Vacation rentals in St. Mary's Island

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

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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

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.

5.0 out of 5 average rating, 68 reviews
Top guest favorite
Home in Detling

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.

4.98 out of 5 average rating, 147 reviews
Top guest favorite
Cabin in Rochester West

Cosy Rural Retreat with Log Burner

The Snuggery is a converted outbuilding that has been set up for a cosy stay with a wood burning stove and lots of snuggly wraps to cuddle up in. The open plan interior, high vaulted ceilings and natural oak flooring create an interior which is fun, light and airy. Walking enthusiasts will enjoy walks from the back door straight on to the North Downs Way and there is a bench by the front door fitted with a heated element, perfect for warming up your walking boots. Photos by Chloe-Rae 

4.95 out of 5 average rating, 533 reviews
Top guest favorite
Home in Lower Upnor

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.

4.98 out of 5 average rating, 46 reviews
Top guest favorite
A balcony view is captured through bi-fold glass doors, featuring a small round table and two folding chairs. A decorative pumpkin sits at the center, with panoramic sea views of the estuary and boats in the distance, framed by a serene sunset.
Condo in Southend-on-Sea

Estuary Views Penthouse with Private Parking

A Beachfront Coastal Retreat with private driveway parking & situated in the sort after area Thorpe Bay. Boasting unspoilt Panoramic Sea Views. Central to Blue Flag Beaches, 2 mins from award winning restaurants, superb location for coastal walks, watching the seabirds & a short walk to the longest Pier in the world. Re-Designed with Bi-Folding Glass doors, bringing the Outside Inside. Intricately Designed embracing tiny details that define our property for a Luxury & cosy stay.

4.99 out of 5 average rating, 441 reviews
Superhost
Apartment in Medway

Modern 2BR Apt | Sleeps 4 | Gillingham Pier

❗ Special Discount applied❗ 🌿 Peaceful Riverside Apartment | Family Friendly Relax with the whole family in this calm, comfortable apartment by the river. 📍 Great location: • Large Asda just around the corner • Close to Medway universities • Easy access to M2 & A2 • Dockside Outlet only 3 min drive away ☕ Enjoy riverside walks, coffee shops, bars and plenty of restaurants nearby. ❄️ Includes A/C and fans for extra comfort — perfect for families, work stays or weekend breaks.

5.0 out of 5 average rating, 3 reviews
Superhost
A cozy living area features a black sectional sofa and an armchair beside a small side table. An assortment of framed artwork adorns the walls, complemented by a disco ball pendant. A coffee table with a floral arrangement sits at the center, inviting relaxation.
Apartment in Rochester West

Central Rochester flat with garden, sleeps up to 4

Cosy, 1 bedroom flat in listed building in quiet street Close to the charming historic high street and the beautiful Vines park 5-10 minutes walk from Rochester train station with fast trains to London and the Kent coast 1 double bedroom 1 double pull out sofa bed in living room Small kitchen but with all you need Spacious shower A small courtyard garden - being renovated please beware of uneven surfaces Daily paid vouchers for street parking Please note access via steep stairs

4.84 out of 5 average rating, 19 reviews
Top guest favorite
Barn in Hernhill

Your next family & friends country getaway

Feel energised when you stay in this rustic gem, with a shop, cafe, summer bar and weekly events on site you won’t be short of things to do. And don’t forget the peacocks that’ll be roaming around… don’t worry they’re not scary! With the 4 bedrooms on the ground floor, two of which have French doors out to a patio, and the open plan entertaining space upstairs you’ll have plenty of bright light flooding in and access to the large deck with stunning sea views. Great for groups!

5.0 out of 5 average rating, 20 reviews
Guest favorite
Home in Medway

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.

4.93 out of 5 average rating, 117 reviews
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 West

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.

4.95 out of 5 average rating, 328 reviews
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

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.

5.0 out of 5 average rating, 99 reviews
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 West

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.

4.94 out of 5 average rating, 47 reviews

Popular amenities for St. Mary's Island vacation rentals