Book Luxury Monthly Rentals in Cupar

We selected the 350 homes worth renting in this location

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Home spotlights in Cupar

Garden of Tranquillity

Garden of Tranquillity

  • 2 guests

  • 1 bedrooms

Penicuik and District, Midlothian

Built in 1714, this historic home makes the perfect setting for a magical stay in Scotland. You’ll be serenaded by an abundance of charm and character as well as a range of luxurious features.

Flock Of Sheep

Flock Of Sheep

  • 5 guests

  • 2 bedrooms

Oxton and Channelkirk, Scottish Borders

Escape to the rural idyll of farmhouse life at this cosy cottage in the Lauderdale Hills. It’s on a working farm, where the sheep have been tended to by the same family for generations and you can ramble across hilltops and country lanes straight from your doorstep.

The Coo's Tail

The Coo's Tail

  • 4 guests

  • 2 bedrooms

Spittalfield and District, Perth and Kinross

Apart from the odd bleat of a sheep or moo of a coo, there’s not much else to disturb the peace at this spot in the Perthshire countryside. Fields stretch before you (check out the view from the balcony), yet it’s just three miles to the charming market town of Dunkeld to stock up on supplies and try the local cafes.

A Midsummer's Song

A Midsummer's Song

  • 10 guests

  • 5 bedrooms

Stirling, Scotland

Introducing a unique and modernized farmhouse conversion, the Outlander Estate offers an impressive 5-bedroom holiday rental just outside Stirling, Scotland. Nestled in a tranquil setting with views of Stirling Castle, this property provides a perfect base for exploring the area's historic sites and amenities.


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

Explore the 350 most perfect homes in our collection

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Most popular homes in Cupar

The Little Love Song

The Little Love Song

  • 4 guests

  • 2 bedrooms

Colinsburgh, Leven

The Highland Home

The Highland Home

  • 4 guests

  • 2 bedrooms

Edinburgh, Scotland

Reclaim the Hills

Reclaim the Hills

  • 6 guests

  • 3 bedrooms

Dull and Weem, Perth and Kinross

Scottish Spirit

Scottish Spirit

  • 2 guests

  • 1 bedrooms

Penicuik and District, Midlothian

Highland Games

Highland Games

  • 9 guests

  • 4 bedrooms

Auchterarder and District, Perth and Kinross

All Right Now

All Right Now

  • 33 guests

  • 15 bedrooms

Blairgowrie, Scotland

The Jacobean Gatehouse

The Jacobean Gatehouse

  • 4 guests

  • 2 bedrooms

Colinsburgh and Kilconquhar, Fife

Where The Wildflowers Spring

Where The Wildflowers Spring

  • 4 guests

  • 2 bedrooms

Colinsburgh and Kilconquhar, Fife

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Cupar, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Cupar Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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