A249 access + Bearsted train station nearby.

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Guest favorite
Home in Lower Upnor
4.98 out of 5 average rating, 45 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.

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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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Superhost
Home in Chatham
5.0 out of 5 average rating, 5 reviews

Lush 2 Bed Home I Free Parking I Near Chatham Dock

Experience ultimate group comfort in this stylish Brompton retreat by Novasera Properties. Perfectly tailored for large families, contractors, or weekend explorers, our home uniquely sleeps 8 across two floors. Nestled in a quiet pocket of Chatham, you’re a stroll away from the Historic Dockyard and high-speed links to London. Enjoy a seamless blend of modern amenities, sleek bathrooms, and versatile sleeping options. Whether for work or play, find your perfect Medway base here.

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Guest favorite
Guesthouse in Medway
4.98 out of 5 average rating, 43 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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Superhost
Home in Medway
4.85 out of 5 average rating, 13 reviews

Gill Perfect for Contractors Parking x1 Pool Table

Planning a long-term stay? This spacious and beautifully presented 3-double bedroom end of terrace house offers the perfect home away from home. Located in a quiet neighbourhood, it’s ideal for contractors, business travellers, or families. Enjoy the generous living space including 2 receptions, perfect for relaxing after a busy workday. The private garden adds a touch of greenery and calm. Conveniently located near Gillingham Station, with direct links to Central London

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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.

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Superhost
Home in Medway
5.0 out of 5 average rating, 3 reviews

4BR Family Home| 2 Parking Spaces | River View

🏡 Modern New-Build Family Home in Rochester Enjoy a bright, comfortable new-build home in a fantastic Rochester location ✨ 🚆 Just 5 minutes from Rochester Station Moments from the River Medway 🚗 2 dedicated parking spaces Private garden 🛜Fast Wi-Fi Brand-new appliances throughout Rochester Cathedral & historic High Street within walking distance Close to Rochester Independent College Perfect for families, professionals and longer stays.

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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.

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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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Popular amenities for St. Mary's Island vacation rentals