Holiday rentals in Skegness

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Quick stats about holiday rentals in Skegness

  • Total holiday rentals

    Explore 510 holiday rentals in Skegness

  • Nightly prices starting at

    Skegness holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,790 verified reviews to help you choose

  • Family-friendly holiday rentals

    410 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 210 rentals that welcome pets

  • Holiday rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wifi availability

    380 of Skegness holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Skegness rentals

  • 4.6 Average rating

    Skegness stays receive an average rating of 4.6 out of 5 from guests

Top-rated holiday rentals in Skegness

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

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Top guest favourite
A stylish living area features a black television mounted on a light gray wall. Two sofas, one black and one yellow, are arranged around a circular coffee table. A patterned area rug adds color to the space, complemented by natural light from large windows with blinds.
Home in Lincolnshire
4.98 out of 5 average rating, 50 reviews

Sea Breeze House

This stylish place to stay is perfect for group trips. Situated in the heart of Skegness, this newly refurbished holiday home sleeps for 6 people with its stylish and unique interior to give you that perfect seaside experience and stay. 🛏️ 🏖️ Walking distance from some fantastic town restaurants, bars, golf courses and the beach 🍛⛳️🏖️ This holiday home will give you the perfect peaceful stay and we can assure you that you will be coming back to the seaside time and time again once visited.

Guest favourite
Cabin in Boston Lincolnshire
4.91 out of 5 average rating, 1,306 reviews

Adults Only Cabin With Log Burning Hot Tub

Lakeside Fishing Retreats offers peaceful lakeside stays in the middle of nowhere, yet perfectly placed. Just 8 miles from Boston town, 12 miles from Skegness Beach and 3 miles from the coast with award-winning RSPB marshes. We have 28 Cabins set on a 3 acre lake: - Adult Only Double Cabin with Log Burning Hot Tub (Pet friendly/Non Pet friendly Cabins) - Standard Double (Child/Pet friendly/Non Pet friendly Cabins). - Twin Cabin (Child/Pet friendly) You can also enjoy our onsite Pizza Shed & Bar!

Top guest favourite
A sandy path meanders through tall, golden grass, leading towards a clear blue sky. The scene captures the natural beauty of the coastal area, with gentle undulations in the landscape enhancing the serene atmosphere.
Cottage in Chapel Saint Leonards
5 out of 5 average rating, 51 reviews

Luxury coastal cottage with private beach access

'Miles' is a spacious bungalow with large garden and private access to the beach. The charming blue holiday home is situated on a quiet road at the north end of Chapel St Leonards. 500 metres to the south is the centre of the village with a traditional seaside resort flavour of cafes, bars, shops and arcades. For a quieter vibe, head north along the beach, via Chapel Point to vast stretches of sandy coastline, coastal country park and wonderful walking, cycling and nature spotting possibilities.

Top guest favourite
The living room features a spacious dark blue sofa, a yellow armchair, and a cozy ottoman. A large flat-screen TV is mounted on the wall, while windows provide natural light, enhancing the airy atmosphere. A potted plant adds a touch of greenery to the space.
Apartment in Skegness
5 out of 5 average rating, 26 reviews

Parkview Holiday apartments Skegness

Parkview says it in the name! This property is an ideal location, being only two minutes from the town centre and two minutes from Skegness beach. The property boasts stunning views of the park so you can unwind from all your daily excitement "with some well deserved tranquility." Parkview has a double room with king size bed,twin room and a bunkbed room . The kitchen has a beautiful equipped dining area and the lounge has a 65 inch TV, making it the perfect place for some quality family time.

Guest favourite
A well-lit bedroom features a spacious bed covered in a light grey blanket. A wall-mounted television displays a scene of a beach. A mirror is mounted on the wall, while a window with a dark blind allows for natural light.
Flat in Lincolnshire
4.86 out of 5 average rating, 29 reviews

Olivias Apartments. Flat 1

The Olivia’s apartments are situated in central Skegness next door to Weatherspoons and only a minutes walk from the town centre and the train station. The apartment comprises of 1 main bedroom with a double bed, 1 open plan kitchen/lounge with a sofa bed and 1 bathroom. The apartment is situated above the popular Olivia’s Cocktail and Wine Bar and therefore some noise can be heard in the apartment above, however free drinks vouchers are present for guests to come and savour the atmosphere.

Top guest favourite
A charming log-house is set in a wooded area, featuring a dark exterior with a sloped roof. A welcoming porch with wooden railing is visible, and a vintage lamp post adds to the ambiance. Autumn leaves cover the ground, creating a peaceful atmosphere.
Treehouse in Hagworthingham
4.93 out of 5 average rating, 102 reviews

Narnia: Magical Woodland Loghouse with Hot Bath

Step into a magical woodland hideaway. Perfect for couples, families, remote workers (dog-friendly), enjoy an outdoor hot bath, private woodland, and a mezzanine treehouse. Cozy by the fire pit, cook in the fully equipped kitchen, listen to birdsong and rustling leaves, and lose yourself in a place where time slows and memories linger. Romance, adventure, and mindful work meet nature’s tranquility in this fairytale escape in Lincolnshire Wolds and only 20 minutes from golden sandy beaches.

Guest favourite
A comfortable lounge area is presented with two light-colored armchairs facing a flat-screen television. A faux fireplace adds warmth to the space, complemented by a textured area rug. Large windows allow natural light to illuminate the room, framed by flowing curtains.
Apartment in Lincolnshire
4.96 out of 5 average rating, 26 reviews

Skegness Home 4 people, 2 bedroom, walk to the sea

This delightful 2 bedroom maisonette on the FIRST FLOOR which is close to the bus/train stations, main high street, Hildreds Shopping centre, 3 supermarkets, pubs, clubs, arcades, The Embassy Theatre, the beach/ sea, Gibraltar Point. Two golf courses, Bowls green. Fun Fair etc... A garden (Not gated) which has a patio area and a collapsible washing line. Your own front door and drive which holds 3 cars. The kitchen has a double oven, induction hob, fridge/freezer, toaster, iron. Has WiFi

Guest favourite
Flat in Lincolnshire
5 out of 5 average rating, 8 reviews

Skegness centre close to beach, shops, beautiful

IDEALLY LOCATED IN THE HEART OF SKEGNESS 5 berth 2 bed beautiful large ground floor flat bath and shower free wifi tvs in 3 rooms dedicated work desk gas central heating all bedding and all towels included 4 poster kingsize bed/fireplace with fire/workdesk/smart tv all in main bedroom single bed/double bed/fire/smart tv in 2nd bedroom bath and large shower cubicle seperate toilet off road parking 2 mins to shops/pubs/amusements 5 mins to promenade large spacious, beautiful property

Top guest favourite
A modern lodge features a distinctive sloped roof made of wooden shingles. Large glass doors provide access to a spacious outdoor area, complemented by a stone pathway. Natural surroundings with green grass and trees can be seen in the background, reflecting a serene atmosphere.
Cabin in Hogsthorpe
4.98 out of 5 average rating, 150 reviews

Robin Lodge W/ Alpacas, Goats & Sheep | Wren Farm

Located at Wren Farm, our brand new to 2023 luxury lodges situated besides the alpaca fields, with Wren Farm Desserts cafe on site. Also near beaches, Skegness, Chapel, Mablethorpe, etc. We are dog friendly! Fully stocked (cutlery) Has 1 double bed and a sofa bed that sleeps 2. Private bathroom with shower. Surrounded by green fields, beautiful animals and excellent food! Add ons available on request - Ploughman's Grazing Box, Breakfast Boxes. Alpaca trekking also available.

Guest favourite
A modern glamping cabin is illuminated by soft outdoor lighting, showcasing a wooden exterior and a unique curved design. The spacious outdoor area includes a sheltered pergola with seating and a central chimney, creating a cozy ambiance against the twilight sky.
Cabin in Lincolnshire
4.95 out of 5 average rating, 105 reviews

Luxury Rural Cabin with Wood Fired Hot Tub

Crowtree by Wigwam Holidays is part of the UK's No1 glamping brand that has been providing guests with 'great holidays in the great outdoors' for over 20 years! Our site has 9 ensuite cabins, including 2 new Premium Cabins (no pets allowed in this cabin), and the capacity to accommodate for families, dogs and group bookings. Located near the banks of the River Welland in rural Lincolnshire, Crowtree by Wigwam Holidays offers a peaceful glamping retreat near Spalding.

Guest favourite
The exterior of the property features a two-story design with a welcoming entrance. A balcony extends from the upper level, providing outdoor space. The driveway leads to a secure entrance, while plants are positioned along the perimeter, offering a touch of greenery.
Home in Lincolnshire
4.83 out of 5 average rating, 24 reviews

3 Bed Detached Modern Seafront House Skegness

Make some memories at this unique and family-friendly place. Prime Sea front location close to the centre of Skegness and all the entertainment and fun activities this seaside town has to offer. Recently renovated property to a high standard. Open plan lounge kitchen diner upstairs with balcony with great views. 3 Bedrooms, 2 Double beds, 2 singles and sofa bed. Will sleep 8 if 2 are on sofa beds. 2 ensuite bathrooms. Parking at the front suitable for 1 car.

Top guest favourite
The exterior of a wooden beach hut is shown, framed by lush greenery. Bi-fold doors create a seamless entry, while steps lead up to the entrance. Sunlight filters through the trees, highlighting the natural wood finish and the tranquil surroundings.
Hut in Lincolnshire
4.95 out of 5 average rating, 37 reviews

Modern wooden cabin with beach views & access

Barefoot Beach Hut faces the North sea, with all its serenity and salt encrusted atmosphere. Standing alone, encased in greenery, this wooden hut offers picturesque beach views, while remaining nestled within the landscape, making it a perfect getaway for two. The concept behind its architecture is to immerse yourself in the harmonious surroundings, connecting with nature, while accompanied by home comforts. Offering the best balance between seclusion and adventure.

Popular amenities for Skegness holiday rentals

When is the best time to visit Skegness?

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Avg. price$151 SGD$149 SGD$143 SGD$140 SGD$140 SGD$141 SGD$163 SGD$187 SGD$142 SGD$137 SGD$134 SGD$134 SGD
Avg. temp5°C5°C7°C9°C12°C15°C17°C17°C15°C11°C7°C5°C

Frequently Asked Questions

  • What are the best places to stay in Skegness?

    Many visitors choose accommodations near the beach for easy access to the promenade and seaside. Neighborhoods around the town center and seafront are popular for staying close to shops, entertainment, and local dining.

  • What are the best things to do in Skegness with kids?

    Children often enjoy the funfair rides, interactive museums, and miniature railways. A day at the beach, exploring arcades, or spending time in local nature parks makes for a memorable family outing.

  • What are some of the best things to do in Skegness?

    Explore sandy beaches, enjoy classic amusement arcades, and visit local parks or gardens. Many guests stroll the pier, sample local food, and visit popular seafront entertainment venues.

  • How is the weather in Skegness?

    Skegness has cool, damp winters averaging 35–47°F (2–8°C), while summers reach 54–71°F (12–22°C) with light breezes. Rain is spread across the seasons, so bringing a waterproof layer is a good idea.

  • When is the best time to visit Skegness?

    Late spring through early fall is often recommended for milder weather and more open attractions. During summer months, temperatures usually reach around 54–71°F (12–22°C), with many seasonal events.

  • What are the best places to visit in Skegness?

    Explore the town’s beach, wander along the pier, or relax in well-maintained public gardens. The area has amusement centers, a local aquarium, and venues for live shows and performances.

  • What are some hiking trails in Skegness?

    You can explore coastal walking paths along the beach, nature reserves with marked trails, and footpaths in surrounding countryside. Many trails have gentle elevations and are suited for a range of abilities.

  • What are some family activities we can do in Skegness?

    Families frequently enjoy seaside arcades, mini-golf, and safe swimming areas during warmer weather. Parks, gardens, and interactive museums also make good outings for visitors with children.

  • What are some of the best day trip ideas from Skegness?

    Day trips to nearby nature reserves, market towns, or historic landmarks are frequently suggested. Visiting animal sanctuaries or exploring local countryside villages adds variety to your stay.

  • Are there any pet friendly accommodations available in Skegness?

    Skegness has pet friendly accommodations, especially in areas near the seafront and town parks. Look out for rentals that welcome dogs and provide easy access to outdoor walking spots.

  • What are some local tips for visiting Skegness?

    Dress in layers as weather by the coast changes quickly, and bring comfortable shoes for walking on sand and promenades. Booking attractions or accommodations ahead, especially during school holidays, is frequently suggested.

  • What is Skegness known for?

    Skegness is known for its sandy beaches, traditional amusement parks, and lively seafront. The area has a legacy of classic British seaside holidays, with a mix of arcades, beachfront gardens, and family attractions.

  • What are the best hidden gems to explore in Skegness?

    Explore quieter sections of the beach, locally run art galleries, and nature reserves around the town. Some visitors enjoy discovering small cafes and spots with murals or outdoor sculptures.

  • What are the best foods to try in Skegness?

    Fish and chips by the seaside are frequently suggested, along with locally made ice cream and traditional British pastries. Many cafes and seaside vendors highlight fresh seafood and classic comfort dishes.

  • What should I bring for a trip to Skegness?

    Pack layers for varying coastal temperatures, sturdy shoes, and a waterproof jacket in case of rain. Sun protection, a beach towel, and a camera are useful for seaside activities and exploring outdoor attractions.

  • What is the nightlife in Skegness like?

    Skegness has laid-back nightlife with pubs, cocktail bars, and some live music venues around the seafront and town center. You can explore casual spots for drinks, plus venues that host themed nights and tribute acts.

  • What are the most popular events or festivals in Skegness?

    Seasonal festivals, classic car rallies, and themed weekends draw crowds throughout the year. Summer often features open-air concerts and community celebrations along the seafront.

  • Are there family friendly vacation rentals in Skegness?

    Family friendly rentals are available near the beach and central neighborhoods, with easy access to parks, playgrounds, and attractions. Many properties have amenities supporting guests with children.

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