Skegness Holiday 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.

Skegness Holiday Cottages

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Your Skegness, Lincolnshire search returned 61 cottages

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Map View
An outdoor area with a cottage and gravel driveway at Denholme in Hogsthorpe
38
Hogsthorpe, Lincolnshire, PE24
  • Sleeps6
  • Bedrooms3
  • PetsYes

  • Sykes rating

Denholme, a pleasing single-storey house near the village of Hogsthorpe in Lincolnshire with blissful countryside views and a Smart TV. Chapel St Leonards 3 miles; Skegness 7.6 miles. (Ref. 1170861)

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


for 7 nights £535

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A brick semi detached house with large windows and a bench on a paved driveway at Chalfont Lodge in Skegness
60
Skegness, Lincolnshire, PE25
  • Sleeps18
  • Bedrooms9
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Chalfont Lodge is a stunning, nine-bedroom property residing in Skegness, Lincolnshire. Electric fire. Hot tub. En-suite bedrooms. EV charging. Boston 22.2 miles. (Ref. 1143154)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights £1692

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A dark exterior wall with two chairs and potted plants in front and an air conditioning unit at 19 The Court in Anderby Creek
37
Anderby Creek, Lincolnshire, PE24
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

19 The Court is a pleasing bungalow resting in Anderby Creek, Lincolnshire, boasting an open-plan layout, Smart TV and is a short walk to the beach. Chapel St Leonards 3.2 miles; Sandilands 3.8 miles; Ingoldmells 5.9 miles. (Ref. 1171646)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine


for 7 nights £428

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A sunroom with two wicker chairs facing the sea at Windyridge in Anderby Creek near Chapel St Leonards
39
Anderby Creek near Chapel St Leonards, Lincolnshire, PE24
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

Windyridge, a charming, detached cottage situated in the village of Anderby Creek on the golden Lincolnshire coast. WiFi. Sea views. Enclosed garden. Mablethorpe 7.7 miles; Skegness 9.7 miles. (Ref. 1154642)

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


for 7 nights £734

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The front of a dark blue house with a white porch and pebble driveway at 4 Roman Bank in Sutton-On-Sea
36
Sutton-On-Sea, Lincolnshire, LN12
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A detached single-storey cottage located in Sandilands near Sutton-On-Sea, Lincolnshire. En-suite bedrooms. Woodburning stove. Close to beach. Mablethorpe 4.1 miles; Ingoldmells 8.7 miles; Skegness 12.4 miles. (Ref. 1069237)

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


for 7 nights £557

Last booked yesterday
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A wooden cabin with a deck and umbrella surrounded by trees and plants at Kantankye Lodge Thorpe St Peter near Wainfleet All Saints
25
Thorpe St. Peter near Wainfleet All Saints, Lincolnshire, PE24
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Kantankye Lodge is a pleasant, single-storey lodge resting in Thorpe St. Peter, Lincolnshire. Off-road parking. Open-plan living. Dog-friendly. Burgh le Marsh 3.4 miles; Skegness 6.4 miles; Ingoldmells 8.7 miles. (Ref. 1140599)

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


for 7 nights £395

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Front view of a brick house with two white windows and a sliding glass door with plants on both sides at Monty's Retreat in Anderby Creek
31
Anderby Creek, Lincolnshire, PE24
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Monty’s Retreat is located in Anderby Creek near Skegness in Lincolnshire. Detached. Close to beach. Impressive views. Off-road parking. Dog-friendly. Chapel St Leonards 3.2 miles. Ingoldmells 5.9 miles. Skegness 9.7 miles. (Ref. 20242)

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


for 7 nights £531

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A front yard with a concrete driveway gravel areas a wooden picket fence a small shed and a brick house in the background at Bumble Bee Cottage in Skegness
22
Skegness, Lincolnshire, PE25
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Semi-detached, single-storey cottage located in the Lincolnshire town of Skegness. Pet-friendly. WiFi. Pretty enclosed garden. Off-road parking. Boston 22 miles. (Ref. 990946)

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


for 7 nights £314

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A brick bungalow with a paved driveway and a lawn at Waverley in Skendleby near Spilsby
38
Skendleby near Spilsby, Lincolnshire, PE23
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A single-storey cottage in an elevated position in the village of Skendleby near Spilsby, Lincolnshire. Walking opportunities. Linclonshire Wolds AONB location. Large garden. Spilsby 4.4 miles; Skegness 9.6 miles; Horncastle 12.8 miles. (Ref. 1038501)

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


for 7 nights £419

Last booked yesterday
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A brick building with solar panels on the roof near a pond and garden with a tree and flowers at Garden Cottage Great Steeping near Spilsby
18
Great Steeping near Spilsby, Lincolnshire, PE23
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Attractive, detached single-storey garden cottage in rural setting near Spilsby. Open plan, modern living area with woodburner. Flexible sleeping. Eco-friendly cottage with good walking and cycling. WiFi. Close to the coast. Spilsby 3 miles. (Ref. 930994)

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


for 7 nights £309

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A semi detached house with a lawn and hedge in front and a driveway on the side of the house at Beach Haven in Anderby Creek
38
Anderby Creek, Lincolnshire, PE24
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Beach Haven is a charming, contemporary home resting in Anderby Creek near Chapel St Leonards, Lincolnshire, with a hot tub and close by beach. Chapel St Leonards 3 miles; Skegness 9.4 miles; Lincolnshire Wolds National Landscape 26.7 miles. (Ref. 1149054)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights £748

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An outdoor area with brick walls and double doors at Angel's Retreat in Huttoft
17
Huttoft, Lincolnshire, LN13
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A pleasant, one-bedroom cottage resting in Huttoft, Lincolnshire. Near beach. Close to amenities. Pet-friendly. Anderby Creek 3.1 miles; Skegness 10.9 miles; Lincoln 40.2 miles. (Ref. 1094394)

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


for 7 nights £293

Last booked yesterday
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A house with a deck and fence in front at 3 Cherry Blossom in Skegness
20
Chapel St Leonards, Lincolnshire, PE24
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

3 Cherry Blossom is a charming, pet-friendly holiday chalet near a beach in Chapel St Leonards, Lincolnshire, with open-plan living and off-road parking. Skegness 5.8 miles; Mablethorpe 12.3 miles. (Ref. 1182474)

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


for 7 nights £314

Last booked yesterday
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A house with a red front door and garden at Marsh View Cottage in Wainfleet All Saints
23
Wainfleet All Saints, Lincolnshire, PE24
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A charming single-storey lodge tucked away on the outskirts of Wainfleet All Saints in Lincolnshire. Romantic retreat. Hot tub. Burgh le Marsh 5.4 miles; Skegness 5.8 miles; Ingoldmells 9.6 miles. (Ref. 1053346)

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


for 7 nights £421

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A single-story house with white and brick exterior walls and three windows at Jacobs Retreat in Anderby Creek near Chapel St Leonards
40
Anderby Creek near Chapel St Leonards, Lincolnshire, PE24
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Jacob's Retreat is a suitable, single-storey bungalow located along the coast in Anderby Creek near Chapel St Leonards in Lincolnshire enjoying lake views. Mablethorpe 9.2 miles; Skegness 9.7 miles. (Ref. 1163349)

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


for 7 nights £510

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A brick house with chimneys and a driveway next to a fenced garden at The Cottage in Burgh le Marsh
41
Burgh le Marsh, Lincolnshire, PE24
  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

This superb country cottage is based in Burgh le Marsh, Lincolnshire. Pet-friendly. WiFi. Open-plan living. Skegness 4 miles. (Ref. 997682)

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


for 7 nights £427

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A small black and white cabin with a white fence and black chairs on the porch at 114 Cherry Park in Chapel St Leonards
16
Chapel St Leonards, Lincolnshire, PE24
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

114 Cherry Park, a lovey, single-storey chalet set in the seaside village of Chapel St Leonards in Lincolnshire. Pet-friendly. Enclosed garden. Near beach. Skegness 5.9 miles; Mablethorpe 10.9 miles. (Ref. 1139541)

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


for 7 nights £315

Last booked 2 days ago
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A black cabin with large windows a white door and a white fence on a grassy lawn at 57 Cherry Park in Chapel St Leonards
22
Chapel St Leonards, Lincolnshire, PE24
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A contemporary, single-storey lodge resting in Chapel St Leonards, Lincolnshire. Open-plan. Smart TV. Electric fire. Off-road parking. Ingoldmells 2.2 miles; Skegness 5.3 miles; Mablethorpe 10.1 miles. (Ref. 1072248)

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


for 7 nights £356

Last booked yesterday
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A single story building with brick and gray wood siding with multiple windows and a tiled roof at The Stables in Wrangle near Old Leake
38
Wrangle near Old Leake, Lincolnshire, PE22
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A fabulous cottage converted from stables, set in Wrangle near Old Leake, Lincolnshire. Large garden. Countryside views. All-ground-floor. Boston 11.7 miles; Skegness 12.6 miles. (Ref. 1049681)

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

  • 10% off - Wed 1st Oct to 30th Nov 2025


for 7 nights £857

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A small house with a white railing and a patio set with an umbrella on a lawn at 19 Cherry Park in Chapel St Leonards
19
Chapel St Leonards, Lincolnshire, PE24
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A well-presented chalet located on Cherry Park in Chapel St Leonards, Lincolnshire. Open-plan living. Enclosed veranda. Smart TV. Skegness 5.9 miles; Mablethorpe 12.4 miles. (Ref. 1112030)

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


for 7 nights £413

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Map View

Located on the beautiful Lincolnshire coast is this collection of holiday cottages in Skegness. Skegness is a bustling seaside resort, well-loved by families, groups, couples and those alike, with a variety of attractions to keep all entertained.

Why Skegness Holiday Cottages?

Holiday cottages in Skegness take pride of place on the famous Lincolnshire coastline, they offer a fantastic seaside holiday destination with so much to see and do. Use your Skegness holiday cottage as a base to enjoy the pleasure beach with its long pier, as well as a host of attractions to suit all ages. Such attraction includes the Natureland Seal Sanctuary, Skegness Aquarium, and the imposing Jubilee Clock Tower.

Find more things to do during your stay at Skegness Holiday Cottages with our UK Travel Guide »

Places to Visit Near Holiday Cottages in Skegness

Skegness holiday cottages are perfectly positioned for enjoying the Lincolnshire coastline, as well as heading inland to explore the Lincolnshire Wolds AONB. Just a stone's throw away from Skegness is Ingoldmells, which is a popular coastal village, home to the theme park, Fantasy Island. Continue up the coastline and visit the coastal havens of, Chapel St Leonards, Louth, Market Rasen, Sutton-on-Sea, Woodhall Spa and Mablethrope for more beach days out.

Alternatively, use your cottages in Skegness as a base to explore inland, with the Lincolnshire Wolds waiting to be discovered. Here, you will find scenic paths and trails aplenty and opportunities to try your hand at archaeology, geology, and geocaching. Skegness holiday cottages are in an envious location with endless possibilities, with Norfolk, Lincoln, Cambridgeshire, Nottinghamshire, and Leicestershire resting within driving distance.

Other Popular Destinations near these Cottages in Skegness:

Chapel St Leonards

Sutton-on-Sea

Types of Lincolnshire Holidays

Now is the time to book a Skegness holiday cottage!

As well as superb holiday cottages in Skegness and pet-friendly cottages in Skegness, Lincolnshire offers a wide selection of holiday types. Looking to get away for the weekend?

Try these short breaks in Lincolnshire, while Lincolnshire hot tub breaks are ideal for a special getaway. Alternatively, try a Lincolnshire log cabin or Lincolnshire glamping pod for something unique! For the full collection, see Lincolnshire cottages.