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Rural luxury holiday homes in Cupar between St Andrews and Dundee

Nestled in rolling Fife countryside, Cupar is a historic market town perfect for exploring Scotland's agricultural heartland. Stay in luxury country estates and farmhouses surrounded by gentle hills, charming hamlets, and riverside walks that capture authentic rural Scottish charm.

Wake each day to scenic views and explore nearby St Andrews, the East Neuk coastal villages, and picturesque Falkland. Our curated collection includes grand estates and peaceful country homes ideal for those seeking peaceful countryside escape.

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Family Friendly Vacation Rental - Relax and create unforgettable moments on the patio, complete with BBQ facilities and a lush, spacious garden

Bowhill Luxury Retreat

Cupar

  • Bedrooms 5
  • Sleeps 10
Golfing Experience in a Holiday Home - Pristine golf course, featuring rolling greens and a tranquil setting for an exceptional golfing experience

Hawkswood Country Estate

Cupar

  • Bedrooms 15
  • Sleeps 30
Private Hot Tub in a Vacation Rental - Luxurious private hot tub, perfect for relaxation with serene surroundings and ultimate comfort

Hawkswood House

Cupar

  • Bedrooms 5
  • Sleeps 10
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The Roundel

Cupar

  • Bedrooms 5
  • Sleeps 10
(4 matches)
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Great for…
Property type
Facilities
  • Main Door
  • En-suite bathroom(s)
  • Dishwasher
  • Cot / Travel cot
  • High Chair
  • Coffee Machine
  • Bath
  • Hot Tub / Jacuzzi
  • Wood-burning Stove
Outdoor
  • Balcony
  • Garden dining furniture
  • Private garden
  • Private courtyard
  • Patio / decking
Parking
  • Free parking (outdoor)
Pets
  • Pets allowed
All our stays include:
  • Linen and towels
  • WiFi
  • Washing machine
  • Iron and ironing board
  • Fridge/freezer
  • Personal meet and greet available
  • Hairdryer