Fife Cottage Holidays

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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.

Popular property types See all properties

Pet friendly

16 properties

Properties with hot tubs

3 properties

Luxury

1 property

Log cabins

1 property

Properties with character

13 properties

Remote

1 property

Fife Cottage Holidays

REFINE SEARCH

Your Fife search returned 31 cottages

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Map View
A wooden lodge with a black deck and stairs leading to the entrance surrounded by grass and gravel at Eden Fields Lodge in Cupar Fife
30
Cupar, Fife, Fife, KY15
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

This charming, two-bedroom holiday lodge rests in Cupar, Fife. Smart TV. Electric fire. Family-friendly. Off-road parking. Open-plan. St Andrews 10.6 miles; Kirkcaldy 16 miles (Ref. 1134482)

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

7 nights from £537

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A stone and stucco cottage with a gravel driveway and garden plants at Katmoget Cottage in Scotstarvit near Ceres
26
Scotstarvit near Ceres, Fife, KY15
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

This homely, single-storey holiday home rests in the quaint hamlet of Scotstarvit near Ceres, Fife. Off-road parking. Ground-floor living. Enclosed garden. Washing machine. Cupar 2.7 miles; Leven 7.7 miles; Fife 9.4 miles; St Andrews 9.9 miles. (Ref. 1138207)

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

7 nights from £405

Last booked 2 days ago
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A living room with floral wallpaper a fireplace a TV armchairs and a coffee table at Wonderland Cottage in Newburgh Fife
34
Newburgh, Fife, Fife, KY14
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A quirky and idyllic mid-terrace cottage lying in the heart of Newburgh, Scotland. characterful features. Woodburning stove. Close to amenities. Perth 11.3 miles; Dundee 19.5 miles; St Andrews 20.2 miles. (Ref. 1069288)

  • Wi-fi
  • Washing machine

7 nights from £411

Last booked 2 days ago
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Exterior view of a white pebble dash bungalow with black door and windows flower pots and outdoor seating at Seascape in Kinghorn
20
Kinghorn, Fife, KY3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A fabulous coastal chalet nestled in the town of Kinghorn, Fife. Open-plan living. Accessible accommodation. Beachfront setting. Kirkcaldy 4 miles; Dunfermline 13.5 miles; St Andrews 28 miles. (Ref. 1072897)

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

7 nights from £631

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A front garden with bushes and grass in front of a brick house at 48 Edenbank Road in Cupar Fife
25
Cupar, Fife, Fife, KY15
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A single-storey welcoming cottage resting in Cupar, in Fife. Child and pet-friendly. Close to amenities and attractions. Ground-floor living. Enclosed garden. St Andrews 9.7 miles; Kirkcaldy 18.1 miles. (Ref. 1108043)

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

7 nights from £406

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A stone house with six windows three barrels and a green door at 40 Main Street in Aberdour
20
Aberdour, Fife, KY3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A stunning, first-floor apartment resting in Aberdour, Fife. Off-road parking. Near beach. Close to amenities. Family-friendly. Edinburgh 19.7 miles; Stirling 30.4 miles; St Andrews 35.7 miles. (Ref. 1080106)

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

7 nights from £361

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An outdoor patio with seating and potted plants outside a building with white walls and black window frames at Fishers Rest in Anstruther
32
Anstruther, Fife, KY10
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

This lovely, terraced, reverse-level cottage sits on a courtyard in Anstruther, Fife. Sea views. Pet-friendly. Off-road parking. Smart TV. Family-friendly. Close to amenities. St Andrews 9.7 miles; Cupar 16.5 miles; Edinburgh 50.3 miles. (Ref. 1101768)

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

7 nights from £935

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A street view of connected houses with flower pots and a green bin outside at Rosedale in Falkland
35
Falkland, Fife, KY15
  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A well-presented, four-bedroom home resting in Falkland, Fife. Family and pet-friendly. Close to amenities. Enclosed garden with hot tub. Ground-floor living. Perth 17 miles; St Andrews 20.1 miles; Dundee 23.8 miles. (Ref. 1127674)

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

7 nights from £818

Last booked 6 hours ago
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A street view with a stone and white building with tiled roof next to a clock tower at Dunira in Falkland
35
Falkland, Fife, KY15
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A detached cottage nestled within the centre of the idyllic village of Falkland. Woodburning stove. Central location. Contemporary interior. Kirkcaldy 11 miles. St Andrews 20 miles. (Ref. 977313)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £552

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Exterior view of a white two-story house with red tiled roof and stone wall in front at Sandpipers in Crail
20
Crail, Fife, KY10
  • Sleeps5
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

This detached cottage is based in Crail, Scotland. 2 bedrooms. Modern furnishings. St. Andrews 10 miles; Dundee 22 miles. (Ref. 990743)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £474

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An outdoor hot tub with water in a courtyard surrounded by stone buildings and trees at The Stables in Cupar Fife
New property
37
Cupar, Fife, Fife, KY15
  • Sleeps6
  • Bedrooms3
  • PetsNo

  • Sykes rating

The Stables is an exquisite holiday home near Cupar, Fife, boasting ground-floor living alongside a private hot tub to enjoy in the front garden courtyard. St Andrews 8.8 miles. (Ref. 1174213)

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

7 nights from £639

Last booked yesterday
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A street view of a residential building with windows and a door with plants outside on Back Street at Lower Neuk in Culross
22
Culross, Fife, KY12
  • Sleeps4
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Lowe Neuk is a fine, ground-floor apartment nesting in the unique village of Culross, near Kincardine, Fife. Close to beach. Roadside parking. Open fire (Ref. 1125861)

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

7 nights from £487

Last booked yesterday
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A stone cottage with green door and windows surrounded by grass and trees with outdoor table and chairs in front at Middle Cottage - Tarvit in Cupar Fife
30
Cupar, Fife, Fife, KY15
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

A delightful ground floor cottage resting within the enchanting grounds of Hill of Tarvit Mansion in Cupar, Scotland. Open fire. Single-storey. Dog-friendly. St Andrews 9.5 miles; Kirkcaldy 16.2 miles; Perth 25.8 miles. (Ref. 1060390)

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

7 nights from £634

Last booked 2 days ago
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A large house with striped lawns and trees in the background at Upper West Wing Flat - Tarvit in Cupar Fife
20
Cupar, Fife, Fife, KY15
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A grand and elegant first floor apartment within the Hill of Tarvit Mansion, lying in Cupar, Scotland. Romantic. Off-road parking. Open fire. St Andrews 9.5 miles; Kirkcaldy 16.2 miles; Perth 25.8 miles. (Ref. 1060391)

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

7 nights from £424

Last booked yesterday
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A cottage with white walls and a dark roof surrounded by a lawn and trees at West Cottage - Tarvit in Cupar Fife
31
Cupar, Fife, Fife, KY15
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

This delightful ground floor cottage lies on the grounds of Hill of Tarvit Mansion, in Cupar, Scotland. Open fire. Enclosed private garden. Utility. Dog-friendly. St Andrews 9.5 miles; Kirkcaldy 16.2 miles; Perth 25.8 miles. (Ref. 1060392)

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

7 nights from £658

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A living room with a plaid sofa and wooden coffee table near a fireplace at Invermay in Pittenweem
28
Pittenweem, Fife, KY10
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A wonderful duplex apartment resting on the seafront in Pittenweem, Fife. Woodburning stoves. Ideal for couples. Sea views. Anstruther 1.6 miles; St Andrews 10.8 miles. (Ref. 1064091)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £792

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An exterior stairway leading to a wooden door with metal railing on a white textured building at Flourloft in Pittenweem
17
Pittenweem, Fife, KY10
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Superb harbourside apartment in Pittenweem, in Fife’s beautiful East Neuk. Quality, well-equipped comfortable accommodation. En-suite facilities. Harbourside location near village's shops, bars and galleries. (Ref. 924733)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £424

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The entrance to a cottage with a white door a window to the left and a red tile roof at Rhum Cottage Peat Inn near St Andrews
17
Peat Inn near St Andrews, Fife, KY15
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

A charming ground-floor cottage nestled in the tranquil village of Peat Inn near Ceres, Fife. Pet friendly. Woodburning stove. Quiet location. St Andrews 6.3 miles; Cupar 6.5 miles; Leven 9.6 miles. (Ref. 1057899)

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

7 nights from £476

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A single story house with a red tiled roof two black chairs and a small table outside and hanging flower baskets at Shore View in Kinghorn
17
Kinghorn, Fife, KY3
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A stunning beachfront chalet positioned on the shores of Kinghorn, Scotland. Open-plan living. Ideal for couples. Off-road parking. Kirkcaldy 4 miles; Dunfermline 13.4 miles; St Andrews 28 miles. (Ref. 1072894)

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

7 nights from £626

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Stone exterior of a townhouse with windows a bench and a white door at Maimie's Harbourview in Pittenweem near Anstruther
24
Pittenweem near Anstruther, Fife, KY10
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

This semi-detached cottage is based in the fishing village of Pittenweem, Scotland. WiFi. Enclosed garden. St Andrews 10 miles; Cupar 16 miles. Roadside parking (Ref. 1006885)

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

7 nights from £635

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Map View

This charming selection of self-catering cottages rests in the historic county of Fife, also known as the Kingdom of Fife. Bring your loved ones to enjoy a break amongst stunning backdrops at any time of year in these Fife cottages.

Why Fife Cottages?

These holiday cottages in Fife offer a wonderful holiday destination with activities for all ages. The main attraction in Fife, certain to entice any golf enthusiasts, is the spectacular town of St Andrews, known to many as the 'Home of Golf' for its range of courses and the iconic 'Old Course'. Walkers and cyclists will not be left short while staying in holiday cottages in Fife, with the Fife Coastal Path and varying terrains to discover, as well as there being other activities including theatres, fishing and water sports in the area. Find more inspiration for your next break in the Scotland Travel Guide.

Places to Visit near Holiday Cottages in Fife

Along with Fife holidays, a fantastic holiday with the whole family can be found in Perth, Angus and the quintessentially Scottish county of Aberdeenshire, famous for its whiskey distilleries and grand castles.

There are even more locations to uncover near Fife holidays, including:

St Andrews

Scottish Highlands

Perthshire

Types of Scottish Holidays

Looking for more getaways in this magnificent country? Browse this bigger selection of Scotland holidays instead. There are plenty of self-catering Fife cottages to tickle your fancy no matter what you're looking for. Bring your beloved pooch along with you with this collection of dog friendly cottages in Scotland, or celebrate your most special occasions with these luxury cottages in Scotland.

With breath-taking scenery to savour in this striking area, what better way to immerse yourself than with a break in lodges and log cabins in Scotland, If lodges and log cabins aren't quite your style, you still have the option for hot tub holidays in Scotland and you can even book a fun-filled seaside break with these coastal cottages in Scotland.