Book Luxury Holiday Rentals in Cupar

Award-winning homes from £98

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Home spotlights in Cupar

Scottish Tranquillity

Scottish Tranquillity

  • 8 guests

  • 4 bedrooms

Penicuik and District, Midlothian

Once the home to the estate’s Head Gardener, this Midlothian home is the perfect bolthole for a family on a back-to-nature retreat. We love the sense of history this home offers, along with all the modern touches you’d want for a relaxing stay.

Highland Hymn

Highland Hymn

  • 2 guests

  • 1 bedrooms

Penicuik and District, Midlothian

On the outside, this 18th-century barn conversion is rustic as can be. But step through the door and you'll be transported into a serene Scandinavian-inspired space – appropriate, given guests enjoy a private session in the shared Finnish sauna.

Sweet Morning

Sweet Morning

  • 4 guests

  • 2 bedrooms

King's Park, Stirling

Located in the prestigious Kings Park area of Stirling, this recently refurbished property offers a bright and modern self-catering experience. Situated on the garden floor of a converted Victorian villa, it provides privacy and tranquility with its lush trees and stone walls.

Fisherman's Shanty

Fisherman's Shanty

  • 2 guests

  • 1 bedrooms

Pittenweem, Fife

New York loft-style meets traditional fishing cottage at this bijou home in Pittenweem. Stepping inside, you can see this place was designed by an award-winning architect.


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

Explore the 338 most perfect homes in our collection

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Most popular homes in Cupar

The Jacobean Gatehouse

The Jacobean Gatehouse

  • 4 guests

  • 2 bedrooms

Colinsburgh and Kilconquhar, Fife

Shepherd's Watch

Shepherd's Watch

  • 4 guests

  • 2 bedrooms

Oxton and Channelkirk, Scottish Borders

Everything is A-OK

Everything is A-OK

  • 5 guests

  • 2 bedrooms

North Berwick, Scotland

The Glittering Stone

The Glittering Stone

  • 3 guests

  • 2 bedrooms

Cambusbarron, Stirling

Doorway To Elphame

Doorway To Elphame

  • 16 guests

  • 7 bedrooms

Musselburgh and Inveresk, Scotland

Under Lock & Key

Under Lock & Key

  • 6 guests

  • 3 bedrooms

Kinghorn, Fife

Where The Stravaigers Go

Where The Stravaigers Go

  • 2 guests

  • 1 bedrooms

Colinsburgh and Kilconquhar, Fife

Rest for the Soul

Rest for the Soul

  • 4 guests

  • 2 bedrooms

Kelty, Fife

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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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