Southend-on-Sea Cottages

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British Travel Award Winners!

We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Southend-on-Sea Cottages

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Your Southend-on-Sea, Southend-on-Sea search returned 99 cottages

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A brick garage with white doors and a reserved parking sign with plants in pots on a paved driveway at Little Haven in Kirby Cross
27
Kirby Cross, Essex, CO13
  • Sleeps4
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

Little Haven is a spacious garage conversion situated on a residential development the village of Kirby Cross, Essex. Open-plan. Wheelchair-friendly. Frinton-on-Sea 2.3 miles; Walton-on-the-Naze 2.7 miles. (Ref. 1146110)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from $559

Last booked 2 days ago
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A living room with a brown sofa a patterned rug a black TV stand and a small dining table next to an open doorway leading to a kitchen at 37 Hanbury Gardens Colchester
20
Colchester, Essex, CO4
  • Sleeps4
  • Bedrooms3
  • PetsYes

    Sykes Rating

37 Hanbury Gardens is a pet-friendly, semi-detached holiday home, with an enclosed garden, resting in the historical town of Colchester in Essex. Mersea Island 11.1 miles; Clacton on Sea 16.1 miles; London 68.8 miles. (Ref. 1163469)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $558

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A brick house with a white door and a red mailbox in a garden with a tree and wooden fence at Weir Cottage in Hollingbourne
26
Hollingbourne, Kent, ME17
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.6

    Sykes Rating

This terraced property is located in Broomfield near the village of Hollingbourne in Kent. Large garden. Woodland setting. Maidstone 5.7 miles; Rochester 13.1 miles; Canterbury 23.2 miles. (Ref. 1002756)

  • Wi-fi
  • Off-road parking

7 nights from $958

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A garden with lawn chairs a table hedges and a brick house at Little Pontus in Molash near Challock
41
Molash near Challock, Kent, CT4
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Sykes Rating

A romantic cottage sitting in Molash near Challock, Kent. Off-road parking. Woodburning stove. Smart TV. Swimming pool. Rural location. Bedroom with en-suite. Faversham 8.5 miles; Ashford 8.6 miles; Canterbury 10.8 miles. (Ref. 1070677)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Dishwasher
  • Washing machine

7 nights from $828

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An outdoor patio area with chairs a fire pit and plants at Ditsys Den in Paddock Wood Kent
14
Paddock Wood, Kent, Kent, TN12
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.5

    Sykes Rating

This wonderful ground-floor studio apartment rests on the outskirts of Paddock Wood, Kent. Pet-friendly. Off-road parking. Open-plan. Maidstone 8.7 miles; Tonbridge 9 miles; Royal Tunbridge Wells 9.9 miles. (Ref. 1080904)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Baby-friendly

7 nights from $563

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An outdoor area with two chairs and a table beside a dark green hut under trees at The Shepherds Hut at Marley in Marley near Barham Kent
12
Marley near Barham, Kent, Kent, CT4
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

Pretty shepherd's hut located on the fringes of Canterbury, near Barham in Kent. WiFi. Countryside views. Log burner. Pub 1.2 miles. Canterbury 7.4 miles; Dover 14.2 miles (Ref. 1075279)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Baby-friendly

7 nights from $509

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A wooden farmhouse with hanging flower baskets and a gravel driveway with a Bolton Farmhouse sign on a wooden post at Bolton Barn in Lenham Heath near Ashford
24
Lenham Heath near Ashford, Kent, ME17
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

A cosy, comfortable barn conversion in a rural setting near Lenham. All ground floor. Beams. Excellent location for walking and cycling. Lenham 3 miles. (Ref. 27285)

  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from $482

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A house exterior with a turquoise door and two windows next to a gravel pathway and a tree at The Garden House Cottage in Whitstable
24
Whitstable, Kent, CT5
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.5

    Sykes Rating

A charming, one-bedroom annexe perched in Whitstable, Kent. Ground-floor accommodation. Off-road parking. Close to amenities and a beach. Canterbury 7.8 miles; Margate 16.8 miles; Broadstairs 19.6 miles; Dover 30.4 miles. (Ref. 1131940)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom

7 nights from $582

Last booked yesterday
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A small light blue wooden cabin with glass doors leading to a wooden deck with plants and a table with two glasses of white wine at The Artist's Cabin By The Sea in Herne Bay
20
Herne Bay, Kent, CT6
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.6

    Sykes Rating

The Artist's Cabin By The Sea is a quirky cabin resting in the coastal town of Herne Bay, Kent. Close to a beach. Couple’s retreat. Woodburning stove. Birchington-on-Sea 8.1 miles; Canterbury 9.7 miles; Ramsgate 14 miles. (Ref. 1149042)

  • Wi-fi
  • Ground floor bedroom

7 nights from $617

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A gravel driveway leading to a small house with wooden doors and windows surrounded by trees and shrubs at The Old Stables in Headcorn
38
Headcorn, Kent, TN27
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

The Old Stables is a charming annexe, within extensive grounds boasting a lake, meadow, fields, and orchards, in the quaint village of Headcorn, Kent. Staplehurst 4.2 miles; Maidstone 9.2 miles; High Weald National Landscape 14.2 miles. (Ref. 1162125)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom

7 nights from $659

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An outdoor area with a wooden fence gravel ground plants and a white door at Westgate Cottage in Sittingbourne
35
Sittingbourne, Kent, ME9
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Sykes Rating

A ground floor annexe situated near the hamlet of Oad Street near Sittingbourne in Kent. Pet-friendly. Garden with patio area. Sittingbourne 1.7 miles; Rochester 10.2 miles; Tunbridge Wells 31.2 miles. (Ref. 960985)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from $497

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A living room with beige sofas red cushions a red carpet and a dining table with red floral placemats at Barons Mews in Herne Bay
26
Herne Bay, Kent, CT6
  • Sleeps3
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

A lovely, two-bedroom cottage resting in the heart of Herne Bay, Kent. Close to the beach and amenities. Pet-friendly. Ground-floor accommodation. Enclosed garden. Whitstable 5.5 miles; Canterbury 8.1 miles; Broadstairs 16 miles; Dover 29.1 miles. (Ref. 1126171)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom

7 nights from $909

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A patio with outdoor furniture and a chiminea next to a white house with a garage and green lawn at The Old Dairy in Herne near Herne Bay
24
Herne near Herne Bay, Kent, CT6
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.5

    Sykes Rating

A detached, single-storey Herne Bay cottage in the village of Herne, near to its larger neighbour Herne Bay. Cosy accommodation with vaulted ceiling. Walking distance to shop and pubs. (Ref. 3975)

  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from $537

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A brick house with white framed windows a wooden door and a gravel driveway next to a wooden shed at 3 Apsley Cottages in Chartham near Canterbury
13
Chartham near Canterbury, Kent, CT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Sykes Rating

Delightful terrace cottage in village of Chartham with excellent links to Canterbury. Very comfortable sitting room and glorious country views. Canterbury 3 miles. (Ref. 23423)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from $431

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A small backyard with wooden pergola posts gravel ground and a wooden bench at 493 Little Wakering Road Barling Magna near Little Wakering
13
Barling Magna near Little Wakering, Essex, SS3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.4

    Sykes Rating

A bright and airy annexe resting in Barling Magna near Little Wakering, Essex. Open-plan. Washing machine. Close to amenities. Rochford 4.1 miles; Southend-on-Sea 5.7 miles; Essex 16.7 miles. (Ref. 1105037)

  • Off-road parking
  • Ground floor bedroom
  • Washing machine

7 nights from $532

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A garden patio with a small table and chairs outside a house with open doors at The Annex in Thorrington
20
Thorrington, Essex, CO7
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

The Annex is a pleasant, single-storey cottage resting in the village of Thorrington, Essex. Ground-floor living. Off-road parking. Near pub and shop. Brightlingsea 3.1 miles; Clacton-on-Sea 7.3 miles; Colchester 8.5 miles. (Ref. 1111076)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly

7 nights from $526

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A group of vintage railway carriages on tracks near trees at The Brake Wagon at High Barn Heritage Greenstead Green near Halstead
26
Greenstead Green near Halstead, Essex, CO9
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Sykes Rating

A lovingly converted passenger train carriage resting in Greenstead Green near Halstead, Essex. Countryside views. Rural. Ground-floor living. Romantic. Original features. Braintree 5 miles; Colchester 14.9 miles. (Ref. 1117637)

  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from $553

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A brick house with multiple windows a blooming tree and garden with green lawn at Paddock View in Maidstone
41
Maidstone, Kent, ME15
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    Sykes Rating

This charming annexe rests on the owners' grounds in a peaceful location in East Farleigh near Maidstone, Kent. Designated parking. Garden. Close to amenities. Rochester 11.5 miles; Canterbury 31.1 miles (Ref. 1125491)

  • Wi-fi
  • Off-road parking
  • Washing machine
  • Baby-friendly

7 nights from $576

Last booked yesterday
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A grassy yard with two small horses near a small building surrounded by trees at Badger View in Culverstone Green near Chatham
23
Culverstone Green near Chatham, Kent, DA13
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

Delightful, detached lodge, Elevated location with wonderful views, Forest to the rear and a haven for wildlife, ideally suited to animal lovers, Perfect romantic retreat, Ideal for walking, touring and relaxing, WiFi, Sevenoaks 11.5 miles. (Ref. 946987)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from $571

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A house with white siding brown framed windows a brick driveway and garden at Oakleaves in West Mersea
22
West Mersea, Essex, CO5
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

Oakleaves, a charming, ground-floor cottage resting in West Mersea in Essex, boasting off-road parking, an open-plan layout, and a short walk to a beach. Peldon 3.7 miles; Abberton 4.6 miles; Colchester 10 miles. (Ref. 1165468)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from $649

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Map View

 

Just show me Southend-on-Sea Cottages

Visit Southend-on-Sea and discover a vibrant township that strikes the perfect balance between traditional and contemporary. For decades, this lively seaside town has been a popular weekend holiday destination for hectic Londoners, and is now considered one of the most up and coming coastal destinations in the UK- take a step down the town's extraordinary 7 mile seafront, and you'll soon discover why! Here at Sykes, we recognise a good holiday destination when we see one, and now offer wonderful self-catering accommodation to rent in Southend-on-Sea. Enjoy all the benefits of a Sykes' self-catering holiday home during your stay in this vibrant coastal town, and look forward to a holiday you'll never forget.

Attractions near your Southend-on-Sea holiday home

During a visit to Southend-on-Sea, some may wish to stay close to the town's remarkably long seafront, whilst others will want to venture further afield in search of things to see and do. However you plan on spending your holiday in Southend, you'll be well catered for and central to most attractions should you rent a Southend-on-Sea holiday cottage. Seafront attractions include a bustling pier, penny arcades and mile after mile of sandy beaches, whilst in the town, independent boutiques, mouth-watering eateries and charming pubs await.

From Southend-on-Sea Pier and the Marine Activities Centre, to Southend Planetarium and the Central Museum, there's a wealth of things to see and do in this wonderful seaside town. Rent a self-catering cottage in or near Southend-on-Sea today, and discover one of the UK's favourite coastal destinations today.

If you still haven't found what you're looking for, check out the full list of cottages in Essex or these Essex short breaks. If you're bringing your dog along, then these dog-friendly cottages in Essex might be more helpful.