Cottage holiday rentals in Southend-on-Sea

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Top-rated cottage rentals in Southend-on-Sea

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Top guest favourite
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 out of 5 average rating, 39 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.

Superhost
A charming brick cottage is adorned with blooming wisteria, cascading over the windows. The well-maintained exterior features white window frames, enhancing the rustic aesthetic. Lush greenery surrounds the entrance, creating an inviting atmosphere for guests.
Cottage in Cobham
4.84 out of 5 average rating, 459 reviews

Countryside Escape in Beautiful Cosy Cottage

Wisteria Cottage is a beautiful four bedroom, listed building, set in an idyllic historic village. Perfect setting for family holiday or for people who enjoy the countryside and glorious walks. Bluewater is close by. Wisteria cottage is great for those wanting a getaway that offers nearby vibrant city as well as beautiful countryside. We have recently modernised the cottage, it’s a brilliant space! We have put a climbing frame in the garden for hours of fun for the little ones. Relax and enjoy.

Guest favourite
The exterior of a charming period cottage is visible, featuring a sloped, tiled roof and whitewashed walls. Lush greenery surrounds the entrance, with blooming flowers adding color. A gravel pathway leads to the door, flanked by planter boxes, creating a welcoming approach.
Cottage in West Mersea
4.93 out of 5 average rating, 189 reviews

Beautiful Period Fisherman's Cottage

Anchor cottage, an Historic Home and now with EV charger, is a delightful period, cottage situated in the heart of The Anchorage, once known as Mersea City on Mersea Island. It has three bedrooms, a large double, a twin room and a downstairs single bedroom. The bathroom is on the ground floor and large sitting/dining room with a gas heater and provides plenty of space for five people indoors and there is a private, wrap around garden with BBQ area that enjoys the sun at most times of the day.

Superhost
The exterior of a charming Victorian cottage is displayed, featuring a blend of red brick and painted clapboard. Two dormer windows with green roofs are visible. A well-maintained garden with flowers adorns the front, complemented by a small pathway leading to the main entrance.
Cottage in Tollesbury
4.9 out of 5 average rating, 176 reviews

2 Bed Coastal Cottage. Paddleboard. Dogs welcome.

This spacious Victorian cottage is a great base to explore the coast , walk, birdwatch or paddleboard. Situated in the traditional fishing village of Tollesbury the cottage has a lovely dining area, fully stocked kitchen, two large bedrooms and garden. We’re a 5 minute walk from the water and access to miles of coastal seawall walks and nature reserves looking over the river Blackwater. Tollesbury is a popular place in summer with a saltwater swimming lido and many water based activities.

Top guest favourite
A comfortable outdoor seating area is surrounded by lush greenery, displaying a modern sofa set beneath the sun. Light reflects off the water in the background, where moored boats can be seen, creating a serene setting by the shoreline.
Cottage in West Mersea
4.95 out of 5 average rating, 286 reviews

Cottage on the beach

With its own beachside garden and breathtaking uninterrupted views of the wildest of Essex creeks and marshes, the cottage is only to be reached on foot atop a sea wall. The perfect retreat from the hustle and bustle of everyday life. The last in a row of westerly facing cottages, perfect to watch the evening sun go down . From the front garden or even laying in bed, watch the tide slip in and out, the fishing boats come and go and live, for a while, in a world moving at a slower pace.

Guest favourite
The living area features exposed wooden beams, complimented by a cozy two-seater sofa and a reading chair. A round coffee table sits at the center, with natural light illuminating the space through multiple windows. A flat-screen TV is mounted on the brick wall.
Cottage in Allhallows
4.96 out of 5 average rating, 23 reviews

Charming cottage with hot tub & private garden

Nestled in the heart of the serene village of St. Mary Hoo, our cottage offers a unique escape into the tranquility of the Kent countryside. This retreat offers a sanctuary where guests can truly relax and rejuvenate, with the help of a private garden and hot tub. Whether you’re a family on holiday, a couple in search of a peaceful countryside retreat, or a professional needing a quiet and comfortable place to unwind after a long day’s work – our cottage provides the ideal sanctuary.

Superhost
A cozy living area features a comfortable beige sofa set adorned with red and white striped cushions. A wooden coffee table sits centered, topped with a small plant. A charming stone fireplace with a wood-burning stove is positioned against a brick wall, surrounded by soft lighting.
Cottage in Essex
4.79 out of 5 average rating, 134 reviews

3 bed cottage, on private tranquil lane.

Self check-in assured at this charming former railway cottage situated on a private lane. We have a reputation for complete cleanliness and we are extremely vigilant on behalf of our guests. Back to the fun stuff, this cosy cottage has many original features. Step outside and there is a private south-facing secure garden with lovely new large patio, and a gorgeous suntrap for most of the day. Free parking. Doggies and cats are most welcome. We are a 10 min walk to the town centre.

Top guest favourite
A row of colorful beach huts lines a sandy shoreline. Each hut features a pitched roof and a front porch with steps leading down to the beach. The clear blue sky above enhances the vibrant hues of the huts, creating a cheerful seaside atmosphere.
Cottage in West Mersea
4.92 out of 5 average rating, 254 reviews

Woodbine Cottage

Whether you’re get up and go types or would rather relax than rush, you’ll find Mersea has something to suit everyone’s taste and pace. Just take a short stroll from the cottage and you’ll discover a delightful esplanade and beach, two rather nice pubs, cafe’s, a yacht club and the famous seafood eateries. You’ll hear the bells ringing out from the sailing boats and see kids enthusiastically crabbing from the jetty. We fell head over heels in love with Mersea and hope you will too.

Top guest favourite
A panoramic view of the Thames Estuary is captured through large skylights. Fishing boats dot the expansive water, with a backdrop of distant land under a clear sky. The foreground reveals rustic buildings by the shore, adding to the coastal setting.
Cottage in Southend-on-Sea
4.97 out of 5 average rating, 38 reviews

Stunning 2 bedroom fisherman’s cottage, Old Leigh.

Completely renovated 2 bedroomed Fisherman’s cottage in the heart of Leigh on Seas’ old town with fabulous views to the rear over the Thames Estuary. The cottage is centrally located within meters of Leigh beach and the waterside bars and restaurants of the old town. Leigh-on-Sea train station is a 10 minute walk past the historic cockle sheds and the popular Broadway is with a short stroll with its many independent shops and boutiques and more bars and restaurants.

Guest favourite
The exterior of the cottage showcases a blend of dark wood and brick, with a welcoming front door framed by large windows. A small garden area is visible, providing a natural touch. A dog is seen in the foreground, adding to the homey atmosphere.
Cottage in West Mersea
4.91 out of 5 average rating, 158 reviews

Comfy, quiet beach cottage for walking & seafood

'The Cabin' is a comfortable, bright, two bedroom cottage on Mersea Island, a few steps from the sea on a much sought after quiet lane. There are two double bedrooms, one with a Super King bed the other with a King size bed and a bunk bed. There are great walks and bike rides either along the sea wall or on the beach, and some fantastic seafood eateries. Mersea Island is off the coast of Essex, 9 miles southeast of Colchester, just one hour from London.

Top guest favourite
A patio area features a round table set for two, accompanied by metal chairs. A tray holds glasses and a bottle, with a view of the estuary visible in the background. The surrounding greenery complements the outdoor ambience.
Cottage in Southend-on-Sea
4.91 out of 5 average rating, 87 reviews

Bright modernised cottage with Estuary views

A fisherman's cottage set in a tucked away corner of Old Leigh with its many pubs and restaurants, just a short walk up the hill to the Broadway with its bustle of shops and coffee bars. Double bedroom, shower room, fully equipped kitchen with oven, hob, Smeg fridge, dishwasher and washing machine. Comfortable lounge setee and 42" smart TV. A large patio with table and benches, steps leading to lawn. Estuary view from shower room, kitchen and sitting room.

Top guest favourite
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, 313 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.

Popular amenities for cottage rentals in Southend-on-Sea

Quick stats about cottage rentals in Southend-on-Sea

  • Nightly prices starting at

    Southend-on-Sea holiday rentals start at $180 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,010 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Southend-on-Sea rentals

  • 4.9 Average rating

    Southend-on-Sea stays are highly rated by guests – averaging 4.9 out of 5!

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