Book Luxury Holiday Rentals in Cupar

Award-winning homes from £98

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Home spotlights in Cupar

Scottish Spirit

Scottish Spirit

  • 2 guests

  • 1 bedrooms

Penicuik and District, Midlothian

Tailor-made for two, this tranquil cottage promises a romantic retreat and true escape from it all. Set on an estate, you can wander the landscaped grounds at your leisure.

Sunshine on The Esk

Sunshine on The Esk

  • 10 guests

  • 5 bedrooms

Dalkeith, Scotland

Dating back to 1703, this former millhouse building has the charming appearance of a traditional country house, while the modern interiors and luxurious home comforts create an endlessly relaxing stay for large groups of friends or extended families looking to explore Edinburgh. Using the original raw materials of stone and wood to echo its heritage, and yet keeping things sleek and sophisticated with plenty of contemporary touches, the ground-floor sunroom is perhaps the best example of this beautifully balanced home.

Lady Macbeth

Lady Macbeth

  • 7 guests

  • 4 bedrooms

North Inch and Muirton, Perth

Overlooking North Inch Park and the River Tay, this classic apartment sits in a handsome, Georgian building. High ceilings, detailed cornicing and big sash windows all combine to create the feeling of stepping back into the 19th century inside.

The Jacobean Gatehouse

The Jacobean Gatehouse

  • 4 guests

  • 2 bedrooms

Colinsburgh and Kilconquhar, Fife

Nestled within Fife's Balcarres Estate, surrounded by some of Scotland's finest countryside, this historical home awaits. Dating back to the late 1800s, the redbrick facade and Jacobean style are truly charming, and many original features are still intact.


We selected the top 3% holiday homes in Cupar Holiday Rentals

Explore the 336 most perfect homes in our collection

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Most popular homes in Cupar

Where The Wildflowers Spring

Where The Wildflowers Spring

  • 4 guests

  • 2 bedrooms

Colinsburgh and Kilconquhar, Fife

Reclaim the Hills

Reclaim the Hills

  • 6 guests

  • 3 bedrooms

Dull and Weem, Perth and Kinross

The Coo's Tail

The Coo's Tail

  • 4 guests

  • 2 bedrooms

Spittalfield and District, Perth and Kinross

The Crown

The Crown

  • 4 guests

  • 2 bedrooms

Gullane Area, East Lothian

Beside the Farmhouse

Beside the Farmhouse

  • 10 guests

  • 5 bedrooms

Aberfeldy, Perth and Kinross

Fashion & Fire

Fashion & Fire

  • 4 guests

  • 2 bedrooms

St Andrews, Fife

Where The Stravaigers Go

Where The Stravaigers Go

  • 2 guests

  • 1 bedrooms

Colinsburgh and Kilconquhar, Fife

Shepherd's Watch

Shepherd's Watch

  • 4 guests

  • 2 bedrooms

Oxton and Channelkirk, Scottish Borders

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Cupar. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Cupar has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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