Book Luxury Holiday Rentals in Cupar

Award-winning homes from £98

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Age 13+

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Age 1 to 12

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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.

Highland Games

Highland Games

  • 9 guests

  • 4 bedrooms

Auchterarder and District, Perth and Kinross

Set in the dramatic countryside of Perthshire, where the Scottish highlands begin, this home is the ultimate rural retreat. It’s all fun and games on the ground floor where a hot tub sits in a turret, surrounded by windows looking out over the wilderness.

All Right Now

All Right Now

  • 33 guests

  • 15 bedrooms

Blairgowrie, Scotland

This enchanting, stone-built manor is the perfect venue for large family holidays, corporate getaways or celebration weekends, accommodating up to thirty-three guests in fifteen en-suite bedrooms. The property boasts a vast function room with a bar that leads onto an elegant patio with outdoor seating and a pretty bandstand suitable for an outdoor wedding.

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 350 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

Shepherd's Watch

Shepherd's Watch

  • 4 guests

  • 2 bedrooms

Oxton and Channelkirk, Scottish Borders

Brambled Bliss

Brambled Bliss

  • 2 guests

  • 1 bedrooms

Penicuik and District, Midlothian

Doorway To Elphame

Doorway To Elphame

  • 16 guests

  • 7 bedrooms

Musselburgh and Inveresk, Scotland

Sweet Morning

Sweet Morning

  • 4 guests

  • 2 bedrooms

King's Park, Stirling

Pheasant Grove

Pheasant Grove

  • 12 guests

  • 6 bedrooms

Auchtermuchty and Strathmiglo, Fife

Where The Stravaigers Go

Where The Stravaigers Go

  • 2 guests

  • 1 bedrooms

Colinsburgh and Kilconquhar, Fife

Graceful Grove

Graceful Grove

  • 2 guests

  • 1 bedrooms

Penicuik and District, Midlothian

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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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