Cottage holiday rentals in Southend-on-Sea

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Top-rated cottage rentals in Southend-on-Sea

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

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Top guest favourite
The exterior of a charming studio cottage is shown surrounded by lush greenery. A flowering wisteria drapes over one side, complementing the soft yellow walls. A stylish hanging chair is positioned on the lawn, providing a comfortable outdoor seating option.
Cottage
4.96 out of 5 average rating, 247 reviews

Charming Cottage & private parking, heart of Kent.

A Kentish gem - The Garden Room is an immaculately presented little cottage nestled in the beautiful hamlet of Harvel with thatched houses, Village Greens & the best Farm Café around. We offer a full range of in house Wellness Treatments. There is walking, stables, National Trusts, Silverhand Vineyard & Brands Hatch all on our doorstep. Good transport links; railway stations at Meopham, Borough Green & Ebbsfleet providing services DIRECT from London in UNDER 45 minutes. M25/M20 are close by.

Top 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
4.94 out of 5 average rating, 211 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.

Top guest favourite
Cottage
4.97 out of 5 average rating, 202 reviews

Double fronted Period Cottage by Whitstable beach

Think Pig Hotel meets coastal hideaway! Our beautiful double fronted Victorian Cottage is a stone’s throw from the beach and restaurants in a peaceful street. Art on the walls, antiques in every room and plenty of lamps, candles, create a unique atmosphere. *Comfy beds for a good night’s sleep. *Full kitchen with a range cooker *Two Wood burning stoves *Upstairs bathroom *Private Courtyard with Weber BBQ *Free on street parking *Dog Friendly! *Baby and child friendly (cot & high chair)

Top guest favourite
The charming exterior of the cottage features dark wooden siding and a welcoming door. A gravel pathway leads to the entrance, flanked by colorful flower beds. A rustic bench is positioned near the door, offering a pleasant spot to relax among the surrounding greenery.
Cottage
4.99 out of 5 average rating, 450 reviews

Twitchers Cottage Oare - Nature on your doorstep

Twitchers Cottage at Broomfield Barn is a beautifully presented converted in 2020, one bedroom cottage. Located on the edge of Oare marshes that is an important wetland reserve with a range of bird species. This area is popular with bird watches, walkers, wildlife photographers and cyclists or anyone who wants a relaxing break away surrounded by open countryside. There is plenty to do throughout the year wether you want coast, town or countryside it’s all in easy reach for your enjoyment.

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
4.95 out of 5 average rating, 321 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
A charming cottage exterior is framed by lush greenery and mature trees. The building features a traditional wooden door and a large window, allowing natural light to fill the interior. Gravel pathways lead to the entrance, enhancing the rustic appeal of the setting.
Cottage
4.86 out of 5 average rating, 204 reviews

Cottage in the Wood, Detling

'Cottage in the Wood' contains two double bedrooms one with en-suite bath/shower and one with shower room along with a sheltered hot tub taking advantage of the rolling Kent countryside with extensive views over the local Vineyards and North Downs beyond. The small and picturesque village of Detling is found on the slope of the North Downs, just northeast of Maidstone, and on the Pilgrims' Way - ideal if you're looking for a break only a short distance away from London.​

Guest favourite
A bright living area features large windows offering views of the coastline. A comfortable violet sofa and a matching armchair are arranged around a light rug. A dining table is paired with white chairs, and a small kitchen area is seen in the background.
Cottage
4.91 out of 5 average rating, 139 reviews

Whitstable Beach Cottage Seasalter Whitstable

If you're looking for a Whitstable holiday cottage, then our beach house at Seasalter may be perfect for you. One of just a handful of beach front properties in Whitstable bay, its captivating sea views make it a great place to stay summer or winter. Living literally right on the beach is something quite special, so if your passion is fishing, bird watching or sailing, if you just want to relax, or if you need a base to explore Kent from, you'll love our beach cottage.

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
4.95 out of 5 average rating, 325 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.

Guest favourite
A charming cottage façade features a mix of red brick and white siding. The entrance is accented with a pink door, surrounded by greenery and flowering plants. Windows are adorned with white frames, allowing natural light to enhance the inviting exterior.
Cottage
4.94 out of 5 average rating, 144 reviews

2 bedroom Georgian cottage on Island Wall

A beautiful 2 bedroom cottage in the most wonderful location - steps away from the beach and a few minutes walk to the centre of Whitstable. This fisherman’s cottage dates back to 1810, is full of period charm, and sympathetically decorated with antique, comfortable furniture. The cottage has a mature garden with side access, and is set down several steps meaning it feels nice and private. The cottage has steep stairs and some low ceilings.

Top guest favourite
A modern kitchen features sleek cabinetry and a spacious dining table surrounded by several chairs. Essential appliances, including a stove and kettle, are present. Natural light enters through a window, illuminating the countertops adorned with flowers and kitchen items.
Cottage
4.96 out of 5 average rating, 323 reviews

Cosy 3 bedroom cottage in the heart of Kent

Shillinghurst Cottage is the perfect getaway for a relaxing break for friends, couples or a family break. It is cosy, comfortable yet modern and comes with everything you would expect to make it the ideal home away from home. Set in the heart of the beautiful village of Borden, it will suit individuals who like country walks, relaxing in a peaceful surrounding or exploring the many towns and cities nearby.

Top guest favourite
The bedroom features a plush kingsize bed with soft linens and an inviting assortment of pillows. Warm gray paneling surrounds the bed, complemented by stylish bedside tables with lamps. Natural light enters through a skylight, adding brightness to the cozy space.
Cottage
5 out of 5 average rating, 279 reviews

Exquisite Cottage in Beautiful Kent Countryside

This delightful cottage has been lovingly refurbished and offers a luxurious, yet cosy and comfortable space for the perfect weekend getaway. Located in a designated Area of Outstanding Natural Beauty, we are situated in the heart of our pretty village surrounded by miles of beautiful Kent countryside. A beautiful spot to indulge in countryside walks and delicious pub lunches.

Guest favourite
A spacious hot tub is surrounded by lush greenery and blooming cherry blossom trees. The inviting water is illuminated under the sun, with modern windows reflecting the outdoor scenery. A dining area can be seen in the background, further enhancing the outdoor living space.
Cottage
4.91 out of 5 average rating, 133 reviews

Daweswood Guest Suite - luxury retreat & hot tub.

Just six minutes from Canterbury city centre and ten minutes from Whitstable seafront, Daweswood Guest Suite is a flagship country retreat designed with you in mind. Does drifting to sleep whilst reading a book in the garden room hammock sound like perfection? How about relaxing in the hot tub(£48) or cooking a family feast on the BBQ(£18)?

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 £106 per night before taxes and fees

  • Verified guest reviews

    Over 1,060 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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